title: 2-Benzyl-2-methyl-2H-benzimidazole 1,3-dioxide derivatives: Spectroscopic and theoretical study.
abstract: The spectroscopic behavior of 2-benzyl-2-methyl-2H-benzimidazole 1,3-dioxide derivatives in solution was studied in terms of electronic and nuclear magnetic resonance ((1)H and (13)C NMR) techniques. The experimental spectra were compared to the theoretical ones, obtained at DFT level, proving that the compounds adopt in solution a bird-like conformational distribution. Also, theoretically this conformational distribution resulted the most stable in gas phase. Infrared spectroscopy was used to study solid state behavior identifying experimentally the N-O stretching near to 1380, 1365 and 1225 cm(-1) and the vibrational benzimidazole skeleton near to 1610 and 1590 cm(-1). The vibrational spectrum was satisfactorily described by DFT calculations funding the N-O stretching as a coupled vibration near to 1470, 1350 and 1285 cm(-1). The fragmentation that takes place in mass spectrometry was assigned for all of the new derivatives.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias-Facultad de Química, Universidad de la República, Iguá 4225, Montevideo 11400, Uruguay.
authors.forename: Alicia
authors.initials: A
authors.lastname: Merlino
authors.forename: Mariana
authors.initials: M
authors.lastname: Boiani
authors.forename: Hugo
authors.initials: H
authors.lastname: Cerecetto
authors.forename: Mercedes
authors.initials: M
authors.lastname: González
mesh_terms: D001562:Benzimidazoles; D003497:Cyclic N-Oxides; D009682:Magnetic Resonance Spectroscopy; D008432:Mathematical Computing; D008956:Models, Chemical; D012996:Solutions / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D014732:Vibration
chemical_list: D001562:Benzimidazoles; D003497:Cyclic N-Oxides; D012996:Solutions