"Conformational simulation" of sulfamethizole by molecular complexation and insights from charge density analysis: Role of intramolecular S···O chalcogen bonding

Sajesh Thomas, S.P.K.P. Veccham, L.J. Farrugia, T.N.G. Row

Research output: Contribution to journalArticlepeer-review

45 Citations (Scopus)

Abstract

© 2015 American Chemical Society. Intramolecular S···O chalcogen bonding and its potential to lock molecular conformation have been examined in the crystal forms of sulfamethizole, a sulfonamide antibiotic. Molecular complexes of sulfamethizole, including salts and cocrystal, have been synthesized, and their crystal structures were analyzed in order to examine the possible conformational preferences of the molecule in various ionic states and supramolecular environments (neutral/cocrystal, anionic salt, and cationic salt forms). The electrostatic potential mapped on Hirshfeld surfaces generated for these crystal forms provides insights into the possible binding modes of the drug in different environments. Further, the observed conformation locking feature has been rationalized in terms of the experimental charge density features of the intramolecular S···O chalcogen bonding in sulfamethizole. The study quantitatively illustrates and rationalizes an intriguing case of a local minimum of molecular conformation being exclusively preferred over the global minimum, as it facilitates more efficient intermolecular interactions in a supramolecular environment.
Original languageEnglish
Pages (from-to)2110-2118
JournalCrystal Growth and Design
Volume15
Issue number5
DOIs
Publication statusPublished - 2015

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