Acidity of arylsulfonamides as function of quantum chemical parameters of sulfonamide nitrogen
- Authors: Krylov E.N.1, Virzum L.V.2
-
Affiliations:
- Ivanovo State University
- Ivanovo State Agricultural Academy named D. K. Belyaev
- Issue: Vol 68, No 3 (2019)
- Pages: 527-531
- Section: Full Article
- URL: https://journals.rcsi.science/1066-5285/article/view/243310
- DOI: https://doi.org/10.1007/s11172-019-2449-8
- ID: 243310
Cite item
Abstract
The structures of aromatic sulfonamide molecules XPhSO2NH2 (X = H, 4-Me, 4-F, 4-Cl, 4-Br, 4-MeO, 4-OH, 4-NH2, 4-CN, 3-NO2, 4-NO2, 3,5-(NO2)2, 3,4-Cl2, 3-Cl-4-Me, 3,4-Me2, 3-Me-4-F, 2-Me) were calculated at the M06/6-311++G** (SMD) level of theory. The atomic electrostatic potentials (AEP) and the Hirshfeld charges of the sulfonamide nitrogen atoms were determined. Correlation equations relating the AEP to Bronsted acidities (pKa) of these compounds were obtained using published data and the previously unknown pKa values for a number of arylsulfonamides were calculated. These pKa values are consistent with independently determined free energies of acid dissociation of sulfonamides.
About the authors
E. N. Krylov
Ivanovo State University
Author for correspondence.
Email: enk2000S@yandex.ru
Russian Federation, 39 ul. Ermaka, Ivanovo, 153025
L. V. Virzum
Ivanovo State Agricultural Academy named D. K. Belyaev
Email: enk2000S@yandex.ru
Russian Federation, 45 ul. Sovetskaya, Ivanovo, 153012
Supplementary files
