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15 N NMR: Iminothiol‐thioamide tautomerism of 2‐mercaptobenzazoles and 1‐methyl‐2‐mercaptoimidazole
Author(s) -
Balestrero R. S.,
Forkey D. M.,
Russell J. G.
Publication year - 1986
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.1260240803
Subject(s) - thioamide , tautomer , chemistry , chemical shift , nitrogen , nitrogen atom , nmr spectra database , carbon 13 nmr , medicinal chemistry , atom (system on chip) , stereochemistry , computational chemistry , spectral line , organic chemistry , ring (chemistry) , physics , astronomy , computer science , embedded system
15 N NMR spectra of a number of 2‐mercaptoazoles were obtained and the position of the iminothiol‐thioamide prototropic tautomeric equilibrium was determined. Because of the large chemical shift difference of ca 100 ppm between the iminothiol and thioamide nitrogen atoms, the 15 N chemical shifts of the S ‐methyl and N ‐methyl analogs of each tautomer provided reasonable chemical shift models for the same nitrogen atom in the tautomers. Only a small correction for an N ‐methyl effect was required.