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Stereoisomers are compounds with the same chemical formula and connectivity but with different arrangements of their atoms in 3-dimensional space. Stereochemistry encompasses the study of stereoisomers and their properties. Despite having an identical chemical formula, stereoisomers can have drastically different biological, medicinal, and chemical properties. Basic Organic Stereochemistry explains in clear, concise terms the concepts and properties of stereoisomers.
Ideal both as a text for advanced undergraduate or graduate students and as a handy guide for researchers in industry, this superb text covers: Polarimetry and optical rotation
Internal coordinates, configuration, and conformation
Nature of stereoisomers
Barriers between stereoisomers and residual stereoisomers
Symmetry operators and symmetry point groups
Properties of stereoisomers and stereoisomer discrimination
Separation of stereoisomers, resolution, and racemization
Suitable for students in organic and biological chemistry, Basic Organic Stereochemistry is unparalleled as a convenient text.

Tabla de contenidos provista por Syndetics

• Preface(p. xiii)
• 1 Introduction(p. 1)
• 1-1. Scope(p. 1)
• 1-2. History(p. 1)
• 1-3. Polarimetry and Optical Rotation(p. 5)
• References(p. 7)
• 2 Structure(p. 8)
• 2-1. Meaning, Factorization, Internal Coordinates, Isomers(p. 8)
• 2-2. Constitution(p. 11)
• 2-3. Configuration(p. 13)
• 2-4. Conformation(p. 15)
• 2-5. Determination of Structure(p. 17)
• 2-6. A Priori Calculation of Structure(p. 20)
• 2-7. Molecular Models(p. 25)
• References(p. 26)
• 3 Stereoisomers(p. 30)
• 3-1. Nature of Stereoisomers(p. 30)
• a. General(p. 30)
• b. Barriers Between Stereoisomers and Residual Stereoisomers(p. 34)
• 3-2. Enantiomers(p. 36)
• 3-3. Diastereomers(p. 39)
• a. General Cases(p. 39)
• b. Degenerate Cases(p. 42)
• References(p. 44)
• 4 Symmetry(p. 45)
• 4-1. Introduction(p. 45)
• 4-2. Symmetry Elements(p. 45)
• 4-3. Symmetry Operators and Symmetry Point Groups(p. 48)
• a. Point Groups Containing Chiral Molecules(p. 49)
• b. Point Groups Containing Only Achiral Molecules(p. 51)
• 4-4. Averaged Symmetry(p. 58)
• 4-5. Symmetry and Molecular Properties(p. 59)
• a. Rotation of Polarized Light(p. 59)
• b. Dipole Moment(p. 61)
• c. Symmetry Number(p. 62)
• References(p. 63)
• 5 Configuration(p. 65)
• 5-1. Definitions: Relative and Absolute Configuration(p. 65)
• 5-2. Absolute Configuration and Notation(p. 67)
• 5-3. Determination of Absolute Configuration(p. 75)
• a. Bijvoet Method(p. 75)
• b. Theoretical Approaches(p. 77)
• c. Modification of Crystal Morphology in the Presence of Additives(p. 77)
• 5-4. Relative Configuration and Notation(p. 79)
• 5-5. Determination of Relative Configuration of Saturated Aliphatic Compounds(p. 84)
• a. X-Ray Structure Analysis(p. 85)
• b. Chemical Interconversion Not Affecting Bonds to the Stereogenic Atom(p. 86)
• c. Methods Based on Symmetry Considerations(p. 86)
• d. Correlation Via Compounds with Chiral Centers of Two Types(p. 89)
• e. The Method of Quasi-Racemates(p. 90)
• f. Chemical Correlations Affecting Bonds to a Chiral Atom in a "Known" Way (For an overview, see ref. 32.)(p. 90)
• g. Correlation by Stereoselective Synthesis of "Known" Stereochemical Course(p. 95)
• h. Chiroptical, Spectroscopic, and Other Physical Methods(p. 98)
• 5-6. Conclusion: Network Arguments(p. 98)
• References(p. 98)
• 6 Properties of Stereoisomers and Stereoisomer Discrimination(p. 102)
• 6-1. Introduction(p. 102)
• 6-2. Stereoisomer Discrimination(p. 102)
• 6-3. The Nature of Racemates(p. 106)
• 6-4. Properties of Racemates and of Their Enantiomer Components(p. 108)
• a. Introduction(p. 108)
• b. Optical Activity(p. 109)
• c. Crystal Shape(p. 109)
• d. Density and Racemate Type(p. 110)
• e. Melting Point(p. 111)
• f. Solubility(p. 115)
• g. Vapor Pressure(p. 119)
• h. Infrared Spectra(p. 120)
• i. Electronic Spectra(p. 121)
• j. Nuclear Magnetic Resonance Spectra(p. 122)
• k. X-Ray Spectra(p. 123)
• l. Liquid State and Interfacial Properties(p. 124)
• m. Chromatography(p. 128)
• n. Mass Spectrometry(p. 129)
• o. Interaction with Other Chiral Substances(p. 130)
• p. Biological Properties(p. 132)
• q. Origins of Enantiomeric Homogeneity in Nature(p. 138)
• 6-5. Determination of Enantiomer and Diastereomer Composition(p. 142)
• a. Introduction(p. 142)
• b. Chiroptical Methods(p. 145)
• c. NMR Methods Based on Diastereotopicity(p. 147)
• d. Chromatographic and Related Separation Methods Based on Diastereomeric Interactions(p. 160)
• e. Kinetic Methods(p. 176)
• f. Miscellaneous Methods(p. 178)
• References(p. 180)
• 7 Separation of Stereoisomers, Resolution, and Racemization(p. 197)
• 7-1. Introduction(p. 197)
• 7-2. Separation of Enantiomers by Crystallization(p. 198)
• a. Crystal Picking and Triage(p. 198)
• b. Conglomerates(p. 198)
• c. Preferential Crystallization(p. 201)
• d. Asymmetric Transformation of Racemates and Total Spontaneous Resolution(p. 204)
• 7-3. Chemical Separation of Enantiomers via Diastereomers(p. 209)
• a. Formation and Separation of Diastereomers; Resolving Agents(p. 209)
• b. Resolution Principles and Practice(p. 227)
• c. Separation Via Complexes and Inclusion Compounds(p. 231)
• d. Chromatographic Resolution(p. 236)
• e. Asymmetric Transformations of Diastereomers(p. 240)
• f. General Methods for the Separation of Diastereomers(p. 246)
• 7-4. Enantiomeric Enrichment and Resolution Strategy(p. 253)
• 7-5. Kinetic Resolution(p. 257)
• a. Theory and Stoichiometric and Abiotic Catalytic Kinetic Resolution(p. 258)
• b. Enzymatic Resolution(p. 268)
• 7-6. Miscellaneous Separation Methods(p. 274)
• 7-7. Racemization(p. 277)
• a. Racemization Processes(p. 278)
• b. Racemization of Amino Acids(p. 284)
• References(p. 287)
• 8 Heterotopic Ligands and Faces: Prostereoisomerism and Prochirality(p. 303)
• 8-1. Introduction and Terminology(p. 303)
• 8-2. Significance and History(p. 305)
• 8-3. Homotopic and Heterotopic Ligands and Faces(p. 307)
• a. Homotopic Ligands and Faces(p. 307)
• b. Enantiotopic Ligands and Faces(p. 310)
• c. Diastereotopic Ligands and Faces(p. 312)
• d. Concepts and Nomenclature(p. 315)
