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Hirshfeld surface investigation of structure-directing interactions within dipicolinic acid derivatives

Martin, Adam D., Britton, Joshua, Easun, Timothy, Blake, Alexander J., Lewis, William and Schröder, Martin 2015. Hirshfeld surface investigation of structure-directing interactions within dipicolinic acid derivatives. Crystal Growth and Design 15 (4) , pp. 1697-1706. 10.1021/cg5016934

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Abstract

Six compounds based on dipicolinic acid esters have been synthesized and Hirshfeld surfaces used to investigate the structure-directing effects of functional groups in controlling their solid-state behavior. Compounds 1–4 are 4-bromo dipicolinic acid esters substituted with methyl, ethyl, propyl, and benzyl groups, respectively. The main structure-directing motif within 1–3 is a pairwise O···H interaction involving two carbonyl oxygen atoms and two aromatic H atoms. The introduction of bulky benzyl groups in 4 forces a significant change in the position of this interaction. Compounds 2 and 4 were used in Suzuki coupling reactions to prepare extended analogues 5 and 6, respectively, and their solid-state behavior was also studied using Hirshfeld surfaces. Extension of these dipicolinic acid esters results in the complete loss of the pairwise O···H interaction in 5, where the dominant structure-directing motifs are π-based interactions. However, the pairwise O···H interaction reappears for the more flexible 6, demonstrating control of the solid-state structure of these dipicolinic acid derivatives through the choice of functional groups.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Additional Information: ACS AuthorChoice - This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes
Publisher: American Chemical Society
ISSN: 1528-7483
Date of First Compliant Deposit: 30 March 2016
Last Modified: 04 Jun 2017 08:12
URI: http://orca-mwe.cf.ac.uk/id/eprint/74096

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