Issue 9, 2015

Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity

Abstract

The nucleophilic reactivity of fluoride ion is altered in the presence of hydrogen-bond donors, including alcohols. Relatively little is known about the coordination involved; to rectify this, the X-ray structures of fourteen novel fluoride–alcohol complexes with tetrabutylammonium as the counterion have been determined. The coordination number varies from two to four depending on the steric bulk of the alcohol and is closely linked to trends in reactivity. This diversity in coordination stoichiometry is unprecedented but significant, as it implies differences in the ability of the fluoride–alcohol complexes to dissociate in solution with release of a more active and/or selective fluoride source.

Graphical abstract: Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity

Supplementary files

Article information

Article type
Edge Article
Submitted
19 May 2015
Accepted
22 Jun 2015
First published
22 Jun 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2015,6, 5293-5302

Author version available

Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity

K. M. Engle, L. Pfeifer, G. W. Pidgeon, G. T. Giuffredi, A. L. Thompson, R. S. Paton, J. M. Brown and V. Gouverneur, Chem. Sci., 2015, 6, 5293 DOI: 10.1039/C5SC01812A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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