A Study of Transmission Effects of Sulfonyl and Carbonyl Groups

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Title:A Study of Transmission Effects of Sulfonyl and Carbonyl Groups
Creators:
Ludwig, Miroslav
Pařík, Patrik
Kulhánek, Jiří
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 60, 5, pp. 841-850

Abstract

<p>Seventeen <i>p</i>-substituted <i>N</i>-phenylsulfonylbenzamides of general formulas XC<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>NHCOC<sub>6</sub>H<sub>5</sub> and C<sub>6</sub>H<sub>5</sub>SO<sub>2</sub>NHCOC<sub>6</sub>H<SUB >4</sub>X have been synthesized and their structure has been confirmed by elemental analysis and <sup>1</sup>H NMR spectra. The dissociation constants of all the compounds have been measured by potentiometric titration in methanol, acetonitrile, dimethylformamide, dimethyl sulfoxide, and pyridine. The obtained p<i>K</i><sub>HA</sub> values have been correlated with three sets of Hammett substituent constants using simple or double linear regression. The solvent and substituent effects are discussed on the basis of experimental results, and the difference between the substituent effects from sulfonamide and benzamide sections is evaluated. It has been found that due to the extensive delocalization of negative charge in the conjugated base the transmission effects of carbonyl and sulfonyl groups on the transmission of substituent effect are roughly the same. The experimental data have been interpreted by the methods with latent variables: the principal component analysis (PCA), the conjugated deviation analysis (CDA), and the method of projection to latent structures (PLS). The results obtained by these procedures were similar.

Title:A Study of Transmission Effects of Sulfonyl and Carbonyl Groups
Creators:
Ludwig, Miroslav
Pařík, Patrik
Kulhánek, Jiří
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:60
Number:5
Page Range:pp. 841-850
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19950841UNSPECIFIED
ID Code:774
Item Type:Article
Deposited On:06 Feb 2009 17:03
Last Modified:06 Feb 2009 16:03

Citation

Ludwig, Miroslav; Pařík, Patrik; Kulhánek, Jiří (1995) A Study of Transmission Effects of Sulfonyl and Carbonyl Groups. Collection of Czechoslovak Chemical Communications, 60 (5). pp. 841-850. ISSN 0010-0765

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