Basic Terminology of Stereochemistry
(IUPAC Recommendations 1996)

Contents

Quick move to A, B, C, D, E, F, G, H, I, K, L, M, N, O, P, Q, R, S, T, U, V, W,Z.


Synopsis.
Introduction
Graphic Representation of Three-Dimensional Structures
References

Absolute Configuration
ac See torsion angle.
Achiral See chirality.
Achirotopic See chirotopic.
[alpha] (Alpha), [beta] (Beta)
Ambo
Angle Strain
Anisometric See isometric.
Anomeric Effect
Anomers
Anti
Anticlinal See torsion angle.
Antiperiplanar See torsion angle.
Antipodes
ap See torsion angle.
Apical, Basal, Equatorial
Asymmetric
Asymmetric Carbon Atom
Asymmetric Centre See chirality centre.
Asymmetric Destruction See kinetic resolution.
Asymmetric Induction
Asymmetric Synthesis
Asymmetric Transformation
Atropisomers
Axial, Equatorial
Axial Chirality
Axis of Chirality See chirality axis.
Axis of Helicity See helicity.

Baeyer Strain See angle strain.
Basal See apical, basal, equatorial.
Berry Pseudorotation See pseudorotation.
[beta] (Beta) See [alpha] (alpha), [beta] (beta)
Bisecting Conformation, Eclipsing Conformation
Boat See chair, boat, twist; and half-chair, half-boat.
Bond Opposition Strain See eclipsing strain.
Bowsprit, Flagpole
Bredt's Rule

C.I.P. System
Cahn-Ingold-Prelog System See CIP Priority.
Centre of Chirality See chirality centre.
Chair, Boat, Twist
Chair-Chair Interconversion See ring reversal.
Chemical Species
Chiral
Chirality
Chirality Axis
Chirality Centre
Chirality Element
Chirality Plane
Chirality Sense
Chiroptic/Chiroptical
Chirotopic
CIP Priority
cis, trans
cisoid Conformation
cis-trans Isomers
Clinal See torsion angle.
Compensation
Configuration
Conformation
Conformational Analysis
Conformer
Conglomerate See racemic conglomerate.
Constitution
Constitutional Isomerism
Crown Conformation

D, L, DL See Fischer-Rosanoff convention.
d, l , dl
[Delta] (Delta), [Lambda] (Lambda)
Deracemisation See asymmetric transformation.
Desymmetrisation
Desymmetrisation Step
Diastereoisomerisation
Diastereoisomerism
Diastereoisomers (Diastereomers) See diastereoisomerism.
Diastereoisomer Excess/Diastereoisomeric Excess
Diastereomeric Ratio
Diastereomers See diastereoisomerism.
Diastereoselectivity See stereoselectivity.
Diastereomorphism
Diastereotopic
Dihedral Angle
Dissymmetry

E, Z
Eclipsed, Eclipsing
Eclipsing Conformation See bisecting conformation.
Eclipsing Strain
Element of Chirality See chirality element.
Enantioconvergence See stereoconvergence.
Enantioenriched See enantiomerically enriched
Enantiomer
Enantiomer Excess/Enantiomeric Excess
Enantiomeric Ratio
Enantiomerically Enriched/Enantioenriched
Enantiomerically Pure/Enantiopure
Enantiomeric Purity See enantiomer excess.
Enantiomerisation
Enantiomerism
Enantiomorph
Enantiopure See enantiomerically pure.
Enantioselectivity See stereoselectivity.
Enantiotopic
endo, exo, syn, anti
ent
Envelope Conformation
Epimerisation
Epimers
Equatorial
erythro, threo
exo See endo, exo, syn, anti.
External Compensation

Fiducial Group See helicity and torsion angle.
Fischer Projection (or Fischer-Tollens Projection)
Fischer-Rosanoff Convention (or Rosanoff Convention)
Flagpole See bowsprit, flagpole.
Free Rotation, Hindered Rotation, Restricted Rotation

