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
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
18 June 2012
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), .
(doi:10.1002/anie.201202059).
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
More information
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
Catalogue record
Date deposited: 13 Jun 2012 14:06
Last modified: 18 Feb 2021 16:55
Export record
Altmetrics
Contributors
Author:
Jérôme Graton
Author:
Zhong Wang
Author:
Anne-Marie Brossard
Author:
Daniela Gonçalves Monteiro
Author:
Jean-Yves Le Questel
University divisions
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics
