Basic Organic Stereochemistry

ISBN-10: 0471374997
ISBN-13: 9780471374992
Edition: 2001
List price: $188.00 Buy it from $99.99
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Description: This title explains the fundamental concepts and principles of stereochemistry, offers treatment of conformational analysis, and summarises properties of stereoisomers and their separation.

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Book details

List price: $188.00
Copyright year: 2001
Publisher: John Wiley & Sons, Incorporated
Publication date: 4/11/2001
Binding: Paperback
Pages: 704
Size: 6.00" wide x 9.00" long x 1.25" tall
Weight: 2.090
Language: English

This title explains the fundamental concepts and principles of stereochemistry, offers treatment of conformational analysis, and summarises properties of stereoisomers and their separation.

Preface
Introduction
Scope
History
Polarimetry and Optical Rotation
References
Structure
Meaning, Factorization, Internal Coordinates, Isomers
Constitution
Configuration
Conformation
Determination of Structure
A Priori Calculation of Structure
Molecular Models
References
Stereoisomers
Nature of Stereoisomers
General
Barriers Between Stereoisomers and Residual Stereoisomers
Enantiomers
Diastereomers
General Cases
Degenerate Cases
References
Symmetry
Introduction
Symmetry Elements
Symmetry Operators and Symmetry Point Groups
Point Groups Containing Chiral Molecules
Point Groups Containing Only Achiral Molecules
Averaged Symmetry
Symmetry and Molecular Properties
Rotation of Polarized Light
Dipole Moment
Symmetry Number
References
Configuration
Definitions: Relative and Absolute Configuration
Absolute Configuration and Notation
Determination of Absolute Configuration
Bijvoet Method
Theoretical Approaches
Modification of Crystal Morphology in the Presence of Additives
Relative Configuration and Notation
Determination of Relative Configuration of Saturated Aliphatic Compounds
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
The Method of Quasi-Racemates
Chemical Correlations Affecting Bonds to a Chiral Atom in a "Known" Way (For an overview, see ref. 32.)
Correlation by Stereoselective Synthesis of "Known" Stereochemical Course
Chiroptical, Spectroscopic, and Other Physical Methods
Conclusion: Network Arguments
References
Properties of Stereoisomers and Stereoisomer Discrimination
Introduction
Stereoisomer Discrimination
The Nature of Racemates
Properties of Racemates and of Their Enantiomer Components
Introduction
Optical Activity
Crystal Shape
Density and Racemate Type
Melting Point
Solubility
Vapor Pressure
Infrared Spectra
Electronic Spectra
Nuclear Magnetic Resonance Spectra
X-Ray Spectra
Liquid State and Interfacial Properties
Chromatography
Mass Spectrometry
Interaction with Other Chiral Substances
Biological Properties
Origins of Enantiomeric Homogeneity in Nature
Determination of Enantiomer and Diastereomer Composition
Introduction
Chiroptical Methods
NMR Methods Based on Diastereotopicity
Chromatographic and Related Separation Methods Based on Diastereomeric Interactions
Kinetic Methods
Miscellaneous Methods
References
Separation of Stereoisomers, Resolution, and Racemization
Introduction
Separation of Enantiomers by Crystallization
Crystal Picking and Triage
Conglomerates
Preferential Crystallization
Asymmetric Transformation of Racemates and Total Spontaneous Resolution
Chemical Separation of Enantiomers via Diastereomers
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
Kinetic Resolution
Theory and Stoichiometric and Abiotic Catalytic Kinetic Resolution
Enzymatic Resolution
Miscellaneous Separation Methods
Racemization
Racemization Processes
Racemization of Amino Acids
References
Heterotopic Ligands and Faces: Prostereoisomerism and Prochirality
Introduction and Terminology
Significance and History
Homotopic and Heterotopic Ligands and Faces
Homotopic Ligands and Faces
Enantiotopic Ligands and Faces
Diastereotopic Ligands and Faces
Concepts and Nomenclature
Heterotopicity and Nuclear Magnetic Resonance
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
Heterotopicity and Stereoelective Synthesis
Heterotopicity and Enzyme-Catalyzed Reactions
References
Stereochemistry of Alkenes
Structure of Alkenes and Nature of cis-trans Isomerism
General
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
Chemical Methods
Physical Methods
Interconversion of cis-trans Isomers: Position of Equilibrium and Methods of Isomerization
Position of cis-trans Equilibria
Methods of Equilibration
Directed cis-trans Interconversion
References
Conformation of Acyclic Molecules
Conformation of Ethane, Butane, and Other Simple Saturated Acyclic Molecules
Alkanes
Saturated Acyclic Molecules with Polar Substituents or Chains and the Anomeric Effect
Conformation of Unsaturated Acyclic and Miscellaneous Compounds
Unsaturated Acyclic Compounds
Alkylbenzenes
Miscellaneous Compounds
Physical and Spectral Properties of Diastereomers and Conformers
General
Dipole Moments
Infrared Spectra
NMR Spectroscopy
Conformation and Reactivity: The Winstein-Holness Equation and the Curtin-Hammett Principle
References
Configuration and Conformation of Cyclic Molecules
Stereoisomerism and Configurational Nomenclature of Ring Compounds
Determination of Configuration of Substituted Ring Compounds
Introduction
Symmetry-Based Methods
Methods Based on Physical and Chemical Properties
Correlation Methods
Stability of Cyclic Molecules
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
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
Three-Membered Rings
Four-Membered Rings
Five-Membered Rings
Rings Larger Than Six-Membered
Stereochemistry of Fused, Bridged, and Caged Ring Systems
Fused Rings
Bridged Rings
Propellanes
Catenanes, Rotaxanes, Knots, and Mobius Strips
Cubane, Tetrahedrane, Dodecahedrane, Adamantane, and Buckminsterfullerene
References
Chiroptical Properties
Introduction
Optical Activity and Anisotropic Refraction
Origin and Theory
Optical Rotatory Dispersion
Circular Dichroism and Anisotropic Absorption
Applications of Optical Rotary Dispersion and Circular Dichroism
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
Polarimetry
Empirical Rules and Correlations: Calculation of Optical Rotation
Vibrational Optical Activity
References
Chirality in Molecules Devoid of Chiral Centers
Introduction and Nomenclature
Allenes
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
Spiranes
Biphenyls and Atropisomerism
Introduction
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
Helicenes
Molecules with Planar Chirality
Introduction
Cyclophanes
trans-Cycloalkenes
Metallocenes and Related Compounds
References
Index

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