International Union of Pure and Applied Chemistry

Division VIII Chemical Nomenclature and Structure Representation Division

Table of Contents of
Nomenclature of Organic Chemistry.
IUPAC Recommendations and Preferred Names 2013.

Prepared for publication by Henri A. Favre and Warren H. Powell, Royal Society of Chemistry, ISBN 978-0-85404-182-4

World Wide Web version Prepared by G. P. Moss
School of Biological and Chemical Sciences, Queen Mary University of London,
Mile End Road, London, E1 4NS, UK

1    P-1General Principles, Rules, and Conventions
130    P-2Parent Hydrides
372    P-3Characteristic (functional) and Substituent Groups
428    P-4Rules for Name Construction
552    P-5Selecting Preferred IUPAC Names and Constructing Names of Organic Compounds
648    P-6Applications to Specific Classes of Compounds
1048    P-7Radicals, Ions, and Related Species
1130    P-8Isotopically Modified Compounds
1156    P-9Specification of Configuration and Conformation
1293    P-10Parent Structures for Natural Products and Related Compounds
xxvii   Preface
xxix       1.Scope of the recommendations in the 2012 edition
xxix       2.Skeletal replacement (‘a’) nomenclature
xxix       3.Substitutive nomenclature
xxx       4.Multiplicative nomenclature
xxxi       5.Hydro or dehydro prefixes
xxxi       6.Suffixes
xxxi       7.Prefixes
xxxiii       8.Locants
xxxiv       9.Acyclic systems
xxxiv       10.Hantzsch-Widman system
xxxiv       11.Polycyclic ring systems
xxxv       12.Seniority
xxxvi       13.Adducts
xxxvi       14.Enclosing marks
xxxvi       15.Esters
xxxvii       16.Amides
xxxvii       17.Inorganic parent structures
xxxvii       18.Radicals and ions
xxxviii       19.Isotopically modified compounds
1   P-10Introduction
2   P-11Scope of nomenclature for organic compounds
3   P-12Preferred, Preselected, and Retained IUPAC Names
3       P-12.1Preferred IUPAC Names
8       P-12.2Preselected Names
9       P-12.3Retained Names
9       P-12.4Methodology
10   P-13Operations in Nomenclature of Organic Compounds
10       P-13.1The Substitutive Operation
10       P-13.2The Replacement Operation
13       P-13.3The Additive Operation
13           P-13.3.1    By an additive prefix
15           P-13.3.2    By an additive suffix
15           P-13.3.3    By a separate word
17       P-13.4The Subtractive Operation
17           P-13.4.1    By a suffix
17           P-13.4.2    By a change in ending
18           P-13.4.3    By the prefixes ‘dehydro’ and ‘nor’
19       P-13.5The Conjunctive Operation
19           P-13.5.1    By placing a multiplicative prefix ‘bi’, ‘ter’, ‘quater’, etc.
20           P-13.5.2    By juxtaposition of component names (conjunctive nomenclature)
20           P-13.5.3    Ring formation
21       P-13.6The Multiplicative Operation
22       P-13.7The Fusion Operation
23       P-13.8Operations Used Only in the Nomenclature of Natural Products
23           P-13.8.1    By the prefixes ‘de’ and ‘des’
24           P-13.8.2    By the prefix ‘anhydro’
25   P-14General Rules
25       P-14.0Introduction
25       P-14.1Bonding Number
26           P-14.1.1    Definition
26           P-14.1.2    Standard bonding numbers
26           P-14.1.3    Nonstandard bonding numbers (λ-convention)
27       P-14.2Multiplicative Prefixes
27           P-14.2.1    Basic multiplicative prefixes
28           P-14.2.2    Numerical terms for compound or complex features
28           P-14.2.3    Multiplicative prefixes for naming assemblies of identical units
28       P-14.3Locants
28           P-14.3.1    Types of locants
29           P-14.3.2    Position of locants
29           P-14.3.3    Citation of locants
30           P-14.3.4    Omission of locants
34           P-14.3.5    Lowest set of locants
34       P-14.4Numbering
41       P-14.5Alphanumerical Order
42           P-14.5.1    Simple prefixes
43           P-14.5.2    The name of a prefix for a substituent
44           P-14.5.3    When an alphanumerical ordering is required
44           P-14.5.4    When two or more prefixes consist of identical Roman letters
45       P-14.6Nonalphanumerical Order
47       P-14.7Indicated and ‘Added Indicated’ Hydrogen
47           P-14.7.1    Indicated hydrogen
47           P-14.7.2    ‘Added indicated hydrogen’
48       P-14.8Adducts
48           P-14.8.1    Organic adducts
52           P-14.8.2    Mixed organic – inorganic adducts
53   P-15Types of Nomenclature
54       P-15.0Introduction
55       P-15.1Substitutive Nomenclature
55           P-15.1.1    Parent hydrides
55           P-15.1.2    Functional parent compounds
56           P-15.1.3    Suffixes
57           P-15.1.4    Position of the endings ‘ane’, ‘ene’, and ‘yne’
57           P-15.1.5    Prefixes and their order in names
58           P-15.1.6    Other components of substitutive names
58           P-15.1.7    Construction of substitutive names
62           P-15.1.8    Substitution rules for parent structures with retained names
65       P-15.2Functional Class Nomenclature
65           P-15.2.0    Introduction
66           P-15.2.1    Functional class nomenclature using substituent group names
67           P-15.2.2    Functional class nomenclature using functional modifiers
68           P-15.2.3    Seniority of functional classes
68           P-15.2.4    Polyfunctional compounds
69       P-15.3Multiplicative Nomenclature
69           P-15.3.0    Introduction
70           P-15.3.1    General methodology
76           P-15.3.2    Construction of multiplicative names
85           P-15.3.3    Identical structural units linked by unsymmetrical multiplicative groups
86           P-15.3.4    Limitations of multiplicative nomenclature
89       P-15.4Skeletal Replacement (‘a’) Nomenclature
89           P-15.4.0    Introduction
89           P-15.4.1    General rules
91           P-15.4.2    Skeletal replacement (‘a’) nomenclature
91           P-15.4.3    Skeletal replacement (‘a’) nomenclature for acyclic parent hydrides
94       P-15.5Functional Replacement Nomenclature
94           P-15.5.1    Definition
94           P-15.5.2    General methodology
94           P-15.5.3    Scope of functional replacement nomenclature
98       P-15.6Conjunctive Nomenclature
98           P-15.6.1    Name formation
102           P-15.6.2    Limitations of conjunctive nomenclature
103           P-15.6.3    Analysis of conjunctive name construction
104   P-16Name Writing
104       P-16.0Introduction
104       P-16.1Spelling
105       P-16.2Punctuation
105           P-16.2.1    Commas
105           P-16.2.2    Full stops
105           P-16.2.3    Colons and semicolons
105           P-16.2.4    Hyphens
106           P-16.2.5    Spaces
107       P-16.3Multiplicative prefixes ‘di’, ‘tri’, etc. vs. ‘bis’, ‘tris’, etc.
107           P-16.3.1    Multiplicative prefixes
107           P-16.3.2    General methodology
107           P-16.3.3    The basic numerical prefixes ‘di’, ‘tri’, ‘tetra’, etc.
109           P-16.3.4    Parentheses (round brackets)
110           P-16.3.5    The numerical prefixes ‘bis’, ‘tris’, ‘tetrakis’, etc.
111           P-16.3.6    The prefixes ‘bis’, ‘tris’, ‘tetrakis’, etc.
113       P-16.4Other Numerical Terms
113           P-16.4.1    The numerical prefixes ‘bi’, ‘ter’, ‘quater’, etc.
113           P-16.4.2    The prefix ‘mono’
113           P-16.4.3    The term ‘sesqui’
113       P-16.5Enclosing Marks
114           P-16.5.1    Parentheses (also called curves or round brackets)
118           P-16.5.2    Brackets (also called square brackets)
119           P-16.5.3    Braces (also called curly brackets)
119           P-16.5.4    Multiple types of enclosing marks
121       P-16.6Italicization
121           P-16.6.1    Lower case italic letters
121           P-16.6.2    Italicized elements symbols, such as O, N, As
121           P-16.6.3    The italic element symbol H
121           P-16.6.4    Italic terms, syllables, and capital Roman letters
122       P-16.7Elision of Vowels
122           P-16.7.1    Vowels systematically elided
123           P-16.7.2    There is no elision of terminal vowels
124       P-16.8Addition of Vowels
124           P-16.8.1    For euphonic reasons (the vowel ‘o’)
124           P-16.8.2    For euphonic reasons (the letter ‘a’)
124       P-16.9Primes
124           P-16.9.1    Primes (′), double primes (′′), triple primes (′′′), etc., with nitrogen
125           P-16.9.2    Superscript arabic numbers,
126           P-16.9.3    Primes (′), double primes (′′), triple primes (′′′), etc., with superscripted numerical locants
128           P-16.9.4    Primes (′), double primes (′′), triple primes (′′′), etc., used to differentiate identical locants
129           P-16.9.5    Other uses of primes
addition           P-16.9.6    Multiple primes
130   P-20Introduction
131   P-21Mononuclear and Acyclic Polynuclear Parent Hydrides
131       P-21.1Mononuclear Parent Hydrides
131           P-21.1.1    Mononuclear parent hydrides with standard bonding numbers
133           P-21.1.2    Mononuclear parent hydrides with nonstandard bonding numbers
133       P-21.2Acyclic Polynuclear Parent Hydrides
133           P-21.2.1    Hydrocarbons
134           P-21.2.2    Homogeneous acyclic parent hydrides other than hydrocarbons and boron hydrides
135           P-21.2.3    Heterogenous acyclic parent hydrides
136           P-21.2.4    Acyclic parent hydrides containing heteroatoms with nonstandard bonding numbers
137   P-22Monocyclic Parent Hydrides
137       P-22.1Monocyclic Hydrocarbons
137           P-22.1.1    Saturated monocyclic hydrocarbons
137           P-22.1.2    Unsubstituted monocyclic hydrocarbon polyenes
139           P-22.1.3    Parent hydrocarbons having retained names
139       P-22.2Heteromonocyclic Parent Hydrides
140           P-22.2.1    Retained names of heteromonocycles
143           P-22.2.2    Heteromonocyclic parent hydrides with 3-10 membered rings (Hantzsch-Widman names)
148           P-22.2.3    Heteromonocyclic parent hydrides named by skeletal replacement (‘a’) nomenclature
150           P-22.2.4    Heteromonocycles with eleven or more members with the maximum number of noncumulative double bonds
151           P-22.2.5    Homogeneous monocyclic parent hydrides other than boron hydrides
152           P-22.2.6    Heteromonocyclic parent hydrides composed of repeating heterounits
153           P-22.2.7    Heteromonocyclic parent hydrides having heteroatoms with nonstandard bonding numbers
155   P-23Polyalicyclic Parent Hydrides (Extended von Baeyer System)
155       P-23.0Introduction
155       P-23.1Definitions and Terminology
156       P-23.2Naming and Numbering of von Baeyer Hydrocarbons
156           P-23.2.1    Selection of the main ring
156           P-23.2.2    Naming bicyclic alicyclic hydrocarbons
157           P-23.2.3    Numbering bicyclic alicyclic hydrocarbons
157           P-23.2.4    Selection of the main bridge
157           P-23.2.5    Naming and numbering tricyclic alicyclic hydrocarbons
158           P-23.2.6    Naming and numbering polyalicyclic hydrocarbons
158             P-        Naming polycyclic alicyclic hydrocarbons
159             P-        Selection of the main bridge and secondary bridges
162             P-        Numbering of secondary bridges
164             P-        If there is a further choice for numbering the secondary bridges
164       P-23.3Heterogeneous Heterocyclic von Baeyer Parent Hydrides
164           P-23.3.1    Heterogeneous heterocyclic von Baeyer systems
165           P-23.3.2    When there is a choice for numbering
165       P-23.4Homogeneous Heterocyclic von Baeyer Parent Hydrides
166       P-23.5Heterogeneous Heterocyclic von Baeyer Parent Hydrides Composed of Alternating Heteroatoms
166           P-23.5.1    Heterogeneous von Baeyer systems composed of alternating skeletal heteroatoms
167           P-23.5.2    The prefixes ‘Si-’ or ‘N-’ preceded by the italic number ‘1’
168           P-23.5.3    Silasesquioxanes, silasesquithianes, etc.
168       P-23.6Heterocyclic Polyalicyclic Parent Hydrides having Heteroatoms with Nonstandard Bonding Numbers
168           P-23.6.1    The λ-convention
168           P-23.6.2    When there is a choice for numbering
169       P-23.7Retained Names for von Baeyer Parent Hydrides
169   P-24Spiro Ring Systems
169       P-24.0Introduction
170       P-24.1Definitions
170       P-24.2Spiro Ring Systems with only Monocyclic Ring Components
170           P-24.2.0    Introduction
171           P-24.2.1    Monospiro alicyclic ring systems
171           P-24.2.2    Linear polyspiro alicyclic ring systems
173           P-24.2.3    Branched polyspiro alicyclic ring systems
175           P-24.2.4    Heterocyclic spiro ring systems
178       P-24.3Monospiro Ring Systems Containing Two Identical Polycyclic Ring Components
178           P-24.3.1    Monospiro ring systems consisting of two identical polycyclic ring components
179           P-24.3.2    Where appropriate the maximum number of noncumulative double bonds
180           P-24.3.3    If there is a choice for assigning primed locants
181           P-24.3.4    Heterocyclic ‘spirobi’ ring systems named by skeletal replacement (‘a’) nomenclature
182       P-24.4Dispiro Ring Systems with Three Identical Polycyclic Ring Components Spirofused Together
182           P-24.4.1    Dispiro ring systems with three identical polycyclic ring components
182           P-24.4.2    If there is a choice for locants
183           P-24.4.3    Three identical heterocyclic ring components spirofused together
184       P-24.5Monospiro Ring Systems with Different Components, at least One of which is a Polycyclic Ring System
184           P-24.5.1    Monospiro ring systems with different ring components
185           P-24.5.2    Monospiro ring systems with different ring components at least one being a polycyclic ring and at least one ring component requiring the use of skeletal replacement (‘a’) nomenclature
186           P-24.5.3    Alphanumerical order
188           P-24.5.4    Ring systems modified by skeletal replacement (‘a’) nomenclature
188       P-24.6Unbranched Polyspiro Ring Systems with Different Components, One being a Polycyclic Ring System
189           P-24.6.1    If there is a choice of locants
190       P-24.7Branched Polyspiro Ring Systems
190           P-24.7.1    A central ring component is spirofused to three or more identical terminal ring components
191           P-24.7.2    Two or more different terminal ring components spirofused to a central component
192           P-24.7.3    If no decision can be attained by application of P-24.7.2
193           P-24.7.4    Additional components are spiro-fused to a branched polyspiro compound
195       P-24.8Spiro Ring Systems Containing Atoms with Nonstandard Bonding Numbers
195           P-24.8.1    Spiro ring systems with only monocyclic ring components
198           P-24.8.2    Monospiro ring systems with two identical polycyclic ring components
199           P-24.8.3    Spiro ring systems with three identical components and one nonstandard spiro atom
199           P-24.8.4    Monospiro ring systems with different ring components, at least one of which is a polycyclic ring with a nonstandard spiro atom
201           P-24.8.5    Unbranched polyspiro ring systems with different ring components, at least one of which is a polycyclic ring with at least one nonstandard spiro atom
202           P-24.8.6    Branched spiro ring systems with at least one polycyclic ring component
203   P-25Fused and Bridged Fused Ring Systems
204       P-25.0Introduction
205       P-25.1Names of Hydrocarbon Parent Ring Components
205           P-25.1.1    Retained names for hydrocarbons
207           P-25.1.2    Systematically named hydrocarbon parent components
208             P-        Polyacenes
208             P-        Polyaphenes
208             P-        Polyalenes
209             P-        Polyphenylenes
209             P-        Polynaphthylenes
210             P-        Polyhelicenes
210             P-        Ace...ylenes
211       P-25.2Names of Heterocyclic Parent Ring Components
211           P-25.2.1    Retained names for heterocycles
215           P-25.2.2    Systematically named heterocyclic components
215             P-        Heteromonocyclic parent components
216             P-        Heteranthrene components
216             P-        Pheno...ine components
217             P-        Heteromonocyclic components fused to a benzene ring
219       P-25.3Constructing Fusion Names
219           P-25.3.1    Definitions, terminology, and general principles
223           P-25.3.2    Constructing two-component fusion names
234           P-25.3.3    Numbering of fused ring systems
241           P-25.3.4    Constructing polycomponent fusion names
241             P-        Three types of fusion names
243             P-        Constructing polycomponent fusion names
243             P-          Order of seniority for selecting parent components
245             P-          Order of seniority for selecting attached components
247             P-          Order of citation of fusion prefixes
250             P-          Order of seniority of locants (letters and numbers)
253           P-25.3.5    Heteromonocyclics fused to a benzene ring
255           P-25.3.6    Identical attached components
257           P-25.3.7    Multiparent ring systems
261           P-25.3.8    Omission of locants in fusion descriptors
263       P-25.4Bridged Fused Ring Systems
263           P-25.4.1    Definitions and terminology
265           P-25.4.2    Names of bridges
265             P-        Bivalent bridges
269             P-        Polyvalent bridges
271             P-        Composite bridges
272           P-25.4.3    Naming bridged fused systems
281           P-25.4.4    Numbering bridge atoms
283           P-25.4.5    Order for numbering of bridges
284       P-25.5Limitations of Fusion Nomenclature: Three Components ortho and peri-fused Together
284           P-25.5.1    Skeletal replacement (‘a’) nomenclature
286           P-25.5.2    Selection of a less senior hydrocarbon parent component
287           P-25.5.3    Use of bridging nomenclature
287       P-25.6Fused Ring Systems with Skeletal Atoms with Nonstandard Bonding Numbers
289       P-25.7Double Bonds, Indicated Hydrogen, and the δ-Convention
289           P-25.7.1    Indicated hydrogen
293           P-25.7.2    The δ-convention
293       P-25.8Parent Components in Decreasing Order of Seniority (Partial Lists)
293           P-25.8.1    Partial list of heterocyclic parent components in decreasing order of seniority
297           P-25.8.2    Partial list of hydrocarbon parent components in decreasing order of seniority
298   P-26Phane Nomenclature
298       P-26.0Introduction
299       P-26.1Concepts and Terminology
299           P-26.1.1    Simplification and amplification
299           P-26.1.2    Simplified skeleton of the phane parent hydride, simplified phane parent graph, simplified skeletal name, and skeletal locants
300           P-26.1.3    Superatom and superatom locants
300           P-26.1.4    Amplificant, amplification prefix, and amplificant locants
300           P-26.1.5    Attachment atoms and attachment locants
300           P-26.1.6    Phane parent skeleton, phane parent name, and phane parent hydrides
300       P-26.2Components of Phane Parent Names
300           P-26.2.1    Simplified skeletal names
302           P-26.2.2    Amplification prefixes
303           P-26.2.3    Multiple identical amplificants
303       P-26.3Superatom Locants and Amplificant Attachment Locants
304           P-26.3.1    Superatom locants
304           P-26.3.2    Attachment locants
304       P-26.4Numbering of Phane Parent Hydride
304           P-26.4.1    Numbering of phane parent skeletons and amplificants
308           P-26.4.2    Numbering of simplified phane skeletons with respect to amplificant numbering
314           P-26.4.3    Numbering of phane parent hydrides
316       P-26.5Skeletal Replacement (‘a’) Nomenclature in Phane Nomenclature
316           P-26.5.1    Skeletal replacement (‘a’) nomenclature in simplified phane names
317           P-26.5.2    Skeletal replacement (‘a’) nomenclature in amplificants
318           P-26.5.3    Simultaneous skeletal replacement (‘a’) in simplified skeletal names and amplificants
318           P-26.5.4    Numbering of heterophane parent hydrides with respect to heteroatoms
322       P-26.6Other Aspects of Phane Nomenclature
322   P-27Fullerenes
322       P-27.0Introduction
323       P-27.1Definitions
323           P-27.1.1    Fullerenes
323           P-27.1.2    Fulleranes
323           P-27.1.3    Fulleroids
323       P-27.2Fullerene Names
323           P-27.2.1    Systematic names
324           P-27.2.2    Trivial names
324           P-27.2.3    Preferred IUPAC names
324       P-27.3Numbering of Fullerenes
327       P-27.4Structurally Modified Fullerenes
327           P-27.4.0    Introduction
327           P-27.4.1    Homofullerenes
328           P-27.4.2    Norfullerenes
329           P-27.4.3    Secofullerenes
330           P-27.4.4    Cyclofullerenes
330           P-27.4.5    Combination of structure-modifying operations
331       P-27.5Replacement of Skeletal Atoms
331           P-27.5.1    Fullerenes in which carbon atoms have been replaced by one or more heteroatoms
331           P-27.5.2    When ‘homo’, ‘nor’, ‘seco’, or ‘cyclo’ prefixes co-occur with skeletal replacement terms, such as ‘oxa’ or ‘aza’
332       P-27.6Addition of Rings and Ring Systems to Fullerenes
332           P-27.6.1    Fullerenes ortho fused to organic rings or ring systems
336           P-27.6.2    Bridged fullerenes
338           P-27.6.3    Spiro fullerenes
338       P-27.7Other Aspects of Fullerene Nomenclature
339   P-28Ring Assemblies
339       P-28.0Introduction
339       P-28.1Definitions
340       P-28.2Ring Assemblies of Two Identical Cyclic Systems
340           P-28.2.1    Ring assemblies with a single bond junction
341           P-28.2.2    Ring assemblies with a double bond junction
341           P-28.2.3    Indicated hydrogen of components in two-component ring assemblies
343       P-28.3Unbranched Ring Assemblies of Three through Six Identical Cyclic Systems
343           P-28.3.1    Unbranched ring assemblies consisting of three or more identical cyclic systems
344           P-28.3.2    Exceptions to the use of parent hydride names, ring assemblies of three through six benzene rings
345       P-28.4Ring Assemblies Composed of Identical Cyclic Systems Modified by Skeletal Replacement (‘a’) Nomenclature
345           P-28.4.1    Assemblies composed of identical heterocyclic compounds
346           P-28.4.2    Since hydrocarbon ring assemblies are the parent structures for the application of skeletal replacement (‘a’) nomenclature
347       P-28.5Ring Assembles Composed of More than Six Identical Cyclic Systems
347       P-28.6Branched Ring Assemblies of Identical Cyclic Systems
349       P-28.7Ring Assemblies of Nonidentical Cyclic Systems
349   P-29Prefixes Denoting Substituent Groups Derived from Parent Hydrides
350       P-29.0Introduction
350       P-29.1Definitions
350           P-29.1.1    A simple substituent group
350           P-29.1.2    A compound substituent group
351           P-29.1.3    A complex substituent group
352       P-29.2General Methodology for Naming Substituent Groups Prefixes
353       P-29.3Systematic Prefixes for Simple Substituents Groups Derived from Saturated Parent Hydrides
353           P-29.3.1    Substituent prefixes derived from mononuclear parent hydrides
354           P-29.3.2    Substituent prefixes derived from acyclic parent hydrides
357           P-29.3.3    Substituent prefixes derived from saturated cyclic parent hydrides
358           P-29.3.4    Substituent prefixes derived from mancude parent hydrides
360           P-29.3.5    Substituent prefixes derived from ring assemblies
361           P-29.3.6    Substituent prefixes derived from phane systems
362       P-29.4Compound Substituent Groups
362           P-29.4.1    Compound substituted substituent groups
364           P-29.4.2    Compound catenated substituent groups
364       P-29.5Complex Substituent Groups
364           P-29.5.1    Complex substituted substituent groups
365           P-29.5.2    Concatenated complex substituent groups
365       P-29.6Retained Names for Prefixes of Simple Substituent Groups Derived from the Parent Hydrides Described in Chapter P-2
366           P-29.6.1    Retained prefixes that are preferred prefixes
367           P-29.6.2    Retained prefixes that are not used as preferred prefixes
370           P-29.6.3    Retained prefixes no longer recommended as approved prefixes
372   P-30Introduction
372   P-31Modification of the Degree of Hydrogenation of Parent Hydrides
373       P-31.0Introduction
373       P-31.1Substituent Groups Derived from Parent Hydrides with ‘ene’ or ‘yne’ endings
373           P-31.1.1    General methodology
375           P-31.1.2    Acyclic parent hydrides
376           P-31.1.3    Monocyclic parent hydrides
379           P-31.1.4    Bi- and polycyclic von Baeyer parent hydrides
383           P-31.1.5    Spiro compounds monocyclic rings
386           P-31.1.6    Phane parent hydrides
388           P-31.1.7    Ring assemblies of unsaturated components
390       P-31.2Substituent Groups Modified by the Prefixes ‘hydro’ or ‘dehydro’
390           P-31.2.1    The prefixes ‘hydro/dehydro’
390           P-31.2.2    General methodology
391           P-31.2.3    The prefix ‘hydro’
391             P-        Modification of the degree of hydrogenation of monocyclic mancude compounds
392             P-        Names of saturated heteromonocyclic compounds
393             P-        Saturation of double bonds in polycyclic mancude compounds
393             P-            Retained names of partially saturated polycyclic mancude compounds
394             P-            Polycyclic mancude compounds
395             P-            Spiro compounds
395             P-            Phane compounds
396             P-            Ring assemblies
399           P-31.2.4    The prefix ‘dehydro’
400   P-32Prefixes for Substituent Groups Derived from Parent Hydrides with a Modified Degree of Hydrogenation
400       P-32.0Introduction
400       P-32.1Substituent Groups Derived from Parent Hydrides with ‘ene’ or ‘yne’ endings
400           P-32.1.1    Substituents derived from unsaturated acyclic compounds
402           P-32.1.2    Monocyclic substituent groups
402           P-32.1.3    Substituent groups derived from parent hydrides having a fixed numbering
403       P-32.2Substituent Groups Modified by the Prefix ‘hydro’
403           P-32.2.1    For heteromonocyclic parent hydrides
403           P-32.2.2    For polycyclic mancude compounds
404           P-32.2.3    With added indicated hydrogen
405       P-32.3Retained Names for Substituent Groups Derived from Unsaturated Acyclic Parent Hydrides
407       P-32.4Retained Names for Substituent Groups Derived from Partially Saturated Polycyclic Parent Hydrides
407   P-33Suffixes
407       P-33.0Introduction
407       P-33.1Definitions
408       P-33.2Functional Suffixes
408           P-33.2.1    Basic functional suffixes
409           P-33.2.2    Derived preferred and preselected suffixes
412       P-33.3Cumulative Suffixes
413   P-34Functional Parent Compounds
413       P-34.0Introduction
414       P-34.1Retained Functional Parent Compounds
414           P-34.1.1    Organic functional parent compounds (arranged by characteristic group class)
416           P-34.1.2    Organic functional parent compounds (arranged alphabetically)
417           P-34.1.3    Organic functional parent compounds for general and specialized nomenclature
417           P-34.1.4    Inorganic functional parent compouinds
418       P-34.2Substituent Groups Related to Functional Parent Compounds
418           P-34.2.1    Organic substituent groups (arranged by classes)
420           P-34.2.2    Organic substituent groups (arranged alphabetically)
421           P-34.2.3    Substituent group names derived from organic compounds used in general and specialized nomenclature
421           P-34.2.4    Preselected substituent group names
421   P-35Prefixes Corresponding to Characteristic Groups
421       P-35.0Introduction
422       P-35.1General Methodology
422       P-35.2Simple Prefixes Denoting Characteristic Groups
422           P-35.2.1    Retained traditional prefixes
423           P-35.2.2    Substituents formed by subtracting one or more hydrogen atoms from mono and dinuclear parent hydrides
425           P-35.2.3    Simple prefixes derived from functional parent compounds
425       P-35.3Compound Substituent Prefixes
425           P-35.3.1    Names of compound prefixes derived from suffixes or functional parent compounds by substitution
426           P-35.3.2    Names of compound prefixes derived from suffixes or functional parent compounds by concatenation
426       P-35.4Complex Substituent Prefixes
426           P-35.4.1    Complex substituent prefixes by substitution
427           P-35.4.2    Complex substituent prefixes by concatenation
427       P-35.5Mixed Substituent Prefixes
427           P-35.5.1    Mixed substituent prefixes names using substitutive and additive operations
428   P-40Introduction
428   P-41Seniority Order for Classes
431   P-42Seniority Order for Acids
432       P-42.1Class 7a. Acids Expressed by Suffixes (Excludes Carbonic and Polycarbonic acids)
432       P-42.2Class 7b. Carbon Acids with no Substitutable Hydrogen Atoms
432       P-42.3Class 7c. Noncarbon Acids having Substitutable Hydrogen Atoms on the Central Atom
433       P-42.4Class 7d. Noncarbon Acids used to Generate Derivatives having Substitutable Hydrogen Atoms
435       P-42.5Class 7e. Other Monobasic ‘oxo’ Acids used as Functional Parents
436   P-43Seniority Order for Suffixes
436       P-43.0Introduction
436       P-43.1General Methodology of Functional Replacement
446   P-44Seniority order for parent structures
447       P-44.0Introduction
447       P-44.1Seniority Order for Parent Structures
447           P-44.1.1    Maximum number of substituents corresponding to the principal characteristic group
449           P-44.1.2    Senior atom in accordance with the seniority of classes
452           P-44.1.3    Seniority order only for rings and ring systems
453           P-44.1.4    Seniority among acyclic chains (the principal chain)
453           P-44.1.5    Other criteria
453       P-44.2Seniority Order only for Rings and Ring Systems
453           P-44.2.1    General criteria (other than phanes)
453             P-        General methodology
455             P-        A heterocycle
455             P-        At least one nitrogen ring atom
456             P-        At least one heteroatom (in the absence of nitrogen) that occurs earlier from a list
456             P-        The greater number of rings
457             P-        Greater number of skeletal atoms
457             P-        Greater number of heteroatoms of any kind
458             P-        Greater number of heteroatoms that occur earlier from a list
460           P-44.2.2    Criteria specific to a particular kind of ring or ring system
460             P-        Monocycles
460             P-        Polycyclic systems
461             P-            Spiro ring systems
464             P-            Cyclic phane systems
469             P-            Fused ring systems
471             P-            Bridged fused ring systems
477             P-            Von Baeyer ring systems
479             P-            Linear (acyclic) phanes
487             P-            Ring assemblies
490       P-44.3Seniority of Acyclic Chains (the Principal Chain)
490           P-44.3.1    Greater number of acyclic heteroatoms of any kind
491           P-44.3.2    Greater number of skeletal atoms
493           P-44.3.3    Greater number of the most senior acyclic heteroatom
493       P-44.4Seniority Criteria Applicable to Rings, Ring Systems, or Acyclic Chains
493           P-44.4.1    If P-44.1 through P-44.3, does not effect a choice of senior parent structure
494             P-        Greater number of multiple bonds
495             P-        Greater number of double bonds
497             P-        One or more atoms with nonstandard bonding numbers
499             P-        Lowest locants for indicated hydrogen
499             P-        Lower locants for heteroatoms introduced by skeletal replacement (‘a’) nomenclature as a set
501             P-        Lower locants for heteroatoms introduced by skeletal replacement (‘a’) nomenclature in the order
503             P-        Lower locant(s) for carbon atoms at fusion sites
503             P-        Lower locants for characteristic groups cited as a suffix
505             P-        Lowest locants for points of attachment (if a substituent group)
505             P-        Lowest locants for endings or prefixes that express changes in the degree of hydrogenation,
       i.e., for ‘ene’ and ‘yne’ endings and ‘hydro/dehydro’ prefixes
509             P-        One or more isotopically modified atoms
511             P-        One or more stereogenic centers
515   P-45Selection of the Preferred IUPAC Name
515       P-45.0Introduction
515       P-45.1Multiplication of Identical Senior Parent Structures
515           P-45.1.1    Multiplicative nomenclature is senior to substitutive nomenclature
516           P-45.1.2    Choice between two or more parent structures
517       P-45.2Criteria Related to Number and Location of Substituent Groups
517           P-45.2.1    Maximum number of substituent groups cited as prefixes
521           P-45.2.2    Lower locant set for substituent groups cited as prefixes
526           P-45.2.3    Lower locant set for substituent groups in order of citation in the name
528       P-45.3Criteria Related only to Substituents with Nonstandard Bonding Numbers, other Criteria being Equal
528           P-45.3.1    Maximum number of substituent group(s) with the higher bonding number cited as prefixes
