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The tautomerism of Omeprazole in solution: a 1H and 13C NMR study

✍ Scribed by Rosa M. Claramunt; Concepción López; Ibon Alkorta; José Elguero; Rong Yang; Steve Schulman

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
90 KB
Volume
42
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The tautomerism of 5(6)‐methoxy‐2‐{[(4‐methoxy‐3,5‐dimethyl‐2‐pyridinyl)methyl] sulfinyl}‐1__H__‐benzimidazole (omeprazole) was determined in solution, K~T~ = 0.59 in THF at 195 K, in favor of the 6‐methoxy tautomer. The assignment of the signals was made by comparison with its two N‐methyl derivatives in acetone‐d~6~ and through theoretical calculations of the absolute shieldings (GIAO/DFT/6‐311++G**). Copyright © 2004 John Wiley & Sons, Ltd.

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