Chapter 8. Hydrogen-Bonded Complexes of Phenols

  1. Zvi Rappoport
  1. C. Laurence,
  2. M. Berthelot and
  3. J. Graton

Published Online: 7 OCT 2003

DOI: 10.1002/0470857277.ch8

Phenols

Phenols

How to Cite

Laurence, C., Berthelot, M. and Graton, J. (2003) Hydrogen-Bonded Complexes of Phenols, in Phenols (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470857277.ch8

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Laboratoire de Spectrochimie, University of Nantes, 2, rue de la Houssiniere BP 92208, F-44322 Nantes Cedex 3, France. Fax: (+33) (0)2 51 12 54 12

Publication History

  1. Published Online: 7 OCT 2003
  2. Published Print: 22 JUL 2003

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Zvi Rappoport

Series Editor Information

  1. The Hebrew University, Jerusalem, Israel

ISBN Information

Print ISBN: 9780471497370

Online ISBN: 9780470857274

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Summary

This chapter contains sections titled:

  • Introduction

  • Hydrogen-bond Basicity of Phenols

  • Hydrogen-bond Acidity of Phenols

    • equation image Scale

    • log Kα Scale

    • Complexation with Pyridine N-oxide

    • Solvatochromic Shifts of Reichardt's Betaine Dye

    • Hydrogen-bond Acidity from Partition Coefficients

  • Self-association of Phenols

  • Intramolecular Hydrogen Bonds

    • OH···O2N

    • OH···O[DOUBLE BOND]C

    • OH···Halogen

    • OH···OH(Me)

    • OH···N

  • Properties of the Complexes

    • Thermodynamic Properties

    • Binding Energy De and Dissociation Energy Do

    • Geometry of Phenol Hydrogen Bonds

    • Hydrogen-bonding Site(s)

  • Construction of Hydrogen-bond Basicity Scales from Phenols

    • Thermodynamic Scales of Hydrogen-bond Basicity

    • UV, NMR and IR Spectroscopic Scales

  • Hydrogen Bonding and Protonation

  • References