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

Thomas, S. P., Veccham, S. P. K. P., Farrugia, L. J. and Guru Row, T. N. (2015) “Conformational simulation” of sulfamethizole by molecular complexation and insights from charge density analysis: role of intramolecular S···O chalcogen bonding. Crystal Growth and Design, 15(5), pp. 2110-2118. (doi: 10.1021/cg5016687)

Abstract

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.

• Item Type: Articles
• Keywords: General materials science, general chemistry, condensed matter physics.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Farrugia, Dr Louis
• Authors: Thomas, S. P., Veccham, S. P. K. P., Farrugia, L. J., and Guru Row, T. N.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Crystal Growth and Design
• Publisher: American Chemical Society
• ISSN: 1528-7483
• ISSN (Online): 1528-7505
• Published Online: 15 April 2015