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NMR study of the synthesis of 17 O‐enriched acetic acid by hydrolysis of acetic anhydride with 17 O‐enriched water
Author(s) -
Hultman Heidi M.,
Djanashvili Kristina,
Peters Joop A.
Publication year - 2003
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1266
Subject(s) - chemistry , acetic anhydride , acetic acid , hydrolysis , hydroxyl value , pummerer rearrangement , nucleophile , ether , nuclear magnetic resonance spectroscopy , organic chemistry , medicinal chemistry , catalysis , polyol , polyurethane
17 O‐enriched acetic acid (2.5% in 17 O) was synthesized by hydrolysis of acetic anhydride with 17 O‐enriched water. The reaction was monitored by 17 O and 1 H NMR spectroscopy. Acetic anhydride, 17 O‐enriched in both the ether and the carbonyl oxygens, was observed as an intermediate. This can be ascribed to competition between acetic acid and water for nucleophilic attack on acetic anhydride. Copyright © 2003 John Wiley & Sons, Ltd.