| Preface |
| Introduction / 1： |
| Scope / 1-1.： |
| History / 1-2.： |
| Polarimetry and Optical Rotation / 1-3.： |
| References |
| Structure / 2： |
| Meaning, Factorization, Internal Coordinates, Isomers / 2-1.： |
| Constitution / 2-2.： |
| Configuration / 2-3.： |
| Conformation / 2-4.： |
| Determination of Structure / 2-5.： |
| A Priori Calculation of Structure / 2-6.： |
| Molecular Models / 2-7.： |
| Stereoisomers / 3： |
| Nature of Stereoisomers / 3-1.： |
| General / a.： |
| Barriers Between Stereoisomers and Residual Stereoisomers / b.： |
| Enantiomers / 3-2.： |
| Diastereomers / 3-3.： |
| General Cases |
| Degenerate Cases |
| Symmetry / 4： |
| Symmetry Elements / 4-1.： |
| Symmetry Operators and Symmetry Point Groups / 4-3.： |
| Point Groups Containing Chiral Molecules |
| Point Groups Containing Only Achiral Molecules |
| Averaged Symmetry / 4-4.： |
| Symmetry and Molecular Properties / 4-5.： |
| Rotation of Polarized Light |
| Dipole Moment |
| Symmetry Number / c.： |
| Definitions: Relative and Absolute Configuration / 5： |
| Absolute Configuration and Notation / 5-2.： |
| Determination of Absolute Configuration / 5-3.： |
| Bijvoet Method |
| Theoretical Approaches |
| Modification of Crystal Morphology in the Presence of Additives |
| Relative Configuration and Notation / 5-4.： |
| Determination of Relative Configuration of Saturated Aliphatic Compounds / 5-5.： |
| X-Ray Structure Analysis |
| Chemical Interconversion Not Affecting Bonds to the Stereogenic Atom |
| Methods Based on Symmetry Considerations |
| Correlation Via Compounds with Chiral Centers of Two Types / d.： |
| The Method of Quasi-Racemates / e.： |
| Chemical Correlations Affecting Bonds to a Chiral Atom in a "Known" Way (For an overview, see ref. 32.) / f.： |
| Correlation by Stereoselective Synthesis of "Known" Stereochemical Course / g.： |
| Chiroptical, Spectroscopic, and Other Physical Methods / h.： |
| Conclusion: Network Arguments / 5-6.： |
| Properties of Stereoisomers and Stereoisomer Discrimination / 6： |
| Stereoisomer Discrimination / 6-1.： |
| The Nature of Racemates / 6-3.： |
| Properties of Racemates and of Their Enantiomer Components / 6-4.： |
| Optical Activity |
| Crystal Shape |
| Density and Racemate Type |
| Melting Point |
| Solubility |
| Vapor Pressure |
| Infrared Spectra |
| Electronic Spectra / i.： |
| Nuclear Magnetic Resonance Spectra / j.： |
| X-Ray Spectra / k.： |
| Liquid State and Interfacial Properties / l.： |
| Chromatography / m.： |
| Mass Spectrometry / n.： |
| Interaction with Other Chiral Substances / o.： |
| Biological Properties / p.： |
| Origins of Enantiomeric Homogeneity in Nature / q.： |
| Determination of Enantiomer and Diastereomer Composition / 6-5.： |
| Chiroptical Methods |
| NMR Methods Based on Diastereotopicity |
| Chromatographic and Related Separation Methods Based on Diastereomeric Interactions |
| Kinetic Methods |
| Miscellaneous Methods |
| Separation of Stereoisomers, Resolution, and Racemization / 7： |
| Separation of Enantiomers by Crystallization / 7-1.： |
| Crystal Picking and Triage |
| Conglomerates |
| Preferential Crystallization |
| Asymmetric Transformation of Racemates and Total Spontaneous Resolution |
| Chemical Separation of Enantiomers via Diastereomers / 7-3.： |
| Formation and Separation of Diastereomers; Resolving Agents |
| Resolution Principles and Practice |
| Separation Via Complexes and Inclusion Compounds |
| Chromatographic Resolution |
| Asymmetric Transformations of Diastereomers |
| General Methods for the Separation of Diastereomers |
| Enantiomeric Enrichment and Resolution Strategy / 7-4.： |
| Kinetic Resolution / 7-5.： |
| Theory and Stoichiometric and Abiotic Catalytic Kinetic Resolution |
| Enzymatic Resolution |
| Miscellaneous Separation Methods / 7-6.： |
| Racemization / 7-7.： |
| Racemization Processes |
| Racemization of Amino Acids |
| Heterotopic Ligands and Faces: Prostereoisomerism and Prochirality / 8： |
| Introduction and Terminology / 8-1.： |
| Significance and History / 8-2.： |
| Homotopic and Heterotopic Ligands and Faces / 8-3.： |
| Homotopic Ligands and Faces |
| Enantiotopic Ligands and Faces |
| Diastereotopic Ligands and Faces |
| Concepts and Nomenclature |
| Heterotopicity and Nuclear Magnetic Resonance / 8-4.： |
| General Principles. Anisochrony |
