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

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

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 derivative...

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Veröffentlicht in:Magnetic resonance in chemistry 2004-08, Vol.42 (8), p.712-714
Hauptverfasser: Claramunt, Rosa M., López, Concepción, Alkorta, Ibon, Elguero, José, Yang, Rong, Schulman, Steve
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0749-1581
1097-458X
DOI:10.1002/mrc.1409