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

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

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

22 Citations (Scopus)

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. This journal is

Original languageEnglish
Pages (from-to)4254-4264
Number of pages11
JournalCrystEngComm
Volume16
Issue number20
DOIs
Publication statusPublished - 28 May 2014

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