Premium
Molecular modeling and NMR spectroscopic examination of ( E )‐cyclodec‐5‐enone and its 2 ‐and 10‐methyl analogs
Author(s) -
Chu Yongliang,
Colclough David,
White James B.,
Smith William B.
Publication year - 1993
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.1260311012
Subject(s) - homonuclear molecule , chemistry , heteronuclear molecule , molecular orbital , spectral line , proton nmr , enone , nmr spectra database , proton , two dimensional nuclear magnetic resonance spectroscopy , carbon 13 nmr , computational chemistry , nuclear magnetic resonance , nuclear magnetic resonance spectroscopy , stereochemistry , molecule , organic chemistry , physics , quantum mechanics , astronomy
The 1 H and 13 C NMR spectra of ( E )‐cyclodec‐5‐enone and its 2‐ and 10‐methyl analogs were determined. The 1 H NMR spectrum of the former was determined over the temperature range −60 to 20°C. Information from the 2‐D INADEQUATE spectrum of the parent compound was combined with that derived from the homonuclear and heteronuclear correlation spectra to assign the olefinic proton at C‐6. In all three proton spectra, this was the only set of resonances sufficiently well defined to allow conformational information to be deduced. Molecular modeling by molecular mechanics, semi‐empirical and ab initio molecular orbital methods were used to predict conformational preferences. These results were then compared with the NMR data.