529           P-45.3.2    Lower locant set for substituent group(s) with the higher bonding number cited as prefixes
529       P-45.4Criteria Related only to Isotopic Modification, other Criteria being Equal
529           P-45.4.1    Senior parent structure that has the greater number of isotopically modified substituent groups
530           P-45.4.2    Senior parent structure that has the greater number of nuclides of higher atomic number
530           P-45.4.3    Senior parent structure that has the greater number of nuclides of higher mass number
530           P-45.4.4    Senior parent structure that has the lowest locant(s) for isotopically modified substituent groups
531           P-45.4.5    Senior parent structure that has the lowest locant(s) for nuclides of higher atomic number
531           P-45.4.6    Senior parent structure that has the lowest locant(s) for nuclides of higher mass number
531       P-45.5Criteria Related to Alphanumerical Order of Names
531           P-45.5.1    Earlier in alphanumerical order
535           P-45.5.2    When names based on alphanumerical order are the same
536       P-45.6Criteria Related only to Configuration
536           P-45.6.1    Introduction
536           P-45.6.2    General principles
538           P-45.6.3    Alphabetic order of the stereochemical descriptors ‘R’ and ‘S
539           P-45.6.4    Application of CIP sequence rules 4 and 5
540   P-46The Principal Chain in Substituent Groups
540       P-46.0Introduction
541       P-46.1The Principal Substituent Chain
542           P-46.1.1    Greater number of heteroatoms
542           P-46.1.2    Greater number of skeletal atoms
542           P-46.1.3    Greater number of heteroatoms in a set order
543           P-46.1.4    Greater number of multiple bonds, then double bonds
543           P-46.1.5    One or more atoms with nonstandard bonding numbers
544           P-46.1.6    Lowest locants for heteroatoms
545           P-46.1.7    Lowest locants for heteroatoms appearing first a set order
545           P-46.1.8    Lowest locants for free valences of any kind in the order ‘yl’ > ‘ylidene’ > ‘ylidyne’
546           P-46.1.9    Lowest locant(s) for multiple bonds, then double bonds
546           P-46.1.10    Lowest locant(s) for (an) atom(s) with nonstandard bonding number(s)
547           P-46.1.11    Greatest number of substituents of any kind
548           P-46.1.12    Lowest locants for substituents
549           P-46.1.13    Lowest locants for the substituent(s) cited earlier in alphanumerical order
549       P-46.2Principal Substituent Chains in Isotopically Labeled Compounds
549           P-46.2.1    Greater number of isotopically modified atoms
550           P-46.2.2    Greater number of nuclides of higher mass number or isotopically modified substituent atoms or groups
550       P-46.3Principal Substituent Chains in Compounds with Stereogenic Centers
550           P-46.3.1    Greater number of (Z)-double bonds
551           P-46.3.2    Greater number of (R)-chiral centers
552   P-50Introduction
553   P-51Selecting the Preferred Type of IUPAC Nomenclature
553       P-51.0Introduction
553       P-51.1Selecting the Preferred Type of Nomenclature
553           P-51.1.1    Substitutive nomenclature is preferred to functional class nomenclature
554           P-51.1.2    Substitutive nomenclature is preferred to conjunctive nomenclature
554           P-51.1.3    Skeletal replacement (‘a’) nomenclature is preferred to substitutive nomenclature
554           P-51.1.4    Skeletal replacement (‘a’) nomenclature is preferred to multiplicative nomenclature
554           P-51.1.5    Multiplicative nomenclature is preferred to simple substitutive nomenclature
555       P-51.2Functional Class Nomenclature
555           P-51.2.1    Characteristic groups with preferred IUPAC names using functional class nomenclature
556           P-51.2.2    Functional class nomenclature for general nomenclature
557       P-51.3Multiplicative Nomenclature
557           P-51.3.1    Preferred IUPAC multiplicative names
559           P-51.3.2    When more than two identical parent structures occur in the structure
563           P-51.3.3    When conditions (1), (2), and (3) as defined in P-53.3.1 are not met
563       P-51.4Skeletal Replacement (‘a’) Nomenclature
564           P-51.4.1    Skeletal replacement (‘a’) nomenclature in acyclic chains
567           P-51.4.2    Skeletal replacement (‘a’) nomenclature for cyclic compounds
570       P-51.5 Conjunctive Nomenclature vs. Substitutive Nomenclature
571   P-52Selecting Preferred IUPAC Names and Preselected Names for Parent Hydrides
572       P-52.1Selecting Preselected Names
572           P-52.1.1    Mononuclear parent hydride names
572           P-52.1.2    Preselected names for homogeneous acyclic polynuclear parent hydrides
572           P-52.1.3    Preselected names for heterogeneous acyclic parent hydrides
572           P-52.1.4    Preselected names for parent hydrides with nonstandard bonding numbers
573           P-52.1.5    Heteromonocyclic noncarbon Hantzsch-Widman parent hydrides
574           P-52.1.6    Heterocyclic noncarbon von Baeyer and spiro compounds
575           P-52.1.7    Preselected names for homogeneous and heterogeneous heterobi- and heteropolycyclic fused ring systems
576       P-52.2Selecting Preferred IUPAC Names
576           P-52.2.1    Acyclic and monocyclic hydrocarbons
577           P-52.2.2    Heteroacyclic and heteromonocycles
577           P-52.2.3    Unsaturated heteromonocyclic compounds with more than ten ring members
578           P-52.2.4    Preferred IUPAC names in fusion nomenclature
578             P-        Five-membered ring requirement
578             P-        Heteromonocycles as components in fusion names
579             P-        Multiparent fused ring systems with three or more interparent components
580             P-        Limitations to fusion nomenclature
584           P-52.2.5    Preferred IUPAC names in phane nomenclature
588           P-52.2.6    Preferred IUPAC names for (C60-Ih)[5,6]fullerene and (C70-D5h(6))[5,6]fullerene with ‘nor’ or ‘seco’ prefixes
594           P-52.2.7    Preferred IUPAC names and numbering for ring assemblies
596           P-52.2.8    Selection between a ring and a chain as parent hydride
596   P-53Selecting Preferred Retained Names of Parent Hydrides
597   P-54Selecting the Preferred Method for Modifying the Degree of Hydrogenation
597       P-54.1Methods for Modifying the Degree of Hydrogenation of Parent Hydrides:
597       P-54.2Unsaturated Monocyclic Carbocycles
598       P-54.3Unsaturation in Ring Assemblies Composed of Mancude and Saturated Rings
598       P-54.4Names Modified by ‘hydro’ or ‘dehydro’ Prefixes
598           P-54.4.1    Hantzsch-Widman heteromonocycles
599           P-54.4.2    Saturated heteromonocyclic compounds
600           P-54.4.3    Fused ring systems and monocyclic mancude ring assemblies
602           P-54.4.4    Names modified by ‘dehydro’ prefixes
603   P-55Selecting the Preferred Retained Name for Functional Parent Compounds
603   P-56Selecting the Preferred Suffix for the Principal Characteristic Group
603       P-56.1The Suffix ‘peroxol’ for -OOH
604       P-56.2The Suffixes ‘SO-thioperoxol’, and Chalogen Analogues
604       P-56.3The Suffixes ‘imidamide’ and ‘carboximidamide’
604       P-56.4The Endings ‘diyl’ and ‘ylidene’ vs. ‘ylene’
606   P-57Selecting Prefered and Preselected Prefixes for Substituent Groups
606       P-57.1Substituent Prefixes Derived from Parent Hydrides
606           P-57.1.1    Prefixes derived from mononuclear and acyclic parent hydrides
607           P-57.1.2    Retained names used as preferred prefixes
607           P-57.1.3    Retained prefixes recommended only for general nomenclature
607           P-57.1.4    Retained prefixes no longer recommended
607           P-57.1.5    Prefixes derived from cyclic parent hydrides
609           P-57.1.6    Prefixes derived from parent hydrides with modified degrees of hydrogenation
612       P-57.2Prefixes Derived from Characteristic (functional) Groups
612       P-57.3Prefixes Derived from Organic Functional Parent Compounds
612       P-57.4Construction of Linear Compound and/or Complex Substituent Prefixes.
614   P-58Selecting Preferred IUPAC Names
614       P-58.1Introduction
615       P-58.2Indicated Hydrogen, ‘Added Indicated Hydrogen’, and Nondetachable Hydro Prefixes
615           P-58.2.1    Indicated hydrogen
617           P-58.2.2    ‘Added indicated hydrogen’
620           P-58.2.3    Specific rules related to indicated hydrogen, ‘added indicated hydrogen’ and hydro prefixes
625           P-58.2.4    Prefix nomenclature
625           P-58.2.5    Nondetachable hydro prefixes vs. indicated hydrogen
627       P-58.3Homogeneous Hetero Chains and Functional Groups
627           P-58.3.1    Preselected names for unbranched homogeneous heteroacyclic parent hydrides
627           P-58.3.2    Atoms expressed by a principal characteristic group, a functional parent compound, or a compulsory prefix
628   P-59Name Construction
628       P-59.0Introduction
628       P-59.1General Methodology
628           P-59.1.1    Determine the type(s) of nomenclature and operations to be used
628           P-59.1.2    Determine the type(s) of nomenclature and operations to be used
629           P-59.1.3    Select the parent hydride(s)
629           P-59.1.4    Name the parent hydride, and the principal characteristic group
629           P-59.1.5    Determine affixes and/or prefixes
629           P-59.1.6    Name substituent groups and characteristic groups not cited as principal characteristic groups as prefixes
629           P-59.1.7    Assemble the components into a complete name
629           P-59.1.8    Complete the name with all required descriptors for stereochemical features
629           P-59.1.9    Characteristic groups
631           P-59.1.10    Numbering nomenclatural features
632       P-59.2Examples Illustrating the General Methodology
632           P-59.2.1    Selection of parent hydrides
639           P-59.2.2    Seniority of heteroatoms over principal characteristic groups
641           P-59.2.3    Seniority of principal characteristic groups over unsaturation
646           P-59.2.4    Seniority of hydro/dehydro prefixes over detachable prefixes
646           P-59.2.5    Treatment of detachable prefixes
648   P-60Introduction
648       P-60.1Topical Outline
648       P-60.2Presentation of Names
649   P-61Substitutive Nomenclature: Prefix Mode
649       P-61.0Introduction
650       P-61.1General Methodology
651       P-61.2Hydrocarbyl Groups and Corresponding Di- and Polyvalent Groups
652           P-61.2.1    Acyclic hydrocarbons
652           P-61.2.2    Cyclic hydrocarbons
653           P-61.2.3    Hydrocarbons consisting of rings and chains
656           P-61.2.4    Structures containing heterocycles
656       P-61.3Halogen Compounds
656           P-61.3.1    Halogen atoms in its standard bonding number
660           P-61.3.2    Halogen atoms attached to heteroatoms
661           P-61.3.3    Compounds containing the group –I(OH)2 or similar groups
661           P-61.3.4    Retained names
661       P-61.4Diazo Compounds
662       P-61.5Nitro and Nitroso Compounds
662           P-61.5.1    Nitro and nitroso compounds
663           P-61.5.2    Nitro attached to heteroatoms
663           P-61.5.3    aci-Nitro compounds
663       P-61.6Heterones
664       P-61.7Azides
664       P-61.8Isocyanates
665       P-61.9Isocyanides
666       P-61.10Fulminates and Isofulminates
666       P-61.11Polyfunctional Compounds
667           P-61.11.1    Low locants assigned as a set
667           P-61.11.2    Low locants assigned to the prefix cited first in the name
667   P-62Amines and Imines
667       P-62.0Introduction
668       P-62.1General Methodology
668       P-62.2Amines
668           P-62.2.1    Primary amines
671           P-62.2.2    Secondary and tertiary amines
674           P-62.2.3    The prefix ‘amino’
