Using small molecule crystal structure data to obtain information about sulfonamide conformation

Parkin, A., Collins, A., Gilmore, C. J. and Wilson, C. C. (2008) Using small molecule crystal structure data to obtain information about sulfonamide conformation. Acta Crystallographica. Section B: Structural Science, 64(1), pp. 66-71. (doi: 10.1107/S0108768107065895)

Abstract

Understanding the conformations adopted by the sulfonamide group is essential to the understanding of the way that sulfa drugs act upon the body. The relative energies of these conformations in the solid state are estimated from the Cambridge Structural Database (CSD) using cluster analysis, and are used to confirm earlier findings that many high-level ab initio calculations do not reproduce the observed solid-state structure. These conformational studies have been extended to the adjacent torsion angles, and it has been shown that the sulfonamide group significantly affects the form adopted. The relative energies of the observed forms in the solid state have been estimated using data available in the CSD.

• Item Type: Articles
• Keywords: ab initio calculations AB-INITIO AB-INITIO CALCULATIONS AMIDES ANGLE CAMBRIDGE STRUCTURAL DATABASE CARBOXYLIC-ACIDS CLUSTER cluster analysis CLUSTER-ANALYSIS CONFORMATION CONFORMATIONS CRYSTAL Crystal structure CRYSTAL-STRUCTURE DATABASE DRUGS ENERGIES ENERGY FORCE-FIELD INFORMATION MOLECULE MOTIFS N-METHYLMETHANESULFONAMIDE SOLID-STATE STATE Structure
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Wilson, Professor Charles and Gilmore, Professor Chris and Collins, Miss Anna and Parkin, Dr Andrew
• Authors: Parkin, A., Collins, A., Gilmore, C. J., and Wilson, C. C.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Acta Crystallographica. Section B: Structural Science
• Publisher: Wiley-Blackwell Publishing, Inc.
• ISSN: 0108-7681
• ISSN (Online): 1600-5740