Conformational structures and dynamics of cis-n-alkenyl amides
Parallel experimental and computational studies of phenyl cis- and trans-n-alkenyl amides (tuberines) have been carried out to probe the structural and dynamic properties with particular attention to interaction between the conjugated enamides chain and the aromatic ring. The cis isomers are non-pla...
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Published in | Journal of molecular structure Vol. 691; no. 1; pp. 235 - 240 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
Elsevier B.V
29.03.2004
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Subjects | |
Online Access | Get full text |
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Summary: | Parallel experimental and computational studies of phenyl
cis- and
trans-n-alkenyl amides (tuberines) have been carried out to probe the structural and dynamic properties with particular attention to interaction between the conjugated enamides chain and the aromatic ring. The
cis isomers are non-planar with 40–50° due to steric interactions between the enamide chain and aromatic ring,whereas the
trans form is essentially planar. Rotation barriers for the carbonyl group about the C–N bond are predicted to be 18–22
kcal/mol at HF, B3LYP, and MP2 levels using the cc-pVDZ basis set. Despite its significant non-planarity,the
cis conformation of tuberine is not found to be significantly less stable than the
trans conformation. |
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ISSN: | 0022-2860 1872-8014 |
DOI: | 10.1016/j.molstruc.2003.12.032 |