Chapter 1. Some Intrinsic Features of Hydroxylamines, Oximes and Hydroxamic Acids: Integration of Theory and Experiment

  1. Professor Zvi Rappoport3 and
  2. Joel F. Liebman4
  1. Peter Politzer1,2 and
  2. Jane S. Murray1,2

Published Online: 19 DEC 2008

DOI: 10.1002/9780470741962.ch1

The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids

The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids

How to Cite

Politzer, P. and Murray, J. S. (2008) Some Intrinsic Features of Hydroxylamines, Oximes and Hydroxamic Acids: Integration of Theory and Experiment, in The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids (eds Z. Rappoport and J. F. Liebman), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/9780470741962.ch1

Editor Information

  1. 3

    The Hebrew University, Jerusalem, Israel

  2. 4

    Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, Maryland 21250, USA

Author Information

  1. 1

    Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA

  2. 2

    Department of Chemistry, Cleveland State University, Cleveland, OH 44115, USA

Publication History

  1. Published Online: 19 DEC 2008
  2. Published Print: 19 DEC 2008

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: 9780470512616

Online ISBN: 9780470741962

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Keywords:

  • hydroxylamine, oxime and hydroxamic acid features;
  • covalent and noncovalent interaction analysis;
  • lone pair–lone pair repulsion;
  • oxime isomerism;
  • hydroxylamine prototypical examples and comparisons;
  • hydrogen-bond donating and accepting possibilities;
  • global and local polarizability;
  • empirical hybrid atom and group polarizabilities

Summary

This chapter contains sections titled:

  • Introduction

  • Analysis of Covalent and Noncovalent Interactions

  • Computational Approach

  • Lone Pair-Lone Pair Repulsion

  • Comparison of Prototypical Examples

  • Oxime Isomerism

  • Hydrogen Bonding

  • Acidity/Basicity

  • Global and Local Polarizability

  • Conclusion

  • Acknowledgment

  • References