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, D.W. Bruce

Research output: Contribution to journalArticlepeer-review


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 pK and the iodine basicity scale (pK) 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
Issue number20
Publication statusPublished - 28 May 2014

Cite this