Gauche
Gauche Effect
Geometric Isomerism

Half-chair
Handedness
Helicity
Heterotopic See stereoheterotopic.
Hindered Rotation See free rotation, hindered rotation, restricted rotation.
Homochiral See enantiomerically pure/enantiopure.
Homomorphic
Homotopic

In-Out Isomerism
Induction, Stereochemical See asymmetric induction.
Internal Compensation See meso-compound.
Inversion
Isomer
Isomeric
Isomerism
Isometric, Anisometric
Isotopomers

Kinetic Resolution

L See Fischer-Rosanoff Convention.
l
l, u
[Lambda] (Lambda) See [Delta](delta).

M See helicity.
meso
meso-Compound
Minus See plus, minus
Molecular Entity
Mutarotation

Newman Projection
Nonbonded Interactions

Optical Activity
Optical Antipodes
Optical Isomerism
Optical Purity
Optical Resolution See resolution.
Optical Rotation See optical activity.
Optical Yield
Optically Labile
Out-isomer See in-out isomerism.

P, M See helicity.
Percent Diastereoisomer Excess See diastereoisomer excess.
Percent Enantiomer Excess See enantiomer excess.
Periplanar See torsion angle.
Perspective Formula
Pitzer Strain See eclipsing strain.
Planar Chirality
Plus, Minus
Point Group
Polytopal Rearrangement
Primary Structure
Priority See CIP priority.
Prochirality
Prochirality Centre
pro-E, pro-Z
Projection Formula
Proprochirality See prochirality.
pro-R, pro-S
Pseudo-asymmetric Carbon Atom
Pseudo-axial See axial, equatorial.
Pseudo-equatorial See axial, equatorial.
Pseudorotation
Pyramidal Inversion

Quasi-axial See axial, equatorial.
Quasi-enantiomers
Quasi-equatorial See axial, equatorial.
Quasi-racemic Compound
Quaternary Structure

r, s
R, S
Rp, Sp See planar chirality.
R*, S* See relative configuration.
rac See racemate.
Racemate
Racemic
Racemic Compound
Racemic Conglomerate
Racemic Mixture
Racemisation
Re, Si
rel See relative configuration.
Relative Configuration
Resolution
Restricted Rotation See free rotation, hindered rotation, restricted rotation.
Retention of configuration See Walden inversion.
Ring Reversal (or ring inversion)
Rosanoff Convention See Fischer-Rosanoff convention.
Rotamer
Rotational Barrier
Rotatory Power
RS See racemate.

s-cis, s-trans
S See R, S.
Sawhorse Projection
sc See torsion angle.
Secondary Structure
Si See Re, Si.
Sequence Rules See priority.
Skew See torsion angle and chair, boat, twist.
sp See torsion angle.
Space Formula
Spontaneous Resolution See racemic conglomerate.
SR See racemate.
Staggered Conformation
Stereochemical Formula (Stereoformula)
Stereoconvergence
Stereodescriptor
Stereoelectronic
Stereoelectronic Control
Stereoformula See projection formula.
Stereogenic Unit (or Stereogen or Stereoelement)
Stereoheterotopic
Stereoisomerism
Stereoisomerism, Planar See planar chirality.
Stereoisomers
Stereomutation
Stereoselective synthesis
Stereoselectivity
Stereospecificity
Steric Strain
Superposability
Syn
Synclinal See torsion angle.
Synperiplanar See torsion angle.

Tertiary structure
threo See erythro.
Topomerisation
Topomers See topomerisation.
Torsion Angle
Torsional Stereoisomers
Torsional Strain See eclipsing strain.
trans See cis, trans.
Transannular Strain
transoid Conformation
Tub Conformation
Turnstile Rotation See pseudo-rotation.
Twist Form See chair, boat, twist.

u See l, u.

Valence Isomerism

Walden Inversion
Wedge Projection

Z See E, Z.
Zig-zag Projection


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