Effects of Medium and Substituents on Dissociationof 4,4'-Disubstituted Bis(benzenesulfon)imides

[img]PDF - Authorized users only
Language: English
56Kb
Title:Effects of Medium and Substituents on Dissociationof 4,4'-Disubstituted Bis(benzenesulfon)imides
Creators:
Ludwig, Miroslav
Štverka, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 8, pp. 1205-1214
Uncontrolled Keywords:Chemometrics, Solvent, Substituent, Dissociation, Sulfonamides

Abstract

Ten 4,4'-disubstituted bis(arenesulfon)imides of the general formula XC<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>NHSO<sub>2</sub>C<sub>6</sub>H<sub>4</sub>X have been synthesized and their structures confirmed by their <sup>1</sup>H NMR spectra. Elemental analyses are presented for the compounds not yet described. The dissociation constants of these model substances have been measured potentiometrically in pyridine, dimethylformamide, methanol, ethanol, propylene carbonate, acetone, acetonitrile, 1,2-dichloroethane and tetramethylene sulfone. The p<i>K</i><sub>HA </sub>values obtained have been correlated with three sets of the Hammett substituent constants and the results have been used to discuss the solvent and substituent effects on the dissociation of the compounds studied. Sulfonimides with electron-acceptor substituents behave as rather strong acids in some solvents (pyridine, dimethylformamide, methanol and ethanol), whereas normal substituent dependences are found in other solvents. The experimental data have also been interpreted with the help of the statistical methods based on latent variables. From the calculations it follows that only the first principal component, which correlates well with the substituent constant sets adopted, is statistically significant in describing the substituent effect on the acid-base process studied.

Title:Effects of Medium and Substituents on Dissociationof 4,4'-Disubstituted Bis(benzenesulfon)imides
Creators:
Ludwig, Miroslav
Štverka, Pavel
Uncontrolled Keywords:Chemometrics, Solvent, Substituent, Dissociation, Sulfonamides
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:61
Number:8
Page Range:pp. 1205-1214
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19961205UNSPECIFIED
ID Code:1025
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:06

Citation

Ludwig, Miroslav; Štverka, Pavel (1996) Effects of Medium and Substituents on Dissociationof 4,4'-Disubstituted Bis(benzenesulfon)imides. Collection of Czechoslovak Chemical Communications, 61 (8). pp. 1205-1214. ISSN 0010-0765

Repository Staff Only: item control page