Intramolecular Nonbonded S...N Interaction in Rabeprazole
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- Hayashi Kazuhiko
- College of Pharmacy, Kinjo Gakuin University
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- Ogawa Shiho
- Graduate School of Pharmaceutical Sciences, The University of Tokushima
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- Sano Shigeki
- Graduate School of Pharmaceutical Sciences, The University of Tokushima
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- Shiro Motoo
- Rigaku Corporation
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- Yamaguchi Kentaro
- Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunnri University
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- Sei Yoshihisa
- Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunnri University
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- Nagao Yoshimitsu
- Graduate School of Pharmaceutical Sciences, The University of Tokushima
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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).
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 56 (6), 802-806, 2008
The Pharmaceutical Society of Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390001204170061568
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- NII Article ID
- 110006684278
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 9508690
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed
