Structure-Acidity-IR Spectra Correlations for p-Substituted N-Phenylsulfonylbenzamides†

Molecules

Alexander Perjessy²  Walter M. F. Fabian³  Patrik Parik¹  Miroslav Ludwig¹  Dusan Loos² 

[1] Department of Organic Chemistry, Faculty of Chemical Technology, University of Pardubice, CZ‑532 10 Pardubice, Czech Republic.;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.

关键词: Substituted N-phenylsulfonylbenzamides;    IR spectral data;    PM3 calculations;    MP and DP correlations;    substituent and solvent effect;   

DOI  :  10.3390/90400213

来源: mdpi

【 摘 要 】

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 structure and controlling the dissociation equilibrium and the IR spectra properties of p-substituted N-phenylsulfonylbenzamides must be the same.

【 授权许可】

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