title: Structure-acidity-IR spectra correlations for p-substituted N-phenylsulfonylbenzamides.
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 structure and controlling the dissociation equilibrium and the IR spectra properties of p-substituted N-phenylsulfonylbenzamides must be the same.
authors.affiliation: Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina CH-2, SK - 842 15 Bratislava, Slovak Republic.
authors.forename: Alexander
authors.initials: A
authors.lastname: Perjessy
authors.forename: Walter M F
authors.initials: WM
authors.lastname: Fabian
authors.forename: Patrik
authors.initials: P
authors.lastname: Parik
authors.forename: Miroslav
authors.initials: M
authors.lastname: Ludwig
authors.forename: Dusan
authors.initials: D
authors.lastname: Loos
authors.forename: Zora
authors.initials: Z
authors.lastname: Sustekova
mesh_terms: D001549:Benzamides / Q000737:chemistry*; D002725:Chloroform / Q000737:chemistry; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013450:Sulfones / Q000737:chemistry*
chemical_list: D001549:Benzamides; D012997:Solvents; D013450:Sulfones; D002725:Chloroform