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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: 27 June 2022

THE ROLE OF STRONG H-BONDS IN NATURE: A GALLERY OF FUNCTIONAL H-BONDS

THE ROLE OF STRONG H-BONDS IN NATURE: A GALLERY OF FUNCTIONAL H-BONDS

Chapter:
(p.245) 8 THE ROLE OF STRONG H-BONDS IN NATURE: A GALLERY OF FUNCTIONAL H-BONDS
Source:
The Nature of the Hydrogen Bond
Author(s):

Gastone Gilli

Paola Gilli

Publisher:
Oxford University Press
DOI:10.1093/acprof:oso/9780199558964.003.0009

Functional H-bonds are H-bonds which are significantly stronger than the surrounding ones and, for this reason, can play a specific role in the mechanism of action of important chemical or biochemical processes. This chapter reports a preliminary collection of these bonds organized in a graphic gallery of cases with little discussion, a collection of themes which have already been, or deserve to be, investigated to unravel the true role played by the H-bond in natural systems. Themes treated include: RAHB-driven processes (prototropic tautomerism in heteroconjugated systems, secondary structure of proteins, and DNA base pairing); H-bond-controlled crystal packing; bistable H-bonds in functional molecular materials (ferro/antiferroelectric crystals, excited-state proton transfer); low-barrier charge-assisted H-bonds in enzymatic catalysis (the catalytic triad of serine proteases; and proton transmission in water chains (Grotthuss mechanism, gramicidine A channel, aquaporin channels).

Keywords:   Functional H-bonds, prototropic tautomerism, α-helices, β-pleated sheets, DNA base pairing, crystal packing, ferroelectrics, ESIPT, serine proteases, ketosteroid isomerase

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