675           P-62.2.4    Polyamines
679           P-62.2.5    Multiplicative nomenclature
681           P-62.2.6    Modification of the degree of saturation/unsaturation of amines
682       P-62.3Imines
682           P-62.3.1    Substitutive names for imines
685       P-62.4N-Substitution of Amines and Imines by Heteroatoms
685       P-62.5Amine Oxides, Imine Oxides, and Chalcogen Analogues
687       P-62.6Amine and Imine Salts
687           P-62.6.1    Cation and anion names
688           P-62.6.2    Salts of indefinite structure (adducts)
689   P-63Hydroxy Compounds, Ethers, Peroxols, Peroxides, and Chalcogen Analogues
689       P-63.0Introduction
690       P-63.1Hydroxy Compounds and Chalcogen Analogues
690           P-63.1.1    Retained names
692           P-63.1.2    Systematic names of alcohols, phenols, enols, and ynols
696           P-63.1.3    Heterols
696           P-63.1.4    Substitutive nomenclature, prefix mode
697           P-63.1.5    Sulfur, selenium and tellurium analogues of hydroxy compounds
699       P-63.2Ethers and Chalcogen Analogues
699           P-63.2.1    Definitions and general methodology
700           P-63.2.2    Names of substituent groups R′-O–, R′-S–, R′-Se–, and R′-Te–
702           P-63.2.3    Retained names
703           P-63.2.4    Systematic names of ethers
705           P-63.2.5    Chalcogen analogues of ethers: sulfides, selenides, and tellurides
707       P-63.3Peroxides and Chalcogen Analogues
707           P-63.3.1    Peroxides, disulfides, diselenides, and ditellurides
709           P-63.3.2    Mixed chalcogen analogues of peroxides
711       P-63.4Hydroperoxides (Peroxols) and Chalcogen Analogues
711           P-63.4.1    Hydroperoxides
712           P-63.4.2    Chalcogen analogues of hydroperoxides
713       P-63.5Cyclic Ethers, Sulfides, Selenides, and Tellurides
715       P-63.6Sulfoxides and Sulfones
716       P-63.7Polyfunctional Compounds
719       P-63.8Salts of Hydroxy Compounds, Hydroperoxy Compounds and Their Chalcogen Analogues
719           P-63.8.1    Neutral salts of hydroxy compounds and their chalcogen analogues
719           P-63.8.2    Cyclic salts are named as heterocycles
720           P-63.8.3    Partial salts of polyols and their chalcogen
720   P-64Ketones, Pseudoketones, Heterones, and Chalcogen Analogues
720       P-64.0Introduction
720       P-64.1Definitions
720           P-64.1.1    Ketones
721           P-64.1.2    Pseudoketones and heterones
722       P-64.2Ketones
722           P-64.2.1    Retained names
725           P-64.2.2    Systematic construction of names for ketones
725             P-        Acyclic ketones
727             P-        Cyclic ketones
729             P-        Seniority order for numbering
732             P-        Ketenes
732       P-64.3Pseudoketones
732           P-64.3.1    Cyclic anhydrides, esters and amides
734           P-64.3.2    Acyclic pseudoketones
734       P-64.4Heterones
735           P-64.4.1    Acyclic heterones
735           P-64.4.2    Thioketone and thioaldehyde oxides
736       P-64.5Carbonyl Groups as Prefixes
736           P-64.5.1    Ketones
738           P-64.5.2    Pseudoketones
739       P-64.6Chalcogen Analogues of Ketones, Pseudoketones, and Heterones
739           P-64.6.1    Chalcogen analogues of ketones, pseudoketones and heterones
740           P-64.6.2    Seniority order of suffixes
741       P-64.7Polyfunctional Ketones, Pseudoketones and Heterones
741           P-64.7.1    Ketones, pseudoketones and heterones, and their chalcogen analogues
743           P-64.7.2    There is no seniority order difference between ketones and pseudoketones
743           P-64.7.3    When an oxygen atom of a ketone, pseudoketone, or heterone is replaced by a sulfur, selenium or tellurium atom
743       P-64.8Acyloins
744   P-65Acids, Acyl Halides and Pseudohalides, Salts, Esters, and Anhydrides
744       P-65.0Introduction
745       P-65.1Carboxylic Acids and Functional Replacement Analogues
745           P-65.1.1    Retained names
749           P-65.1.2    Systematic names
749             P-        Carboxylic acid groups
750             P-        The suffix ‘carboxylic acid’
752             P-        Seniority order for numbering
753             P-        Polyfunctional carboxylic acids
755           P-65.1.3    Carboximidic, carbohydrazonic, carbohydroximic, and carbohydroxamic acids
755             P-        Carboximidic acids
757             P-        Carbohydrazonic acids
759             P-        Carbohydroximic acids
761           P-65.1.4    Peroxycarboxylic acids
762           P-65.1.5    Chalcogen analogues of carboxylic acids
762             P-        Functional replacement in systematic names of carboxylic acids
764             P-        Functional replacement in retained names of carboxylic acids
766             P-        Functional replacement in peroxycarboxylic acids
767           P-65.1.6    Amic, anilic, and aldehydic acids
769           P-65.1.7    Acyl groups derived from carboxylic and related acids
769             P-        Definitions and name formation
769             P-        Carboxylic acids having retained names that are preferred IUPAC names
772             P-        Carboxylic acids with names retained only for general nomenclature
774             P-        Systematically named carboxylic acids
776             P-        Mixed acyl groups
776           P-65.1.8    Formic acid
777       P-65.2Carbonic, Cyanic, and Di- and Polycarbonic Acids
778           P-65.2.1    Carbonic acid
784           P-65.2.2    Cyanic acid
785           P-65.2.3    Di-, tri-, tetra-, and polycarbonic acids
788       P-65.3Sulfur, Selenium, Tellurium Acids with Chalcogen Atoms Directly Linked to a Parent Hydride
788           P-65.3.0    Introduction
789           P-65.3.1    Substitutive nomenclature, suffix mode, for sulfonic, sulfinic, etc., acid
791           P-65.3.2    Substitutive nomenclature, prefix mode for sulfonic, sulfinic, etc. acids
794           P-65.3.3    Polyfunctional compounds
795       P-65.4Acyl Groups as Substituent Groups
795           P-65.4.1    General methodology
796       P-65.5Acid Halides and Pseudohalides
796           P-65.5.1    Acyl halides from suffix acids
798           P-65.5.2    Acyl pseudohalides from suffix acids
798           P-65.5.3    Acyl halides and pseudohalides from carbonic, cyanic, and the polycarbonic acids
799           P-65.5.4    Acyl halides and pseudo halides as substituent groups
801       P-65.6Salts and Esters
801           P-65.6.1    General methodology
801           P-65.6.2    Salts
803           P-65.6.3    Esters, lactones, and related compounds
803             P-        Definitions
804             P-        General methodology
807             P-        Peferred IUPAC names for esters
807             P-            Monoesters
807             P-            Polyesters derived from a single acid component
810             P-            Polyesters formed from a single ‘alcoholic’ component
811             P-            Polyesters derived from multiple acid components and multiple ‘alcoholic’ components
816             P-            Partial esters from polybasic acids and salts
818             P-            Substitutive nomenclature is senior to functional class nomenclature for preferred IUPAC names for esters
818             P-            Esters of acids modified by functional replacement
821             P-        Pseudoesters
822             P-        Cyclic esters
826             P-        Acylals
826       P-65.7Anhydrides and Their Analogues
826           P-65.7.0    Introduction
826           P-65.7.1    Symmetric anhydrides
827           P-65.7.2    Mixed anhydrides
828           P-65.7.3    Thioanhydrides and other chalcogen analogues
829           P-65.7.4    Peroxyanhydrides and chalcogen analogues
829           P-65.7.5    Diacyl derivatives of trioxidane and chalcogen analogues
830           P-65.7.6    Di- and polyanhydrides
834           P-65.7.7    Cyclic anhydrides
838           P-65.7.8    Polyfunctional anhydrides
839   P-66Amides, Imides, Hydrazides, Nitriles, Aldehydes, their Chalcogen Analogues and Derivatives
839       P-66.0Introduction
839       P-66.1Amides
840           P-66.1.0    Introduction
840           P-66.1.1    Primary amides
840             P-        Carboxamides
842             P-        Sulfonamides, sulfinamides, and related selenium and tellurium amides
843             P-        Substitution of primary amides
847             P-        Amides denoted as prefixes
854           P-66.1.2    Secondary and tertiary amides
855           P-66.1.3    ‘Hidden’ amides
856           P-66.1.4    Chalcogen analogues of amides
858           P-66.1.5    Lactams, lactims, sultams, and sultims
860           P-66.1.6    Amides derived from carbonic, cyanic, and the di- and polycarbonic acids
860             P-        Carbonic acid and related compounds
867             P-        Cyanic acid
867             P-        Di- and polycarbonic acids
868           P-66.1.7    Polyfunctional amides
868       P-66.2Imides
868           P-66.2.1    Acyclic imides and cyclic imides
869           P-66.2.2    Imide prefixes
870       P-66.3Hydrazides
870           P-66.3.0    Definition
870           P-66.3.1    Systematic names
874           P-66.3.2    Substituent groups derived from hydrazides
876           P-66.3.3    Substituted hydrazides
878           P-66.3.4    Chalogen analogues of hydrazides
878           P-66.3.5    Hydrazides from carbonic, cyanic, and di- and polycarbonic acids
880           P-66.3.6    Semioxamazones
880       P-66.4Amidines, Amidrazones, Hydrazidines, and Amidoximes (Amide Oximes)
880           P-66.4.1    Amidines
880             P-        Suffixes for amidines
883             P-        Amidines of carbonic, and di- and the polycarbonic acids
885             P-        Prefixes for the amidine characteristic group
887             P-        Substituted amidines
889             P-        Formamidine disulfides
890             P-        Diamidides
890           P-66.4.2    Amidrazones
890             P-        Amidrazone suffixes
892             P-        Amidrazones of carbonic acid and di- and polycarbonic acids
893             P-        Amidrazone prefixes
895           P-66.4.3    Hydrazidines
895             P-        Hydrazidine suffixes
897             P-        Hydrazidines derived from sulfonic acid, and similar selenium and tellurium acids
898             P-        Hydrazidines derived from carbonic acid and di- and polycarbonic acids
898             P-        Hydrazidine prefixes
899           P-66.4.4    Amidoximes (amide oximes)
899       P-66.5Nitriles
900           P-66.5.0    Introduction
900           P-66.5.1    Preferred names for nitriles
904           P-66.5.2    Substituted nitriles
905           P-66.5.3    Nitriles/cyanides corresponding to carbonic and di- and the polycarbonic acids
905           P-66.5.4    Nitrile oxides and chalcogen analogues
906       P-66.6Aldehydes
906           P-66.6.0    Definition
906           P-66.6.1    Systematic names of aldehydes
909           P-66.6.2    Aldehydes from oxalic acid and polycarbonic acids
910           P-66.6.3    Chalcogen analogues of aldehydes
910           P-66.6.4    Polyfunctional aldehydes
911           P-66.6.5    Acetals and ketals, hemiacetals and hemiketals, and their chalcogen analogues
915   P-67Mononuclear and Polynuclear Noncarbon Acids and their Functional Replacement Analogues as Functional Parents for Naming Organic Compounds
915       P-67.0Introduction
915       P-67.1Mononuclear Noncarbon Oxoacids
916           P-67.1.1    Names for mononuclear noncarbon oxoacids and their derivatives formed by substitution
919           P-67.1.2    Functional replacement nomenclature applied to noncarbon oxoacids
919             P-        Mononuclear acids modified by infixes
920             P-        Mononuclear acids modified by prefixes
921             P-        General methodology for functional replacement nomenclature
