sulfenamide and pyridine

Intramolecular nonbonded S...N interactions in the crystal structures of the derivatives (7a-d) of sodium rabeprazole (1) and an intermolecular nonbonded S...N interaction between ethylmethylsulfoxide and pyridine in a solution were recognized. These results made us estimate that the intramolecular nonbonded S...N interaction existed in 1 and its derivatives in a solution, and formed the 4-membered quasi-ring in 2 (Fig. 1) followed by the increase of the reactivity of 2 to give the putative spiro sulfoxide 3, which is the key intermediate in the reaction cascade of 1 (Chart 1).

Topics: 2-Pyridinylmethylsulfinylbenzimidazoles; Crystallography, X-Ray; Cysteine; Indicators and Reagents; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular Conformation; Proton Pump Inhibitors; Pyridines; Rabeprazole; Solutions; Spectrometry, Mass, Electrospray Ionization; Spectrometry, Mass, Fast Atom Bombardment; Spectroscopy, Fourier Transform Infrared; Sulfamerazine