Chapter 1. Enamines: General and Theoretical Aspects

  1. Zvi Rappoport Professor
  1. Günter Häfelinger1 and
  2. Hans-Georg Mack2

Published Online: 20 JUL 2004

DOI: 10.1002/0470024763.ch1

Enamines (1994)

Enamines (1994)

How to Cite

Häfelinger, G. and Mack, H.-G. (1994) Enamines: General and Theoretical Aspects, in Enamines (1994) (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470024763.ch1

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. 1

    Institute of Organic Chemistry, University of Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany

  2. 2

    Institute of Physical and Theoretical Chemistry, University of Tübingen, Auf der Morgenstelle 8, D-72076 Tübingen, Germany

Publication History

  1. Published Online: 20 JUL 2004
  2. Published Print: 31 AUG 1994

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Saul Patai and
  2. Zvi Rappoport

Series Editor Information

  1. The Hebrew University, Jerusalem, Israel

ISBN Information

Print ISBN: 9780471933397

Online ISBN: 9780470024768

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Summary

This chapter contains sections titled:

  • Introduction

    • Basic Definitions

    • Reviews

    • Classifications

      • Substitution at Nitrogen

        • Primary Enamines

        • Secondary Enamines

        • Tertiary Enamines

        • Heterosubstitution on Nitrogen

      • Substitution of the Ene Part

        • Acyclic Enamines

        • Endocyclic Enamines

        • Exocyclic Enamines

        • Heterocyclic Enamines

        • Bicyclic Enamines

    • Nomenclature

  • Molecular Geometries

    • Experimental Determinations of Molecular Structures

      • N-cyclic Tertiary Enamines

      • β-Enaminones

      • β-substituted and Miscellaneous Enamines

      • α-substituted Enamines

      • Summary of Experimentally Observed Variations in Molecular Structures of Enamines

    • Ab initio Calculations of Molecular Structures

      • Computational Methods

      • Notation for Gaussian-type Basis Functions

      • Vinylamine

        • Ground State Geometry

        • Torsion of the NH2 Group

        • Enamine–Imine Tautomerism: Z- and E-acetaldehyde Imine

        • N and C Protonation

      • α-substituted Vinylamines

      • E, Z-isomerism of β-substituted Vinylamines

      • N-substituted Vinylamines

        • N-Methyl Substituents

        • N-Fluoro Substituents

      • Citations of Special Calculations

        • Use of Semi-empirical Methods

        • Ab initio Calculations

  • Energetic Relations

    • Protonation Energies and Basicities of Enamines

    • Enthalpies of Formation and Hydrogenation

    • CC-tautomerism (Regioisomers)

  • Electronic Structure: Photoelectron Spectroscopy and MO Diagrams

    • Experimental Ionization Potentials

    • Ab initio Calculations of Molecular Orbital Energies

  • Dipole Moments and Conjugation

  • Spectroscopic Properties

    • Electron Spectroscopy

    • Infrared Spectroscopy

  • Acknowledgement

  • References