Martin, Adam D., Britton, Joshua, Easun, Timothy  ORCID: https://orcid.org/0000-0002-0713-2642, 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: | 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: | 05 May 2023 07:51 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/74096 |
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