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A 15 N nuclear magnetic resonance study of the base‐catalyzed NH 2 exchange reactions of acetamide and thioacetamide
Author(s) -
Nee Michael,
Chun Yu,
Squillacote Michael E.,
Roberts John D.
Publication year - 1982
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270180302
Subject(s) - acetamide , thioacetamide , amide , chemistry , catalysis , base (topology) , nuclear magnetic resonance , nuclear chemistry , organic chemistry , physics , biochemistry , mathematical analysis , mathematics
The base‐catalyzed NH 2 exchange reactions of acetamide and thioacetamide were studied by 15 N nuclear magnetic resonance spectroscopy by the use of line‐shape analysis. The 15 N NMR spectra of these primary amides at intermediate exchange rates were broad doublets, which indicated that the two amide protons were exchanging at different rates. The line‐shape analysis indicated that the ratio of exchange rates was 6±1 for acetamide and 3±1 for thioacetamide.