Issue 20, 2014
From the journal:

CrystEngComm

Competition and cooperation: hydrogen and halogen bonding in co-crystals involving 4-iodotetrafluorobenzoic acid, 4-iodotetrafluorophenol and 4-bromotetrafluorophenol†‡

Akihiro Takemura,a   Linda J. McAllister,a   Peter B. Karadakov,a   Natalie E. Pridmore,a   Adrian C. Whitwooda  and  Duncan W. Bruce*a  

* Corresponding authors

a Department of Chemistry, University of York, Heslington, YORK YO10 5DD, UK
E-mail: duncan.bruce@york.ac.uk
Tel: (+44) (0)1904 324085

Abstract

Co-crystallisation of 4-iodotetrafluorobenzoic acid with 1,4-dithiane leads to a polymer in which the benzoic acid dimer remains intact, forming halogen bonds with the dithiane, showing that considering both pKb and the iodine basicity scale (pKBI2) can direct the structure formed. Crystallisation of 4-halotetrafluorophenols with 1,4-dithiane or tetrahydrothiophene was always accompanied by oxidation to the S-oxide or S,S′-dioxide and in two cases the co-crystals formed involved hydrogen bonding (4-bromotetrafluorophenol) and both hydrogen and halogen bonding (4-iodotetrafluorophenol). Co-crystallisation of 4-iodotetrafluorophenol with 4,4′-bipyridine leads to a linear polymer with both hydrogen and halogen bonding.

Graphical abstract: Competition and cooperation: hydrogen and halogen bonding in co-crystals involving 4-iodotetrafluorobenzoic acid, 4-iodotetrafluorophenol and 4-bromotetrafluorophenol

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Article information

DOI
https://doi.org/10.1039/C4CE00319E
Article type
Paper
Submitted
13 Feb 2014
Accepted
27 Mar 2014
First published
09 Apr 2014

CrystEngComm, 2014,16, 4254-4264

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Competition and cooperation: hydrogen and halogen bonding in co-crystals involving 4-iodotetrafluorobenzoic acid, 4-iodotetrafluorophenol and 4-bromotetrafluorophenol

A. Takemura, L. J. McAllister, P. B. Karadakov, N. E. Pridmore, A. C. Whitwood and D. W. Bruce, CrystEngComm, 2014, 16, 4254 DOI: 10.1039/C4CE00319E

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