Hayashi K, Ogawa S, Sano S, Shiro M, Yamaguchi K, Sei Y, Nagao Y
Intramolecular Nonbonded S...N Interaction in Rabeprazole. [JOURNAL ARTICLE]
Chem Pharm Bull (Tokyo) 2008; 56(6):802-806.
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).
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