• 8-4. Heterotopicity and Nuclear Magnetic Resonance(p. 318)
• a. General Principles. Anisochrony(p. 318)
• b. NMR in Assignment of Configuration and of Descriptors of Prostereoisomerism(p. 320)
• c. Origin of Anisochrony(p. 323)
• d. Conformationally Mobile Systems(p. 325)
• 8-5. Heterotopic Ligands and Faces in Enzyme-Catalyzed Reactions(p. 329)
• a. Heterotopicity and Stereoelective Synthesis(p. 329)
• b. Heterotopicity and Enzyme-Catalyzed Reactions(p. 330)
• References(p. 335)
• 9 Stereochemistry of Alkenes(p. 339)
• 9-1. Structure of Alkenes and Nature of cis-trans Isomerism(p. 339)
• a. General(p. 339)
• b. Nomenclature(p. 340)
• c. Cumulenes(p. 342)
• d. Alkenes with Low Rotational Barriers and Nonplanar Alkenes(p. 342)
• e. The C=N and N=N Double Bonds(p. 346)
• 9-2. Determination of Configuration of cis-trans Isomers(p. 348)
• a. Chemical Methods(p. 348)
• b. Physical Methods(p. 353)
• 9-3. Interconversion of cis-trans Isomers: Position of Equilibrium and Methods of Isomerization(p. 362)
• a. Position of cis-trans Equilibria(p. 362)
• b. Methods of Equilibration(p. 366)
• c. Directed cis-trans Interconversion(p. 368)
• References(p. 371)
• 10 Conformation of Acyclic Molecules(p. 376)
• 10-1. Conformation of Ethane, Butane, and Other Simple Saturated Acyclic Molecules(p. 376)
• a. Alkanes(p. 376)
• b. Saturated Acyclic Molecules with Polar Substituents or Chains and the Anomeric Effect(p. 383)
• 10-2. Conformation of Unsaturated Acyclic and Miscellaneous Compounds(p. 388)
• a. Unsaturated Acyclic Compounds(p. 388)
• b. Alkylbenzenes(p. 395)
• c. Miscellaneous Compounds(p. 397)
• 10-3. Physical and Spectral Properties of Diastereomers and Conformers(p. 398)
• a. General(p. 398)
• b. Dipole Moments(p. 399)
• c. Infrared Spectra(p. 400)
• d. NMR Spectroscopy(p. 401)
• 10-4. Conformation and Reactivity: The Winstein-Holness Equation and the Curtin-Hammett Principle(p. 407)
• References(p. 415)
• 11 Configuration and Conformation of Cyclic Molecules(p. 421)
• 11-1. Stereoisomerism and Configurational Nomenclature of Ring Compounds(p. 421)
• 11-2. Determination of Configuration of Substituted Ring Compounds(p. 423)
• a. Introduction(p. 423)
• b. Symmetry-Based Methods(p. 424)
• c. Methods Based on Physical and Chemical Properties(p. 425)
• d. Correlation Methods(p. 427)
• 11-3. Stability of Cyclic Molecules(p. 429)
• a. Strain(p. 429)
• b. Ease of Cyclization as a Function of Ring Size(p. 432)
• c. Ease of Ring Closure as a Function of the Ring Atoms and Substitutents: The Thorpe-Ingold Effect(p. 433)
• d. Baldwin's Rules(p. 434)
• 11-4. Conformational Aspects of the Chemistry of Six-Membered Ring Compounds(p. 436)
• a. Cyclohexane(p. 436)
• b. Monosubstituted Cyclohexanes(p. 439)
• c. Disubstituted and Polysubstituted Cyclohexanes(p. 447)
• d. Conformation and Physical Properties in Cyclohexane Derivatives(p. 453)
• e. Conformation and Reactivity in Cyclohexanes(p. 457)
• f. sp[superscript 2] Hybridized Cyclohexyl Systems(p. 463)
• g. Six-Membered Saturated Heterocycles(p. 472)
• 11-5. Chemistry of Ring Compounds Other than Six-Membered Ones(p. 480)
