Dipole Moments in Organic Chemistry, Softcover reprint of the original 1st ed. 1970 Physical Methods in Organic Chemistry Series

In accordance with the aims of the series "Physical Methods in Organic Chemistry," of which this book forms part, the authors r main aim was a systematic account of the most important methods of using the method of dipole moments in organic chemistry and interpreting its results in practice. Since 1955, when two monographs devoted to the fundamentals and applications of the dipole moment method appeared simultaneously (C. P. Smyth, Dielectric Behavior and Structure, McGraw-Hill, New York; and J. W. Smith, Electric Dipole Moments, Butterworths, London), no generalizing studies of this type have appeared in the Russian and foreign literature. Nevertheless, it is just in this per­ iod that almost half of all publications on the structure and proper­ ties of organic compounds by means of the dipole moment method have appeared. During this time, the principles of the method of measure­ mentand the physical theory of the method have not undergone fundamental changes. Consequently, in giving an account of these matters we considered it sufficient to give a very short introduction to the theory of the method that is not burdened with details of the mathematical derivations and the strict formalism of the theory of dielectrics which are hardly used in the applications of the method that are of interest to the organiC chemist (Chapter I).

I Basic Principles of the Theory of Dielectrics.- 1. Behavior of a Dielectric in a Static Electric Field.- 2. Molecular Polarizability.- 3. Statistical Theory of the Polarization of Polar Liquid Dielectrics.- 4. Dielectric Properties of a Substance in a Variable Electric Field.- 5. Literature Cited.- II Nature of the Dipole Moment and Methods For Its Determination.- 1. Nature of the Dipole Moment.- 2. Methods of Determining Dipole Moments.- 3. Determination of the Dipole Moment in the Vapor Phase.- 4. Determination of the Dipole Moment in Dilute Solutions (Debye’s Second Method).- 5. Solvent Effect.- 6. Determination of the Dipole Moment by Means of the Stark Effect.- 7. Electric Resonance Method of Determining Dipole Moments.- 8. Determination of Dipole Moments of Liquids by Measuring Dielectric Losses in the Microwave Region.- 9. Literature Cited.- III Calculations in the Dipole Moment Method.- 1. Bond and Group Moments.- 2. Vectorial Additive Method for Calculating Dipole Moments of Molecules from Bond and Group Moments.- 3. Critical Observations on the Vectorial Additive Scheme and Methods for Its Improvement.- 4. Quantum-Mechanical Calculations of the Dipole Moments of Complex Molecules.- 5. Literature Cited.- IV Dipole Moments and the Stereochemistry of Organic Compounds.- 1. The Dipole Moment and the Symmetry of the Molecule.- 2. Geometrical cis-trans Isomerism Relative to Double Bonds.- 3. s-cis-trans Isomerism.- 4. Nonplanar Conformations of Aryl Nuclei in Uncondensed Aromatic Systems.- 5. Conformational Analysis of Saturated Cyclic Systems.- 6. Internal Rotation Relative to Single Bonds.- 7. Literature Cited.- V Dipole Moments and the Electronic Structure of Organic Compounds.- 1. Induction Effect.- 2. Conjugation of an Unsaturated System with Polar Groups.Mesomeric Moments. Interaction Moments.- 3. Dipole Moments and Intramolecular Polarization.- 4. Literature Cited.- VI Dipole Moments and Some Special Problems of the Structure and Properties of Organic Compounds.- 1. Tautomerism.- 2. The Hydrogen Bond.- 3. Intermolecular Interactions.- 4. Dipole Moments of Molecules in Electronically Excited States.- 5. Literature Cited.