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Issue 13, 2012
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Pressure effects on H-ordering in hydrogen bonds and interactions in benzoic acid

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Abstract

High-pressure structures of benzoic acid, C6H5COOH, reveals the interplay of proton disorder in O–H⋯O hydrogen bonds, molecular orientation and O⋯O distance. The benzoic acid structures have been determined by single crystal X-ray diffraction up to 2.21 GPa at 296 K. The initial ordering of H atoms in the hydrogen bonds of benzoic acid dimers is reversed above 0.30 GPa. These opposite effects are due to the H-stabilization by enhanced interactions of the molecule in the asymmetric crystal environment, and to the compressed O⋯O distance, lowering the potential energy barrier for the H-hopping, respectively. Pressure facilitates the esterification of benzoic acid in methanol and ethanol solutions, but no symmetry, structure or crystal volume changes indicative of phase transition postulated for this compound have been observed.

Graphical abstract: Pressure effects on H-ordering in hydrogen bonds and interactions in benzoic acid

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Publication details

The article was received on 27 Jan 2012, accepted on 18 Apr 2012 and first published on 22 May 2012


Article type: Paper
DOI: 10.1039/C2CE25128K
Citation: CrystEngComm, 2012,14, 4420-4424
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    Pressure effects on H-ordering in hydrogen bonds and interactions in benzoic acid

    W. Cai and A. Katrusiak, CrystEngComm, 2012, 14, 4420
    DOI: 10.1039/C2CE25128K

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