• a. Three-Membered Rings(p. 480)
• b. Four-Membered Rings(p. 481)
• c. Five-Membered Rings(p. 482)
• d. Rings Larger Than Six-Membered(p. 485)
• 11-6. Stereochemistry of Fused, Bridged, and Caged Ring Systems(p. 491)
• a. Fused Rings(p. 492)
• b. Bridged Rings(p. 501)
• c. Propellanes(p. 505)
• d. Catenanes, Rotaxanes, Knots, and Mobius Strips(p. 505)
• e. Cubane, Tetrahedrane, Dodecahedrane, Adamantane, and Buckminsterfullerene(p. 513)
• References(p. 517)
• 12 Chiroptical Properties(p. 534)
• 12-1. Introduction(p. 534)
• 12-2. Optical Activity and Anisotropic Refraction(p. 535)
• a. Origin and Theory(p. 535)
• b. Optical Rotatory Dispersion(p. 541)
• 12-3. Circular Dichroism and Anisotropic Absorption(p. 544)
• 12-4. Applications of Optical Rotary Dispersion and Circular Dichroism(p. 548)
• a. Determination of Configuration and Conformation: Theory(p. 548)
• b. Classification of Chromophores(p. 550)
• c. Sector and Helicity Rules(p. 553)
• d. Exciton Chirality(p. 567)
• e. Other Applications: Induced ORD and CD(p. 570)
• f. Circular Dichroism of Chiral Polymers(p. 576)
• 12-5. Applications of Optical Activity(p. 585)
• a. Polarimetry(p. 585)
• b. Empirical Rules and Correlations: Calculation of Optical Rotation(p. 593)
• 12-6. Vibrational Optical Activity(p. 597)
• References(p. 598)
• 13 Chirality in Molecules Devoid of Chiral Centers(p. 608)
• 13-1. Introduction and Nomenclature(p. 608)
• 13-2. Allenes(p. 611)
• a. Historical Overview and Natural Occurrence(p. 611)
• b. Synthesis of Optically Active Allenes(p. 612)
• c. Determination of Configuration and Enantiomeric Purity of Allenes(p. 613)
• d. Cyclic Allenes, Cumulenes, and Ketene Imines(p. 616)
• 13.3. Alkylidenecycloalkanes(p. 617)
• 13-4. Spiranes(p. 620)
• 13-5. Biphenyls and Atropisomerism(p. 622)
• a. Introduction(p. 622)
• b. Biphenyls and Other Atropisomers of the sp[superscript 2]-sp[superscript 2] Single-Bond Type(p. 623)
• c. Atropisomerism About sp[superscript 2]-sp[superscript 3] Single Bonds(p. 629)
• d. Atropisomerism About sp[superscript 3]-sp[superscript 3] Bonds(p. 630)
• 13-6. Molecular Propellers(p. 632)
• 13-7. Helicenes(p. 636)
• 13-8. Molecules with Planar Chirality(p. 638)
• a. Introduction(p. 638)
• b. Cyclophanes(p. 639)
• c. trans-Cycloalkenes(p. 640)
• d. Metallocenes and Related Compounds(p. 642)
• References(p. 642)
• Index(p. 649)

Notas de autor provistas por Syndetics

ERNEST L. ELIEL, PhD, is W. R. Kenan Jr. Professor Emeritus at the University of North Carolina, Chapel Hill, North Carolina. He is the coauthor of Stereochemistry of Organic Compounds and the recipient of numerous academic and scientific awards. Professor Eliel is past president of the American Chemical Society and a member of the National Academy of Sciences.

SAMUEL H. WILEN, PhD, (deceased) was Professor of Chemistry at City College, City University of New York.

MICHAEL P. DOYLE, PhD, is Vice President of Research Corporation, located in Tucson, Arizona, and Professor of Chemistry at the University of Arizona. He is the recipient of numerous awards for research and teaching.