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

Reddy, J. Prakasha; Steed, Jonathan W.

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


J. Prakasha Reddy


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.


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.

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


Accepted Journal Article (810 Kb)

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

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