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17 O NMR Spectroscopic Study of Tertiary Enaminones
Author(s) -
Zhuo JinCong
Publication year - 1996
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/(sici)1097-458x(199608)34:8<595::aid-omr941>3.0.co;2-o
Subject(s) - chemistry , chemical shift , carbon 13 nmr , carbon 13 nmr satellite , nmr spectra database , nuclear magnetic resonance spectroscopy , stereochemistry , fluorine 19 nmr , spectral line , polar , physics , astronomy
Natural abundance 17 O NMR spectra for 42 aliphatic and 13 cyclic enaminones with tertiary amino groups are reported. The 17 O NMR chemical shifts of enaminones depend upon the type, number and position of the substituents. Substituents at C‐1 cause shielding, and those at C‐2 or C‐3 cause deshielding. The 17 O NMR data of 4‐( N , N ‐dialkylamino)but‐3‐en‐2‐ones correlate well with the 1 H–C‐2 and the 13 C‐2 chemical shifts and with the p K a values of the corresponding dialkylamines. The 17 O NMR chemical shifts of enaminones are shifted to lower field in non‐polar solvents.