| NMR in Assignment of Configuration and of Descriptors of Prostereoisomerism |
| Origin of Anisochrony |
| Conformationally Mobile Systems |
| Heterotopic Ligands and Faces in Enzyme-Catalyzed Reactions / 8-5.： |
| Heterotopicity and Stereoelective Synthesis |
| Heterotopicity and Enzyme-Catalyzed Reactions |
| Stereochemistry of Alkenes / 9： |
| Structure of Alkenes and Nature of cis-trans Isomerism / 9-1.： |
| Nomenclature |
| Cumulenes |
| Alkenes with Low Rotational Barriers and Nonplanar Alkenes |
| The C=N and N=N Double Bonds |
| Determination of Configuration of cis-trans Isomers / 9-2.： |
| Chemical Methods |
| Physical Methods |
| Interconversion of cis-trans Isomers: Position of Equilibrium and Methods of Isomerization / 9-3.： |
| Position of cis-trans Equilibria |
| Methods of Equilibration |
| Directed cis-trans Interconversion |
| Conformation of Acyclic Molecules / 10： |
| Conformation of Ethane, Butane, and Other Simple Saturated Acyclic Molecules / 10-1.： |
| Alkanes |
| Saturated Acyclic Molecules with Polar Substituents or Chains and the Anomeric Effect |
| Conformation of Unsaturated Acyclic and Miscellaneous Compounds / 10-2.： |
| Unsaturated Acyclic Compounds |
| Alkylbenzenes |
| Miscellaneous Compounds |
| Physical and Spectral Properties of Diastereomers and Conformers / 10-3.： |
| Dipole Moments |
| NMR Spectroscopy |
| Conformation and Reactivity: The Winstein-Holness Equation and the Curtin-Hammett Principle / 10-4.： |
| Configuration and Conformation of Cyclic Molecules / 11： |
| Stereoisomerism and Configurational Nomenclature of Ring Compounds / 11-1.： |
| Determination of Configuration of Substituted Ring Compounds / 11-2.： |
| Symmetry-Based Methods |
| Methods Based on Physical and Chemical Properties |
| Correlation Methods |
| Stability of Cyclic Molecules / 11-3.： |
| Strain |
| Ease of Cyclization as a Function of Ring Size |
| Ease of Ring Closure as a Function of the Ring Atoms and Substitutents: The Thorpe-Ingold Effect |
| Baldwin's Rules |
| Conformational Aspects of the Chemistry of Six-Membered Ring Compounds / 11-4.： |
| Cyclohexane |
| Monosubstituted Cyclohexanes |
| Disubstituted and Polysubstituted Cyclohexanes |
| Conformation and Physical Properties in Cyclohexane Derivatives |
| Conformation and Reactivity in Cyclohexanes |
| sp[superscript 2] Hybridized Cyclohexyl Systems |
| Six-Membered Saturated Heterocycles |
| Chemistry of Ring Compounds Other than Six-Membered Ones / 11-5.： |
| Three-Membered Rings |
| Four-Membered Rings |
| Five-Membered Rings |
| Rings Larger Than Six-Membered |
| Stereochemistry of Fused, Bridged, and Caged Ring Systems / 11-6.： |
| Fused Rings |
| Bridged Rings |
| Propellanes |
| Catenanes, Rotaxanes, Knots, and Mobius Strips |
| Cubane, Tetrahedrane, Dodecahedrane, Adamantane, and Buckminsterfullerene |
| Chiroptical Properties / 12： |
| Optical Activity and Anisotropic Refraction / 12-1.： |
| Origin and Theory |
| Optical Rotatory Dispersion |
| Circular Dichroism and Anisotropic Absorption / 12-3.： |
| Applications of Optical Rotary Dispersion and Circular Dichroism / 12-4.： |
| Determination of Configuration and Conformation: Theory |
| Classification of Chromophores |
| Sector and Helicity Rules |
| Exciton Chirality |
| Other Applications: Induced ORD and CD |
| Circular Dichroism of Chiral Polymers |
| Applications of Optical Activity / 12-5.： |
| Polarimetry |
| Empirical Rules and Correlations: Calculation of Optical Rotation |
| Vibrational Optical Activity / 12-6.： |
| Chirality in Molecules Devoid of Chiral Centers / 13： |
| Introduction and Nomenclature / 13-1.： |
| Allenes / 13-2.： |
| Historical Overview and Natural Occurrence |
| Synthesis of Optically Active Allenes |
| Determination of Configuration and Enantiomeric Purity of Allenes |
| Cyclic Allenes, Cumulenes, and Ketene Imines |
| Alkylidenecycloalkanes / 13.3.： |
| Spiranes / 13-4.： |
| Biphenyls and Atropisomerism / 13-5.： |
| Biphenyls and Other Atropisomers of the sp[superscript 2]-sp[superscript 2] Single-Bond Type |
| Atropisomerism About sp[superscript 2]-sp[superscript 3] Single Bonds |
| Atropisomerism About sp[superscript 3]-sp[superscript 3] Bonds |
| Molecular Propellers / 13-6.： |
| Helicenes / 13-7.： |
| Molecules with Planar Chirality / 13-8.： |
| Cyclophanes |
| trans-Cycloalkenes |
| Metallocenes and Related Compounds |
| Index |
