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The Weak Hydrogen BondIn Structural Chemistry and Biology$
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Gautam Desiraju and Thomas Steiner

Print publication date: 2001

Print ISBN-13: 9780198509707

Published to Oxford Scholarship Online: January 2010

DOI: 10.1093/acprof:oso/9780198509707.001.0001

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Other weak and non-conventional hydrogen bonds

Other weak and non-conventional hydrogen bonds

Chapter:
(p.122) 3 Other weak and non-conventional hydrogen bonds
Source:
The Weak Hydrogen Bond
Author(s):

GAUTAM R. DESIRAJU

THOMAS STEINER

Publisher:
Oxford University Press
DOI:10.1093/acprof:oso/9780198509707.003.0003

The C-H···O hydrogen bond is considered the archetypical weak hydrogen bond. Donors and acceptors in weak and non-conventional hydrogen bonds encompass wide ranges of acidity and basicity and of hardness and softness. In this sense, the C-H···O bond, with its weak acid-strong base and soft acid-hard base combination, exemplifies but only a small region of the overall domain of weak hydrogen bonding. This chapter examines a much larger variety of weak hydrogen bonds. Systematic variations of the donor and acceptor moieties are first discussed, focusing on the important aromatic hydrogen bonds that are accepted by the faces of phenyl groups. The chapter then looks at other acceptors of variable efficacies as well as more exotic systems involving metal donors and acceptors, X-H groups of reverse polarisation, that is, with a negative charge on the H atom. Some results of solution and gas phase experiments on simple systems are described, and examples of pi-acceptors, weak atomic acceptors, halide anions, weak donors, and organometallic complexes are considered.

Keywords:   donors, acceptors, phenyl groups, gas phase experiments, halide anions, organometallic complexes

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