923             P-        Acids modified by functional replacement nomenclature
926             P-        Acid halides and pseudohalides
927             P-        Amides and hydrazides
930           P-67.1.3    Esters and anhydrides of noncarbon oxoacids
934           P-67.1.4    Substituent groups derived from noncarbon oxoacids expressed as prefixes
934             P-        Mononuclear nitrogen, phosphorus, arsenic, and antimony acids
934             P-            Preselected prefixes
941             P-            Substituent groups for general nomenclature
941             P-            Compound and complex substituent groups
941             P-        Boric acid and silicic acid
942             P-        Nitric and nitrous acids
943             P-        Sulfur, selenium and tellurium acids
946             P-        Halogen acids
946           P-67.1.5    Seniority order among noncarbon oxoacids and derivatives
947           P-67.1.6    aci-Nitro compounds
948       P-67.2Di- and Polynuclear Noncarbon Oxoacids
949           P-67.2.1    Preselected names
951           P-67.2.2    Functional replacement nomenclature
954           P-67.2.3    Acid halides and pseudohalides
955           P-67.2.4    Amides and hydrazides
958           P-67.2.5    Esters and anhydrides
960           P-67.2.6    Substituent groups cited as prefixes
961       P-67.3Substitutive Names and Functional Class Names of Polyacids
961           P-67.3.1    Polynuclear noncarbon oxoacids that cannot be formed on the basis of fundamental oxoacids
963           P-67.3.2    The disulfurous acid name dilemma
964   P-68Nomenclature of Organic Compounds of the Group 13, 14, 15, 16, and 17 Elements not Included in Sections P-62 through P-67
964       P-68.0Introduction
965       P-68.1Nomenclature of Compounds of Group 13 Elements
965           P-68.1.1    Parent hydrides
969           P-68.1.2    Names for substituent groups derived from parent hydrides
971           P-68.1.3    Modification of the degree of hydrogenation
971           P-68.1.4    Functional parent compounds
973           P-68.1.5    Substitutive nomenclature
973             P-        Suffix nomenclature
974             P-        Prefix nomenclature
978           P-68.1.6    Adducts
979             P-        Structures for Lewis ‘adducts’
984       P-68.2Nomenclature of Compounds of Group 14 Elements
984           P-68.2.0    Introducction
985           P-68.2.1    Silicon, germanium, tin, and lead parent hydrides
986           P-68.2.2    Substituent groups derived from parent hydrides
988           P-68.2.3    Modification of the degree of hydrogenation
988           P-68.2.4    Silicic acid as a functional parent compound
989           P-68.2.5    Substitutive nomenclature: suffix mode
990           P-68.2.6    Substitutive nomenclature: prefix mode
992       P-68.3Nomenclature of Compounds of Group 15 Elements
993           P-68.3.1    Nitrogen compounds
993             P-        Introduction
993             P-        Hydroxylamines, oximes, and nitrolic acids and nitrosolic acids
998             P-        Hydrazine and related compounds
1004             P-        Diazene and related compounds
1005             P-            Substitution of diazene
1005             P-            Azo compounds, R-N=N-R′
1009             P-            Azoxy compounds, R-N=N(O)-R′
1011             P-            Diazenecarbohydrazide, HN=N-CO-NH-NH2
1011             P-            Formazan, H2N-N=CH-N=NH
1014             P-            Carbodiazone [bis(diazenyl)methanone], HN=N-CO-N=NH
1015             P-            Isodiazene, R2N+=N
1015             P-        Polyazanes
1016           P-68.3.2    Phosphorus, arsenic, and antimony compounds
1016             P-        General methodology
1017             P-        Parent hydrides
1018             P-        Substitutive nomenclature
1022           P-68.3.3    Bismuth compounds
1024       P-68.4Nomenclature of Compounds of Group 16 Elements
1024           P-68.4.0    Introduction
1024           P-68.4.1    Three or more homogeneous contiguous chalcogen atoms
1026           P-68.4.2    Three or more heterogeneous contiguous chalcogen atoms
1029           P-68.4.3    Chalcogen parent hydrides with nonstandard bonding numbers
1030             P-        Sulfanes, selanes, and tellanes
1030             P-        Di- and polysulfoxides, polysulfones, and selenium and tellurium analogues
1031             P-        Sulfimides, and chalcogen analogues, H2E=NH, where E = S, Se, or Te
1031             P-        Sulfinylamines, RN=E=O, sulfonylamines, RN=E(=O)2 and chalcogen analogues where E = S, Se, or Te
1032             P-        Sulfonediimines, RE(=NH)2R′ and chalcogen compounds where E = S, Se, or Te
1032             P-        Sulfoximides, R2E(=O)=NR′ and chalcogen analogues where E = S, Se, or Te
1032             P-        Sulfur dimides, HN=E=NH and chalcogen analogues where E = S, Se, or Te)
1033             P-        Sulfur triimides, E(=NH)3 and chalcogen analogues where E = S, Se, or Te)
1033       P-68.5Nomenclature of Compounds of Group 17 Elements
1033           P-68.5.0    Substitutive nomenclature
1033           P-68.5.1    Nomenclature based on halogen parent hydrides
1034           P-68.5.2    Nomenclature of halogen acids
1034           P-68.5.3    Amides if halogen acids
1035   P-69Nomenclature of Organometallic Compounds
1035       P-69.0Introduction
1036       P-69.1Organometallic Compounds of Elements in Groups 13, 14, 15, and 16
1036       P-69.2Organometallic Compounds of Elements in Groups 3 through 12
1036           P-69.2.1    Coordination nomenclature
1036           P-69.2.2    Definitions of terms
1038           P-69.2.3    Compounds with at least one metal-carbon single bond
1038           P-69.2.4    Organometallic groups with multicenter bonding to carbon atoms
1040           P-69.2.5    Bridging organometallic groups with multicenter bonding to carbon atoms
1040           P-69.2.6    Organometallic compounds with unsaturated molecules and substituent groups
1041           P-69.2.7    ‘‘Ocenes’’
1043       P-69.3Organometallic Compounds of Elements in Groups 1 and 2
1044       P-69.4Metallacycles
1046       P-69.5Order of Seniority Order for Organometallic Compounds
1046           P-69.5.1    Compounds having two identical or different metal atoms
1046           P-69.5.2    Compounds having one metal atom of class (1) and another atom of class (2)
1047           P-69.5.3    For organometallic compounds having two metal atoms belonging to class (2)
1048   P-70Introduction
1048       P-70.1General Methodology
1048       P-70.2Seniority of Radicals and Ions
1048       P-70.3Name Formation
1048           P-70.3.1    Suffixes, prefixes, and endings for radicals and ions in substitutive nomenclature
1049           P-70.3.2    Basic multiplying prefixes
1049           P-70.3.3    Order of citing suffixes and endings
1050       P-70.4General Rules for the Selection of Preferred Names
1051   P-71Radicals
1051       P-71.1General Methodology
1051       P-71.2Radicals Derived from Parent Hydrides
1051           P-71.2.1    Monovalent radicals
1053           P-71.2.2    Divalent and trivalent radicals
1055           P-71.2.3    Multiple radical centers (Polyradicals)
1056           P-71.2.4    Acyclic radicals derived by the removal of one or more hydrogen atoms from nonterminal chain positions
1056           P-71.2.5    The λ-convention
1056           P-71.2.6    ‘Added indicated hydrogen’
1057       P-71.3Radical Centers on Characteristic Groups
1057           P-71.3.1    Acyl radicals
1059           P-71.3.2    Removal of hydrogen atoms from an amine, imine, or amide characteristic group
1060           P-71.3.3    Polyamine, polyimine and polyamide radicals
1061           P-71.3.4    Removal of the hydrogen atom of a hydroxy group (or chalcogen analogue) of an acid or hydroxy compound
1062       P-71.4Assemblies of Parent Radicals
1063       P-71.5Prefixes Denoting Radicals
1064       P-71.6Order of Citation and Seniority of Suffixes ‘yl’, ‘ylidene’, and ‘ylidyne’
1064       P-71.7Choice of Parent Radical
1065   P-72Anions
1065       P-72.1General Methodology
1066       P-72.2Anions Formed by Removal of Hydrons
1066           P-72.2.1    Functional class nomenclature
1067           P-72.2.2    Systematic nomenclature
1067             P-        Anions derived from parent hydrides and their derivatives
1069             P-        Anions derived from characteristic groups
1069             P-            Anions derived from acids
1071             P-            Anions derived from hydroxy compounds
1072             P-            Anions derived from amines and imines
1073             P-            Anions derived from other characteristic groups
1074       P-72.3Anions Formed by Addition of Hydride Ions
1076       P-72.4Skeletal Replacement (‘a’) Nomenclature
1077       P-72.5Multiple Anionic Centers
1077           P-72.5.1    Assemblies of parent anions
1078           P-72.5.2    ‘Ide’ and ‘uide’ centers in the same parent hydride
1078           P-72.5.3    Anionic characteristic groups on anionic parent hydrides
1078       P-72.6Anionic Centers in Both Parent Compounds and Substituent Groups
1079           P-72.6.1    Prefixes for anionic centers derived from acid characteristic groups
1079           P-72.6.2    Prefixes for anionic chalcogens
1079           P-72.6.3    Systematically formed prefixes that include anionic center(s)
1080       P-72.7Choice of an Anionic Parent Structure
1081       P-72.8The Suffixes ‘ide’ and ‘uide’ and the λ-Convention
1081           P-72.8.1    The suffix ‘uide’ is preferred to the suffix ‘ide’ with a parent hydride named by the λ-convention
1082           P-72.8.2    The suffix ‘ide’ is preferred to the suffix ‘uide’ involved with the λ-convention
1082   P-73Cations
1082       P-73.0Introduction
1083       P-73.1Cationic Compounds with Cationic Centers Derived Formally by Addition of Hydrons
1083           P-73.1.1    Cationic centers in parent hydrides
1085           P-73.1.2    Cationic centers on characteristic groups
1085             P-        Cationic compounds derived from neutral compounds expressed by suffixes
1088             P-        Uronium ions and chalcogen analogues
1089       P-73.2Cationic Compounds with Cationic Centers Derived Formally by the Removal of Hydride Ions
1089           P-73.2.1    Functional class names
1089           P-73.2.2    Cationic centers in parent hydrides
1089             P-        Cationic centers in parent hydrides
1091             P-        ‘Added indicated hydrogen’
1092             P-        Diazonium ions
1093           P-73.2.3    Cationic centers on characteristic groups
1095       P-73.3The λ-Convention with the Suffix ‘ylium’
1095           P-73.3.1    Application of the λ-convention with the suffix ‘ylium’
1096           P-73.3.2    Retained names
1098       P-73.4Skeletal Replacement (‘a’) Nomenclature for Cations
1100       P-73.5Cationic Compounds with Multiple Cationic Centers
1100           P-73.5.1    Assemblies of parent cations
1103           P-73.5.2    ‘Ium’ and ‘ylium’ centers in the same parent hydride
1103           P-73.5.3    Cationic characteristic groups on parent cations
1104       P-73.6Cationic Prefix Names
1106       P-73.7Choice of a Parent Structure
1106           P-73.7.1    A parent cationic structure
1107       P-73.8The Suffixes ‘ium’ vs. ‘ylium’ and the λ-convention
1107           P-73.8.1    The suffix ‘-ylium’ is preferred to the suffix ‘-ium’ with a parent hydride modified by the λ-convention
1107           P-73.8.2    The suffix ‘ium’ is preferred to the suffix ‘ylium’ with a parent hydride modified by the λ-convention
1108   P-74Zwitterions
1108       P-74.0Introduction
1108       P-74.1Zwitterionic Parent Structures having the Anionic and Cationic centers on the same Parent Compound Including Ionic Centers on Characteristic Groups Expressible as Suffixes.
