Polymorphism of (Z)-3-Bromopropenoic acid: a high and low Z' pair

Reddy, J. Prakasha; Steed, Jonathan W.

doi:10.1021/acs.cgd.6b00551

Polymorphism of (Z)-3-Bromopropenoic acid: a high and low Z' pair

Reddy, J. Prakasha; Steed, Jonathan W.

Authors

J. Prakasha Reddy

Professor Jonathan Steed jon.steed@durham.ac.uk
Professor

Abstract

Two polymorphic forms of (Z)-3-Bromopropenoic acid are reported. Form I (monoclinic, P21/c) with Z' = 1 is obtained from a range of solvents while Form II (monoclinic, P21/n) with Z' = 4 can be prepared only from either benzene or toluene. Both forms are isolated at room temperature. The molecules in both polymorphs interact with one another through similar dominant hydrogen bonding motifs; however, the packing arrangement differs in the prevalence of weaker hydrogen bonds in the metastable Form II. Analysis of this high and low Z′ polymorphic pair using differential scanning calorimetry, grinding and slurry experiments, coupled with lattice energy calculations suggests that the low Z′ form I is the most stable under ambient conditions. 2D fingerprint plots derived from Hirshfeld surfaces highlight the more extensive hydrogen bonding in Form II while Form I is more densely packed. This polymorphic pair mat be a candidate for the role of solution pre-aggregation in the formation of high Z′ forms.

Citation

Reddy, J. P., & Steed, J. W. (2016). Polymorphism of (Z)-3-Bromopropenoic acid: a high and low Z' pair. Crystal Growth and Design, 16, 4021-4025. https://doi.org/10.1021/acs.cgd.6b00551

Journal Article Type	Article
Acceptance Date	May 23, 2016
Online Publication Date	May 23, 2016
Publication Date	May 23, 2016
Deposit Date	May 31, 2016
Publicly Available Date	May 23, 2017
Journal	Crystal Growth and Design
Print ISSN	1528-7483
Electronic ISSN	1528-7505
Publisher	American Chemical Society
Peer Reviewed	Peer Reviewed
Volume	16
Pages	4021-4025
DOI	https://doi.org/10.1021/acs.cgd.6b00551

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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth & Design, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.cgd.6b00551.