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A conformational investigation of zearalenone and the 6′‐zearalenols by carbon and proton NMR spectroscopy
Author(s) -
Smith William B.,
Watson William H.
Publication year - 1987
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.1260251110
Subject(s) - chemistry , conformational isomerism , molecule , relaxation (psychology) , nuclear magnetic resonance spectroscopy , proton , spectroscopy , proton nmr , zearalenone , nmr spectra database , computational chemistry , crystallography , spectral line , stereochemistry , organic chemistry , psychology , social psychology , physics , food science , quantum mechanics , astronomy , aflatoxin
The carbon and proton spectra for zearalenone and its two C‐6′ alcohol derivatives have been assigned using 2D techniques along with NOE difference spectra and the LIS of the dimethoxy derivative of the β‐alcohol. Low temperature and relaxation time studies on the latter compound support the existence of only one solution conformer for each molecule. Molecular mechanics calculations for each molecule predict the existence of several low energy conformers which differ in energy by less than 3 kcal/mol; however, barriers to conformational interchange could not be estimated. Partial analysis of the proton spectra allows a comparison of the NMR parameters with the MM derived conformations and with x‐ray structural data. The solution conformations of zearalenone and α‐zearalenol are closely related to the solid state conformations.