Acidity of arylsulfonamides as function of quantum chemical parameters of sulfonamide nitrogen


Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

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

Supplementary Files
Action
1. JATS XML

Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature