Influence of fluorination on alcohol hydrogen-bond donating properties
Influence of fluorination on alcohol hydrogen-bond donating properties
Hydrogen bonding represents the most specific molecular interaction in biological recognition processes, and the controlled modulation of hydrogen bond properties of functional groups present in ligands is of great interest. The introduction of fluorine atoms in the vicinity of functional groups is one of the ways this can be achieved. In this chapter, a number of hydrogen bond acidity scales are reviewed, with a focus on the hydrogen bond donating capacity of alcohols. An overview of experimental data showing how the hydrogen bond donating capacity of alcohols is modulated by fluorination is given, followed by a rationalization of these results. Computational methodology to describe and predict hydrogen bonds is discussed, with a focus on a convenient method for accurate alcohol hydrogen bond donating capacity prediction.
Alcohol, Conformational analysis, electrostatic potential, fluorohydrin, hydrogen bond donating capacity
301-324
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Graton, Jérôme
12432694-552e-4a40-9935-9ff7c77fbf07
Le Questel, Jean-Yves
38aea4ae-64a3-43b7-8049-ea2f351459f2
2019
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Graton, Jérôme
12432694-552e-4a40-9935-9ff7c77fbf07
Le Questel, Jean-Yves
38aea4ae-64a3-43b7-8049-ea2f351459f2
Linclau, Bruno, Graton, Jérôme and Le Questel, Jean-Yves
(2019)
Influence of fluorination on alcohol hydrogen-bond donating properties.
In,
Haufe, Gunter and Leroux, Frederic R.
(eds.)
Fluorine in Life Sciences: Pharmaceuticals, Medicinal Diagnostics, and Agrochemicals: Progress in Fluorine Science.
Academic Press, .
(doi:10.1016/B978-0-12-812733-9.00008-8).
Record type:
Book Section
Abstract
Hydrogen bonding represents the most specific molecular interaction in biological recognition processes, and the controlled modulation of hydrogen bond properties of functional groups present in ligands is of great interest. The introduction of fluorine atoms in the vicinity of functional groups is one of the ways this can be achieved. In this chapter, a number of hydrogen bond acidity scales are reviewed, with a focus on the hydrogen bond donating capacity of alcohols. An overview of experimental data showing how the hydrogen bond donating capacity of alcohols is modulated by fluorination is given, followed by a rationalization of these results. Computational methodology to describe and predict hydrogen bonds is discussed, with a focus on a convenient method for accurate alcohol hydrogen bond donating capacity prediction.
Text
Linclau book chapter manuscript_revision_v3
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Accepted/In Press date: 19 June 2017
e-pub ahead of print date: 28 September 2018
Published date: 2019
Keywords:
Alcohol, Conformational analysis, electrostatic potential, fluorohydrin, hydrogen bond donating capacity
Identifiers
Local EPrints ID: 425308
URI: http://eprints.soton.ac.uk/id/eprint/425308
PURE UUID: 26f749a0-8aed-4f75-88f8-49aa3ddfbcc7
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Date deposited: 12 Oct 2018 16:30
Last modified: 16 Mar 2024 03:15
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Contributors
Author:
Jérôme Graton
Author:
Jean-Yves Le Questel
Editor:
Gunter Haufe
Editor:
Frederic R. Leroux
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