Intramolecular nonbonded S...N interaction in rabeprazole |
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Authors: | Hayashi Kazuhiko Ogawa Shiho Sano Shigeki Shiro Motoo Yamaguchi Kentaro Sei Yoshihisa Nagao Yoshimitsu |
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Affiliation: | College of Pharmacy, Kinjo Gakuin University, Nagoya, Japan. hayashi@kinjo-u.ac.jp |
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Abstract: | 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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