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17 O NMR and molecular mechanical studies of arylmethylenemalonaldehydes
Author(s) -
Kolehmainen Erkki,
Král Vladimir
Publication year - 1990
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.1260280904
Subject(s) - chemistry , chemical shift , nmr spectra database , coupling constant , carbon 13 nmr satellite , carbon 13 nmr , proton nmr , spectral line , nuclear magnetic resonance spectroscopy , stereochemistry , crystallography , computational chemistry , fluorine 19 nmr , physics , particle physics , astronomy
The 17 O NMR spectra of six different arylmethylenemalonaldehydes were measured for various solvents and temperatures. The 17 O NMR chemical shifts and line widths of the carbonyl oxygens of the malonaldehyde fragment show a clear variation in the series of monoaryl compounds studied. The differences between the 17 O NMR chemical shifts of the formyl oxygens correlate well with two conformationally dependent 1 H– 1 H and 1 H– 13 C coupling constants for the same compounds. Molecular mechanical calculations were also performed in order to relate the present data with the conformational preferences of the malonaldehyde fragment of the arylmethylenemalonaldehydes.