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An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols. [VIP paper]

An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols. [VIP paper]
An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols. [VIP paper]
Rewriting the rules as fluorination does not always increase hydrogen-bond acidity: while the strongly electron-withdrawing fluorine significantly enhances alcohol H-bond acidity in anti-vicinal fluorohydrins, an intramolecular F???HO interaction overrules completely the inductive effect. This leads to an overall decrease in alcohol H-bond acidity, compared to the corresponding nonfluorinated alcohol.
computational chemistry, conformation analysis, fluorine, fluorohydrins, hydrogen bonding
1433-7851
6176-6180
Graton, Jérôme
12432694-552e-4a40-9935-9ff7c77fbf07
Wang, Zhong
ef9f8b13-c3f0-48d7-b8e2-95b0f757c30a
Brossard, Anne-Marie
d2ee371c-ad70-4516-a055-1ad74cf535ec
Gonçalves Monteiro, Daniela
41a23a8e-bb6c-499f-b50d-dcada3362f5c
Le Questel, Jean-Yves
38aea4ae-64a3-43b7-8049-ea2f351459f2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Graton, Jérôme
12432694-552e-4a40-9935-9ff7c77fbf07
Wang, Zhong
ef9f8b13-c3f0-48d7-b8e2-95b0f757c30a
Brossard, Anne-Marie
d2ee371c-ad70-4516-a055-1ad74cf535ec
Gonçalves Monteiro, Daniela
41a23a8e-bb6c-499f-b50d-dcada3362f5c
Le Questel, Jean-Yves
38aea4ae-64a3-43b7-8049-ea2f351459f2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

Graton, Jérôme, Wang, Zhong, Brossard, Anne-Marie, Gonçalves Monteiro, Daniela, Le Questel, Jean-Yves and Linclau, Bruno (2012) An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols. [VIP paper]. Angewandte Chemie International Edition, 51 (25), 6176-6180. (doi:10.1002/anie.201202059).

Record type: Article

Abstract

Rewriting the rules as fluorination does not always increase hydrogen-bond acidity: while the strongly electron-withdrawing fluorine significantly enhances alcohol H-bond acidity in anti-vicinal fluorohydrins, an intramolecular F???HO interaction overrules completely the inductive effect. This leads to an overall decrease in alcohol H-bond acidity, compared to the corresponding nonfluorinated alcohol.

Text
An Unexpected and Significantly Lower Hydrogen-Bond-Donating Capacity of Fluorohydrins Compared to Nonfluorinated Alcohols - Graton - 2012 - Angewandte Chemie International Edition - Wiley Online Library.pdf - Version of Record
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e-pub ahead of print date: 10 May 2012
Published date: 18 June 2012
Keywords: computational chemistry, conformation analysis, fluorine, fluorohydrins, hydrogen bonding
Organisations: University of Southampton

Identifiers

Local EPrints ID: 340162
URI: http://eprints.soton.ac.uk/id/eprint/340162
ISSN: 1433-7851
PURE UUID: 8837f9c4-2a64-4fd7-bd7c-bf71db76b998
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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Date deposited: 13 Jun 2012 14:06
Last modified: 18 Feb 2021 16:55

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Contributors

Author: Jérôme Graton
Author: Zhong Wang
Author: Anne-Marie Brossard
Author: Daniela Gonçalves Monteiro
Author: Jean-Yves Le Questel
Author: Bruno Linclau ORCID iD

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