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Benzene dilution shifts and steric interactions in N , N ‐dialkylamides
Author(s) -
Graham Laurine L.,
Miller Michael R.
Publication year - 1972
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.1270040212
Subject(s) - benzene , steric effects , chemistry , dilution , chemical shift , amide , solvent , decoupling (probability) , carbon tetrachloride , medicinal chemistry , computational chemistry , stereochemistry , organic chemistry , physics , thermodynamics , control engineering , engineering
The NMR spectra of ten disubstituted amides have been recorded at 0°C in carbon tetrachloride and in benzene solutions. The benzene dilution shifts (ASIS) and proton spin decoupling were used to make the chemical shift assignments. A time‐averaged solvent cluster model for the association between the amide and benzene is consistent with the observed ASIS values. The assignments for the N ‐methine and N ‐methyl resonance peaks in RCON[CH(CH 3 ) 2 ] 2 , where R is methyl, ethyl or propyl are inverted from the assignments for N , N ‐diisopropylformamide (R H).