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Hypervalency in Organic Crystals: A Case Study of the Oxicam Sulfonamide Group

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† Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russian Federation
‡ Institute of Solid State Chemistry and Mechanochemistry SB RAS, Kutateladze 18, Novosibirsk 630128, Russian Federation
§ Scuola Superiore Normale, Piazza dei Cavalieri 7, Pisa 56126, Italy
*E-mail: [email protected]
Cite this: J. Phys. Chem. A 2016, 120, 51, 10289–10296
Publication Date (Web):December 8, 2016
https://doi.org/10.1021/acs.jpca.6b10703
Copyright © 2016 American Chemical Society
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    Abstract

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    The theoretical charge density of the active pharmaceutical ingredient piroxicam (PXM) was evaluated through density functional theory with a localized basis set. To understand the electronic nature of the sulfur atom within the sulfonamide group, a highly ubiquitous functional group in pharmaceutical molecules, a theoretical charge density study was performed on PXM within the framework of Bader theory. Focus is on developing a topological description of the sulfur atom and its bonds within the sulfonamide group. It was found that sulfur d-orbitals do not participate in bonding. Instead, the existence of a strongly polarized (“ionic”) bonding structure is found through a combined topological and natural bonding orbital analysis. This finding is in stark contrast to long-held theories of the bonding structure of organic sulfonamide and has important implications for the parametrization of calculations using classical approaches.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jpca.6b10703.

    • Illustrated test molecule, tabulated charge density and SF% values, tabulated SCF electronic energies, profiles of ellipticity, bond distances illustrated in sulfonamide group and associated VSCC with CPs of atoms bonded to S, tabulated NBO analysis (PDF)

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