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The Nature of the Hydrogen BondOutline of a Comprehensive Hydrogen Bond Theory$
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Gastone Gilli and Paola Gilli

Print publication date: 2009

Print ISBN-13: 9780199558964

Published to Oxford Scholarship Online: September 2009

DOI: 10.1093/acprof:oso/9780199558964.001.0001

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PRINTED FROM OXFORD SCHOLARSHIP ONLINE (oxford.universitypressscholarship.com). (c) Copyright Oxford University Press, 2022. All Rights Reserved. An individual user may print out a PDF of a single chapter of a monograph in OSO for personal use.date: 05 July 2022

THE EMPIRICAL LAWS GOVERNING THE H-BOND: A SUMMARY

THE EMPIRICAL LAWS GOVERNING THE H-BOND: A SUMMARY

Chapter:
(p.193) 5 THE EMPIRICAL LAWS GOVERNING THE H-BOND: A SUMMARY
Source:
The Nature of the Hydrogen Bond
Author(s):

Gastone Gilli

Paola Gilli

Publisher:
Oxford University Press
DOI:10.1093/acprof:oso/9780199558964.003.0006

The analysis performed in Chapters 3 and 4 leads to formulate a number of rules which can be considered the empirical laws governing the H-bond. The first is that H-bonds are not an undifferentiated group but, conversely, need to be divided in classes according to their strength, mechanism of action, and modes of proton-exchange, acid-base association, and PA/pKa matching, the most important subdivision remaining that in six chemical leitmotifs (CLs), four of which collect all strong H-bonds known in nature. It is eventually concluded that the H-bond behaves as an interaction having a twofold nature (electrostatic and covalent) and a dual logic (two bonds formed by a same proton with two lone-pair donors) which, for these very reasons, is fully interpreted and rationalized in terms of VB theory (the electrostatic-covalent H-bond model) or general acid-base theory (the PA/pKa equalization principle).

Keywords:   empirical H-bond laws, H-bond classifications, chemical leitmotifs, twofold nature, dual logic, ECHBM, PA/pKa equalization

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