Hirshfeld Surface Investigation of Structure-Directing Interactions within Dipicolinic Acid Derivatives.

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 studie

SUBMITTER: Martin AD 

PROVIDER: S-EPMC4386464 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature