Intramolecular Nonbonded S···N Interaction in Rabeprazole

Kazuhiko Hayashi; Shiho Ogawa; Shigeki Sano; Motoo Shiro; Kentaro Yamaguchi; Yoshihisa Sei; Yoshimitsu Nagao

doi:10.1248/cpb.56.802

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Intramolecular Nonbonded S···N Interaction in Rabeprazole

Kazuhiko Hayashi, Shiho Ogawa, Shigeki Sano, Motoo Shiro, Kentaro Yamaguchi, Yoshihisa Sei, Yoshimitsu Nagao

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Keywords: nonbonded interaction, rabeprazole, X-ray crystallographic analysis, proton pump inhibitor, close contact

JOURNAL FREE ACCESS

2008 Volume 56 Issue 6 Pages 802-806

DOI https://doi.org/10.1248/cpb.56.802

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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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