Structure-Acidity-IR Spectra Correlations for p-Substituted N-Phenylsulfonylbenzamides？ 英文参考文献.docVIP

Molecules 2004, 9, 213-222 molecules ISSN 1420-3049 Structure-Acidity-IR Spectra Correlations for p-Substituted N-Phenylsulfonylbenzamides? Alexander Perjessy and Zora Sustekova 1 , Walter M. F. Fabian 2,* , Patrik Parik 3 , Miroslav Ludwig 3 , Dusan Loos 1 1 1 Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina CH-2, SK - 842 15 Bratislava, Slovak Republic. Institute of Chemistry, Karl Franzens University, A - 8010 Graz, Austria. Department of Organic Chemistry, Faculty of Chemical Technology, University of Pardubice, CZ-532 10 Pardubice, Czech Republic. 2 3 ? This paper is dedicated in memoriam to our colleague Prof. Dr. Alexander Perjessy, who passed away on February 13, 2003, and who made so many invaluable contributions in the fields of IR spectroscopy and correlation analysis, especially spectra-structure-property relationships. * Author to whom correspondence should be addressed; e-mail: walter.fabian@uni-graz.at Received: 17 September 2003; in revised form: 12 February 2004 / Accepted: 8 March 2004 / Published: 31 March 2004 Abstract: The wavenumbers of the IR absorption bands of the C=O, S=O and N-H stretching vibrations for a series of p-substituted N-phenylsulfonylbenzamides were measured in trichloromethane. The bond orders, Mulliken charges, charge densities and heats of formation were calculated using the PM3 method. Fifty significant mutual mono parameter (MP) and six dual parameter (DP) correlations were found for the IR spectral, theoretical structural data, substituent constants and previously reported dissociation constants in five polar organic solvents. The transmission of the substituent effects has been discussed and the solvent effect on the slopes of some linear correlations was evaluated using different solvent parameters. The results showed that the factors describing the electronic s