1108           P-74.1.1    Ionic centers in the same parent structure
1110           P-74.1.2    Zwitterionic compounds with at least one ionic center on a characteristic group
1111           P-74.1.3    Anionic and cationic centers on different parent structures
1111       P-74.2Dipolar Ions
1111           P-74.2.1    1,2-Dipolar compounds
1111             P-        ‘Ylides’
1113             P-        Amine oxides, imine oxides, and their chalcogen analogues
1113             P-        Amine imides
1114             P-        Phosphine oxides and chalcogen analogues
1114             P-        Phosphine imides
1115           P-74.2.2    1,3-Dipolar compounds
1115             P-        Allyl type compounds with delocalized general structure
1118             P-        The propargyl (propynyl) type including compounds with canonical resonance forms
1120             P-        The carbene type including compounds having with canonical resonance forms
1121           P-74.2.3    Dipolar substituent groups
1121   P-75Radical Ions
1122       P-75.1Radical Ions Formed by the Addition or Removal of of Electrons
1122       P-75.2Radical Ions Derived from Parent Hydrides
1123           P-75.2.1    Examples of radical anions
1123           P-75.2.2    Examples of radical cations
1124           P-75.2.3    Examples of zwitterionic radical ions
1124           P-75.2.4    ‘Added indicated hydrogen’
1125       P-75.3Radical Ions on Characteristic Groups
1125           P-75.3.1    Radical ions on ionic suffix groups
1126           P-75.3.2    Radical ions other than those named by using ionic suffix groups
1126       P-75.4Ionic and Radical Centers in Different Parent Structures
1127   P-76Delocalized Radicals and Ions
1127       P-76.1Delocalization in Names Involving One Radical or Ionic Center in an Otherwise Conjugated Double Bonds Structure is Denoted by the Appropriate Suffix without Locants
1127   P-77Salts
1127       P-77.1Preferred Names for Salts of Organic Bases
1127           P-77.1.1    Preferred IUPAC names for salts of organic bases are binary names
1127           P-77.1.2    Substitutive nomenclature is used to derive preferred IUPAC names for monosalts of di- or polyamines
1128           P-77.1.3    Traditional methods of naming salts of organic base when P-77.1.2 cannot be applied/td>
1128       P-77.2Salts Derived from Alcohols (including Phenols), Peroxols, and their Chalcogen Analogues
1128           P-77.2.1    Preferred IUPAC names are binary names formed by citing the name of the cation followed by that of the anion
1128           P-77.2.2    Substitutive nomenclature is used to derive IUPAC preferred names for monosalts of polyhydroxy compounds
1129       P-77.3Salts Derived from Organic Acids
1129           P-77.3.1    Preferred IUPAC names are binary names formed by citing the name of the cation followed by that of the anion
1129           P-77.3.2    Substitutive nomenclature is used to derive preferred IUPAC names for acid salts of polybasic organic acids
1130   P-80Introduction
1130   P-81Symbols and Definitions
1130       P-81.1Nuclide Symbols
1130       P-81.2Atomic Symbols
1131       P-81.3Names for Hydrogen Atoms and Ions
1131       P-81.4Isotopically Unmodified Compounds
1131       P-81.5Isotopically Modified Compounds
1131   P-82Isotopically Substituted Compounds
1132       P-82.0Introduction
1132       P-82.1Formulas
1132       P-82.2Names
1132           P-82.2.1    Isotopically substituted compounds
1134           P-82.2.2    Isotopically modified compounds
1135           P-82.2.3    Addition of hydro prefixes
1136           P-82.2.4    Location of isotopic descriptor in a two or more word name
1137           P-82.2.5    Location of isotopic descriptor in a one word name
1137       P-82.3Order of Nuclide Symbols
1137           P-82.3.1    When isotopes of different elements are present as nuclides
1138           P-82.3.2    When several isotopes of the same element are present as nuclides
1138       P-82.4Stereoisomeric Isotopically Substituted Compounds
1138           P-82.4.1    When stereoisomerism results from isotopic substitution
1139           P-82.4.2    Isotopically substituted stereoisomers
1140       P-82.5Numbering
1140           P-82.5.1    Numbering in relation to the unmodified compound
1140           P-82.5.2    Priority between isotopically substituted and unmodified atoms or groups
1141       P-82.6Locants
1141           P-82.6.1    Omission of locants
1142           P-82.6.2    Letter and/or numeral locants
1143           P-82.6.3    Location of nuclides on positions not normally denoted by locants
1144           P-82.6.4    Italicized nuclide symbols and/or italic capital letters to distinguish between different nuclides of the same element
1144   P-83Isotopically Labeled Compounds
1145       P-83.1Specifically Labeled Compounds
1145           P-83.1.1    Structures of specifically labeled compounds
1146           P-83.1.2    Names of specifically labeled compounds
1149       P-83.2Selectively Labeled Compounds
1149           P-83.2.1    Structures of selectively labeled compounds
1151           P-83.2.2    Names of selectively labeled compounds
1152       P-83.3Nonselectively Labeled Compounds
1152           P-83.3.1    Nonselectively labeled compounds
1152           P-83.3.2    Structures
1152           P-83.3.3    Names
1153       P-83.4Isotopically Deficient Compounds
1153           P-83.4.1    Isotopically deficient compounds
1153           P-83.4.2    Structures
1153           P-83.4.3    Names
1153       P-83.5General and Uniform Labeling
1153           P-83.5.1    Selectively labeled compound, all positions labeled, not necessarily evenly; the symbol ‘G’
1154           P-83.5.2    Selectively labeled compound, all positions uniformly labeled; the symbol ‘U’
1154           P-83.5.3    Selectively labeled compound. uniformly labelled at specified positions
1155   P-84Comparative Examples of Formulas and Names of Isotopically Modified Compounds
1156   P-90Introduction
1156   P-91Stereoisomer Graphical Representation and Naming
1157       P-91.1Stereoisomer Graphical Representation
1157       P-91.2Stereodescriptors
1157           P-91.2.1    Recommended stereodescriptors
1160           P-91.2.2    Omission of stereodescriptors
1160       P-91.3Naming of Stereoisomer
1162   P-92CIP Priority and Sequence Rules
1162       P-92.1The Cahn-Ingold-Prelog (CIP) System: General Methodology
1162           P-92.1.1    Stereogenic units
1165           P-92.1.2    Rules for the assignment of configuration
1168           P-92.1.3    The Sequence Rules
1169           P-92.1.4    Hierarchical digraphs
1170             P-        Acyclic molecules
1171             P-        Double and triple bonds
1172             P-        Saturated rings and ring systems
1173             P-        Mancude rings and ring systems
1174           P-92.1.5    Exploration of a hierarchical digraph
1175           P-92.1.6    Ligand ranking: application of the five Sequence Rules
1176       P-92.2Sequence Rule 1
1176           P-92.2.1    Sequence subrule 1a: Ligands are arranged in order of decreasing atomic number
1176             P-        Saturated compounds
1181             P-        Double and triple bonds
1183             P-        Saturated rings and ring systems
1186           P-92.2.2    Sequence Subrule 1b: Priority due to duplicate atoms
1188       P-92.3Sequence Rule 2: Higher atomic mass number precedes lower atomic mass number
1189       P-92.4Sequence Rule 3
1189           P-92.4.1    ‘seqcis’ = (‘Z’) and ‘seqtrans’ = (‘E’)
1190           P-92.4.2    Sequence Rule 3: ‘seqcis’ (‘Z’) precedes ‘seqtrans’ (‘E’) and this order precedes nonstereogenic double bonds
1193       P-92.5Sequence Rule 4
1194           P-92.5.1    Sequence Rule 4a: Chiral stereogenic units precede pseudoasymmetric and these precede nonstereogenic units
1195           P-92.5.2    Sequence Rule 4b: Like descriptor pairs have priority over unlike descriptor pairs
1204           P-92.5.3    Sequence rule 4c: ‘r’ precedes ‘s
1205       P-92.6Sequence Rule 5: ‘R’ precedes ‘S’, ‘M’ precedes ‘P’, and ‘seqCis’ precedes ‘seqTrans
1210   P-93Configuration Specification
1210       P-93.0Introduction
1210       P-93.1General Aspects of Configuration Specification
1210           P-93.1.1    Absolute configuration
1211           P-93.1.2    Relative configuration
1212           P-93.1.3    Racemates
1213           P-93.1.4    The descriptor ‘ambo
1213       P-93.2Tetrahedral Configuration of Atoms other than Carbon
1214           P-93.2.0    Introduction
1214           P-93.2.1    General methodogy
1214           P-93.2.2    Azanium (ammonium) and phosphanium (phosphonium) salts
1215           P-93.2.3    Amine oxides and phosphine oxides
1215           P-93.2.4    Phosphates, phosphonates, and related compounds
1216           P-93.2.5    Sulfates, sulfonates, and related compounds
1217           P-93.2.6    Compounds of Group 14 (other than carbon compounds)
1217       P-93.3Nontetrahedral Configuration
1217           P-93.3.1    General methodology
1218           P-93.3.2    Polyhedral symbols
1220           P-93.3.3    Configuration index and priority number
1220             P-        General methodology
1220             P-        Trigonal pyramid
1221             P-        T-shape systems
1222             P-        See-saw systems
1222             P-        Trigonal bipyramid
1223             P-        Square pyramid
1225             P-        Octahedron
1226           P-93.3.4    Chirality symbols
1227             P-        The chirality symbols ‘R/S
1227             P-        The chirality symbols ‘A’ and ‘C
1231       P-93.4Configuration Specification of Acyclic Organic Compounds
1231           P-93.4.1    Specification of stereogenic centers
1235           P-93.4.2    Specification of configuration for double bonds
1240       P-93.5Configuration Specification of Cyclic Organic Compounds
1241           P-93.5.0    Introduction
1241           P-93.5.1    Monocyclic compounds
1241             P-        Specification of stereogenic centers: stereodescriptors ‘R’, ‘S’, ‘r’, and ‘s
1244             P-        Relative configuration: stereodescriptors ‘cis’ and ‘trans
1246             P-        Relative configuration: stereodescriptors ‘r’, ‘c’, and ‘t
1248             P-        Unsaturated alicyclic compounds
1253           P-93.5.2    von Baeyer compounds
1253             P-        Specification of stereogenic centers by CIP stereodescriptors
1255             P-        Relative configuration (‘endo’, ‘exo’, ‘syn’, ‘anti’, ‘cis’, ‘trans’)
1257             P-        Specification of double bonds
1259           P-93.5.3    Spiro compounds
1259             P-        Specification of stereogenic spiro atoms of the type ‘Xabcd’, here ‘a’ > ‘b’ > ‘c’ > ‘d’
1261             P-        Specification of stereogenic spiro atoms of the type ‘Xabab’, where ‘a’ > ‘b’
1263             P-        Specification of double bonds
1263             P-        Specification of nontetrahedral stereogenic centers
1264             P-        Axial chirality of spiro compounds
1265           P-93.5.4    Fused and bridged fused compounds
1266             P-        Specification of configuration by CIP stereodescriptors
