Hypervalency in Organic Crystals: A Case Study of the Oxicam Sulfonamide Group Full article
Journal |
The Journal of Physical Chemistry A
ISSN: 1089-5639 , E-ISSN: 1520-5215 |
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Output data | Year: 2016, Volume: 120, Number: 51, Pages: 10289-10296 Pages count : 8 DOI: 10.1021/acs.jpca.6b10703 | ||||||
Tags | Active pharmaceutical ingredients Bonding structure Chemical equations Classical approach Electronic natures Natural bonding orbitals Parametrizations Topological description | ||||||
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Abstract:
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. (Chemical Equation Presented).
Cite:
Tantardini C.
, Boldyreva E.V.
, Benassi E.
Hypervalency in Organic Crystals: A Case Study of the Oxicam Sulfonamide Group
The Journal of Physical Chemistry A. 2016. V.120. N51. P.10289-10296. DOI: 10.1021/acs.jpca.6b10703 WOS Scopus РИНЦ
Hypervalency in Organic Crystals: A Case Study of the Oxicam Sulfonamide Group
The Journal of Physical Chemistry A. 2016. V.120. N51. P.10289-10296. DOI: 10.1021/acs.jpca.6b10703 WOS Scopus РИНЦ
Dates:
Submitted: | Oct 24, 2016 |
Accepted: | Dec 6, 2016 |
Published online: | Dec 16, 2016 |
Published print: | Dec 29, 2016 |
Identifiers:
Web of science | WOS:000391160200024 |
Scopus | 2-s2.0-85018944582 |
Elibrary | 31016605 |
Chemical Abstracts | 2016:2054352 |
Chemical Abstracts (print) | 166:65110 |
OpenAlex | W2560327832 |