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

doi:10.1039/c4ce00319e

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 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 language	English
Pages (from-to)	4254-4264
Number of pages	11
Journal	CrystEngComm
Volume	16
Issue number	20
DOIs	https://doi.org/10.1039/c4ce00319e
Publication status	Published - 28 May 2014

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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 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",

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AU - Takemura, A.

AU - McAllister, L.J.

AU - Karadakov, P.B.

AU - Pridmore, N.E.

AU - Whitwood, A.C.

AU - Bruce, D.W.

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AB - 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

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

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