1268             P-        The descriptors ‘cisoid’ and ‘transoid
1269           P-93.5.5    Cyclophanes
1269             P-        Specification of stereogenic planes
1272             P-        Specification of chiral centers
1272             P-        Specification of double bonds
1272           P-93.5.6    Fullerenes
1272             P-        Definitions and general methodology
1273             P-        Type 1. Inherently chiral parent fullerenes
1274             P-        Type 2. Substituted fullerenes inherently chiral because of their substitution pattern
1275             P-        Type 3. Substituted fullerenes noninherently chiral because of their substitution pattern
1276             P-        Type 4. Chirality due to chiral substituents
1277             P-        Superimposition of stereogenic elements in a fullerene molecule
1278           P-93.5.7    Ring assemblies
1278             P-        Specification of stereogenic axes
1280             P-        Specification of stereogenic centers
1282             P-        Specification of double bonds in unsaturated rings and ring systems
1282       P-93.6Compounds Composed of Rings and Chains
1286   P-94Conformation and Conformational Stereodescriptors
1286       P-94.1Definition
1286       P-94.2Torsion Angle
1286           P-94.2.1    Torsion angle ‘X-A-B-Y’
1288           P-94.2.2    If ‘A’ and ‘B’ in ‘X-A-B-Y’ are trigonal centers, a lone pair of electrons
1289       P-94.3Specific Stereodescriptors
1289           P-94.3.1    Eclipsed, staggered and gauche (or skew) conformations
1290           P-94.3.2    Stereodescriptors for denoting the conformations of alicyclic rings
1293   P-100Introduction
1294   P-101Nomenclature for Natural Products Based on Parent Hydrides
(Alkaloids, Steroids, Terpenes, Carotenes, Corrinoids, Tetrapyrroles, and Similar Compounds)
1294       P-101.1Biologically Based Trivial Names
1294           P-101.1.1    Trivial name of a compound isolated from a natural source
1294           P-101.1.2    The ending ‘une’ or ‘iune’
1295       P-101.2Semisystematic Nomenclature for Natural Products (Stereoparent Hydrides)
1295           P-101.2.0    Introduction
1295           P-101.2.1    General guidelines for choosing a parent structure
1295           P-101.2.2    Structural features allowed for parent structures
1296           P-101.2.3    Numbering of parent structures
1297           P-101.2.4    Identification of individual rings
1297           P-101.2.5    Atomic connector, terminal segment and bond connector
1298           P-101.2.6    Stereochemical configuration of parent structures
1300           P-101.2.7    Semisystematic names of recommended fundamental parent structures
1302       P-101.3Skeletal Modifications of Parent Structures
1303           P-101.3.0    Introduction
1303           P-101.3.1    Removal of skeletal atoms
1305           P-101.3.2    Addition of skeletal atoms
1308           P-101.3.3    Bond formation
1310           P-101.3.4    Bond cleavage
1312           P-101.3.5    Bond migration
1313           P-101.3.6    Terminal ring removal
1314           P-101.3.7    Combination of the prefixes ‘cyclo’, ‘seco’, ‘apo’, ‘homo’, and ‘nor’
1317       P-101.4Replacement of Skeletal Atoms
1317           P-101.4.1    General methodology
1318           P-101.4.2    Skeletal replacement of carbon atoms by heteroatoms
1318           P-101.4.3    Skeletal replacement of heteroatoms by carbon atoms
1319           P-101.4.4    Skeketal replacement of heteroatoms by other heteroatoms
1319           P-101.4.5    Indicated hydrogen
1320       P-101.5Addition of Rings and Ring Systems
1320           P-101.5.1    Mancude rings and ring systems incorporated by fusion nomenclature
1323           P-101.5.2    Rings and ring systems incorporated by bridged fused ring nomenclature
1326           P-101.5.3    Rings and ring systems incorporated by spiro nomenclature
1327       P-101.6Modification of the Degree of Hydrogenation of Parent Structures
1327           P-101.6.1    By changing ‘an’ or ‘ane’ to ‘ene’ or ‘yne’
1328           P-101.6.2    The descriptors ‘E’ and ‘Z
1329           P-101.6.3    The prefix ‘all’ is used in front of stereodescriptors
1330           P-101.6.4    Double bonds in a parent structure modified by the prefix ‘hydro’
1330           P-101.6.5    Carbocyclic or heterocyclic ring components fused to a parent structure saturated using ‘hydro’ prefixes
1331           P-101.6.6    Additional unsaturation in a parent structure by the prefix ‘dehydro’
1332           P-101.6.7    Rearrangement of double bonds by a combination of ‘hydro’ and ‘dehydro’ prefixes
1333       P-101.7Derivatives of Parent Structures
1333           P-101.7.1    The suffixes and prefixes of organic nomenclature and the stereodescriptors α, β, and ξ
1337           P-101.7.2    Modifications of principal characteristic groups
1338           P-101.7.3    Substituent groups derived from parent structures by the suffixes ‘yl’, ‘ylidene’, or ‘ylidyne’
1338           P-101.7.4    Addition of rings denoting functional groups
1339           P-101.7.5    The prefix ‘de’ (not ‘des’), followed by the name of a group or atom
1341       P-101.8Further Aspects of Configurational Specification
1341           P-101.8.1    Inversion of configuration
1342           P-101.8.2    Racemates
1342           P-101.8.3    Relative configuration
1342           P-101.8.4    The stereodescriptors ‘R’ and ‘S’ for absolute configuration of an achiral parent structure and after ring opening
1344   P-102Carbohydrate Nomenclature
1344       P-102.1Definitions
1344           P-102.1.1    Carbohydrates
1344           P-102.1.2    Monosaccharides
1346           P-102.1.3    Oligosaccharides
1346           P-102.1.4    Polysaccharides
1346       P-102.2Parent Monosaccharides
1346           P-102.2.1    Parent aldoses and ketoses with up to six carbon atoms
1349           P-102.2.2    Numbering parent structures
1349       P-102.3Configurational Symbolism
1349           P-102.3.1    The Fischer projection of the acyclic form
1349           P-102.3.2    The stereodescriptors ‘D’ and ‘L
1350           P-102.3.3    The configurational atom
1350           P-102.3.4    Cyclic forms of monosaccharides
1353           P-102.3.5     Conformation of monosaccharides
1353           P-102.3.6    The Mills depiction
1354           P-102.3.7    Stereodescriptors for denoting racemates and uncertain configurations
1355       P-102.4Choice of a Parent Structure
1356       P-102.5Monosaccharides: Aldoses and Ketoses; Deoxy and Amino Sugars
1356           P-102.5.1    Aldoses
1358           P-102.5.2    Ketoses
1361           P-102.5.3    Deoxy sugars
1363           P-102.5.4    Amino sugars
1365           P-102.5.5    Thio sugars
1366           P-102.5.6    Substituted monosaccharides
1366             P-        O-substitution
1369             P-        Glycosides
1370             P-        C-Substitution
1372             P-        N-substitution
1373             P-        Alditols
1376             P-        Carboxylic acids derived from monosaccharides
1382             P-        Anhydrides
1383       P-102.6Monosaccharides and Derivatives as Substituent Groups
1383           P-102.6.1    Glycosyl groups
1388       P-102.7Disaccharides and Oligosaccharides
1388           P-102.7.1    Disaccharides
1389           P-102.7.2    Oligosaccharides
1391   P-103Amino Acids and Peptides
1391       P-103.0Introduction
1391       P-103.1Names, Numbering and Configuration Specification of Amino Acids
1392           P-103.1.1    Retained and systematic names
1392             P-        Retained names of the ‘common’ amino acids
1394             P-        Retained names of ‘less common’ amino acids
1396             P-        Systematic substitutive names
1396           P-103.1.2    Numbering of α-amino carboxylic acids
1397           P-103.1.3    Configuration of α-amino carboxylic acids
1399       P-103.2Derivatives of Amino Acids
1399           P-103.2.1    System for denoting locants
1401           P-103.2.2    Names of substituent groups
1402           P-103.2.3    Derivatives formed by substitution
1404           P-103.2.4    Ionization of characteristic groups
1405           P-103.2.5    Acyl groups
1406           P-103.2.6    Esters
1406           P-103.2.7    Amides and other nitrogenous derivatives
1407           P-103.2.8    Aldehydes, ketones and alcohols
1408       P-103.3Nomenclature of Peptides
1408           P-103.3.1    Definitions
1408           P-103.3.2    Names of peptides
1409           P-103.3.3    Symbols of peptides
1409           P-103.3.4    Indication of configuration in peptides
1409           P-103.3.5    Modification of named peptides
1410             P-        Replacement of residues
1412             P-        Extension of the peptide chain
1413             P-        Insertion of residues
1413             P-        Removal of residues
1414           P-103.3.6    Cyclic peptides
1414   P-104Cyclitols
1414       P-104.0Introduction
1414       P-104.1Definitions
1415       P-104.2Name Construction
1415           P-104.2.1    Stereoisomeric inositols
1416           P-104.2.2    Cyclitols other than inositols
1416           P-104.2.3    Numbering on cyclitols
1418       P-104.3Derivatives of Cyclitols
1418           P-104.3.1    Derivatives of inositols
1419           P-104.3.2    Derivatives of cyclitols other than inositols
1419   P-105Nucleosides
1419       P-105.0Introduction
1421       P-105.1Retained Names of Nucleosides
1422       P-105.2Substitution on Nucleosides
1422           P-105.2.1    Substitution of nucleosides
1424           P-105.2.2    Nomenclature when a higher priority characteristic group is present
1425   P-106Nucleotides
1425       P-106.0Introduction
1425       P-106.1Retained Names
1425       P-106.2Nucleotide Diphosphates and Triphosphates
1427       P-106.3Derivatives of Nucleotides
1427           P-106.3.1    Nucleotides having retained names
1428           P-106.3.2    Analogues of nucleoside di- and polyphosphates
1429           P-106.3.3    Nomenclature when a higher priority characteristic group is present
1430           P-106.3.4    Oligonucleotides
1431           P-106.3.5    Nucleotides with phosphorothioic acid
1431   P-107Lipids
1430       P-107.0Introduction
1432       P-107.1Definitions
1432       P-107.2Glycerides
1433       P-107.3Phosphatidic Acids
1433           P-107.3.1    Phosphatidic acids
1433           P-107.3.2    Configuration of phosphatidic acids
1434           P-107.3.3    Phosphatidylserines
1434           P-107.3.4    Phosphatidylcholines
1435           P-107.3.5    Phosphatidylethanolamine
1435           P-107.3.6    Phosphatidylinositols
1436       P-107.4Glycolipids
1436           P-107.4.1    Definitions
1436           P-107.4.2    Glycoglycerolipids
1436           P-107.4.3    Glycosphingolipids
1443Appendix 1 Seniority list of elements and ‘a’ terms used in skeletal replacement (‘a’) nomenclature
1445Appendix 2 Detachable prefixes used in substitutive nomenclature
1515Appendix 3 Structures for alkaloids, steroids, terpenoids and similar compounds
15151.   Alkaloids
15272.   Steroids
15313.   Terpenoids
15414.   Miscellaneous

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