Chapter 5. Electronic Effects of Cyano, Isocyano, Acetylenic and Diazonio Groups

  1. Professor Saul Patai
  1. John Shorter

Published Online: 29 JUL 2004

DOI: 10.1002/0470024771.ch5

Triple Bonded Functional Groups (1994)

Triple Bonded Functional Groups (1994)

How to Cite

Shorter, J. (1994) Electronic Effects of Cyano, Isocyano, Acetylenic and Diazonio Groups, in Triple Bonded Functional Groups (1994) (ed S. Patai), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470024771.ch5

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. School of Chemistry, University of Hull, Hull HU6 7RX, UK

Publication History

  1. Published Online: 29 JUL 2004
  2. Published Print: 31 OCT 1994

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Professor Saul Patai and
  2. Professor Zvi Rappoport

Series Editor Information

  1. The Hebrew University, Jerusalem, Israel

ISBN Information

Print ISBN: 9780471935599

Online ISBN: 9780470024775

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Summary

This chapter contains sections titled:

  • Introduction

    • The Scope of this Chapter

    • Historical Introduction

  • The Hammett Equation

    • Introduction

    • Multiparameter Extensions

  • Electronic Effects of CN on the Strengths of Carboxylic and Other Acids

    • Alicyclic and Aliphatic Systems

    • Aromatic Systems

    • Acids of the Type Ph[BOND]G[BOND]COOH

    • Phenol and Anilinium Ion

  • The Ortho-effect of CN

    • Introduction

    • Ionization of Carboxylic and Other Acids

    • The Reactions of Ortho-substituted Benzoic Acids with Diazodiphenylmethane (DDM)

  • Substituent Constants of CN from the Application of Modern Experimental and Theoretical Techniques

    • Experimental Techniques

    • Theoretical Techniques

  • Electronic Effects of CN on Various Systems and Processes

    • Formation and Stabilization of Carbanions

      • Introduction

      • Equilibrium Acidities of Cyanocarbon Acids

      • Kinetic Acidities of Cyanocarbon Acids

      • Correlation Analysis of C[BOND]H Acidity and the Origin of the Stabilization of Carbanions by CN

    • Nucleophilic Substitution

    • Electrophilic Aromatic Substitution

    • Liquid Crystals

  • Substituent Constants of CN and of Groups Containing It: Recapitulation and Some Extension

    • Introduction

    • Recapitulation

    • The Effects of Substituents Containing CN

  • Electronic Effects of NC, the Isocyano Group

  • Electronic Effects of the Unipole N2+

    • Introduction

    • The Behaviour of Unipolar Substituents with Respect to the Hammett Equation

    • Wepster's Treatment of Unipolar Substituents

  • The Electronic Effects of Acetylenic Groups

    • The Characteristics of the Ethynyl Group

    • Structural Effects in Aliphatic Acids Containing C[TRIPLE BOND]C

    • The Transmission of Substituent Effects through C[TRIPLE BOND]C

  • Some Further Multiparameter Treatments of Substituent Effects

    • Introduction

    • Exner's Analysis

    • C. G. Swain's Treatments

    • The Poly Substituent-parameter (PSP) Equation

    • Charton's LDR Equation

  • References and Notes