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13 C NMR chemical shift substituent effects. 5 —α‐Monosubstituted N,N ‐diethylacetamides
Author(s) -
Rittner Roberto,
Martins Marcos A. P.,
Clar Günter
Publication year - 1988
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.1260260116
Subject(s) - chemistry , chemical shift , electronegativity , steric effects , methylene , substituent , carbon 13 nmr , medicinal chemistry , alkyl , carbon fibers , stereochemistry , crystallography , organic chemistry , materials science , composite number , composite material
Carbon‐13 NMR chemical shifts of a series of α‐monosubstituted N,N ‐diethylacetamides [YCH 2 C(O)NEt 2 , Y = Me, Cl, Br, I, OMe, SMe, and NMe 2 ] are reported. The α‐methylene and carbonyl carbon chemical shifts are correlated with the Pauling electronegativities ( E p ) and Charton's localized electrical parameters (σ L ), respectively. The non‐equivalence of the chemical shifts for the syn and anti‐N ‐alkyl carbon atoms are attributed to the electric field and steric compression effects and also to the YCH 2 cis and trans ‐γ‐effects.