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Issue 18, 2013
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4-Bromo-trans-cinnamic acid: structural characterisation and crystallographic investigation into the solid state [2 + 2] cycloaddition reaction and temperature induced phase transition

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Abstract

4-Bromo-trans-cinnamic acid (1) displays some interesting behaviour in the solid-state undergoing a photo-induced head-to-head [2 + 2] cycloaddition reaction in addition to a reversible phase transition. Differential scanning calorimetry established that the thermal phase transition shows a slight hysteresis occurring at 252 K upon cooling and 256 K upon warming. Interestingly it was noted that upon photoirradiation above the phase transition temperature the compound appears to undergo a conversion to the low temperature form, prior to undergoing a cycloaddition reaction. Crystal structures of 1 were determined at 120, 240 and 300 K and found to be in the monoclinic space group P21/n at all three temperatures. The crystal structure of 1i was obtained, after recrystallisation of a powdered sample of 1 that had been irradiated at room temperature, and was found to be in the triclinic space group P[1 with combining macron]. In all cases, the structures were found to be stabilised by the presence of O–H⋯O hydrogen bonding and C–H⋯O interactions. The results of these investigations are presented herein.

Graphical abstract: 4-Bromo-trans-cinnamic acid: structural characterisation and crystallographic investigation into the solid state [2 + 2] cycloaddition reaction and temperature induced phase transition

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Publication details

The article was received on 19 Feb 2013, accepted on 08 Mar 2013 and first published on 25 Mar 2013


Article type: Paper
DOI: 10.1039/C3CE40300A
CrystEngComm, 2013,15, 3547-3553

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    4-Bromo-trans-cinnamic acid: structural characterisation and crystallographic investigation into the solid state [2 + 2] cycloaddition reaction and temperature induced phase transition

    J. L. R. Yates and H. A. Sparkes, CrystEngComm, 2013, 15, 3547
    DOI: 10.1039/C3CE40300A

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