Vicinal C,H spin coupling in substituted alkenes. Stereochemical significance and structural effects
Тип публикации: Journal Article
Дата публикации: 1975-12-01
SCImago Q3
WOS Q3
БС2
SJR: 0.365
CiteScore: 3.5
Impact factor: 2.1
ISSN: 07491581, 1097458X
General Chemistry
General Materials Science
Краткое описание
Vicinal C,H spin coupling (3JC,H) in substituted alkenes has been investigated systematically. Emphasis is laid on the stereochemical significance (Jtrans/Jcis) and on the various structural factors which influence 3JC,H, such as π-bond order, torsional angle ϕ, bond angle θ, electronegativity of substituents and steric effects. A new type of γ-effect is observed in 3JtransC,H which appears to have the same origin as the γ-shift effect. By comparison of 3J and 3JH,H, it was found that the relation 3JC,H ≈ 0·6 3JH,H holds for both trans and cis coupling constants. Finally, it is concluded that 3JC,H constitutes a valuable criterion to distinguish E- and Z-isomers, particularly in trisubstituted alkenes. Applications to natural products are presented.
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Vögeli U., Von Philipsborn W. Vicinal C,H spin coupling in substituted alkenes. Stereochemical significance and structural effects // Magnetic Resonance in Chemistry. 1975. Vol. 7. No. 12. pp. 617-627.
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Vögeli U., Von Philipsborn W. Vicinal C,H spin coupling in substituted alkenes. Stereochemical significance and structural effects // Magnetic Resonance in Chemistry. 1975. Vol. 7. No. 12. pp. 617-627.
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TY - JOUR
DO - 10.1002/mrc.1270071213
UR - https://doi.org/10.1002/mrc.1270071213
TI - Vicinal C,H spin coupling in substituted alkenes. Stereochemical significance and structural effects
T2 - Magnetic Resonance in Chemistry
AU - Vögeli, U
AU - Von Philipsborn, W
PY - 1975
DA - 1975/12/01
PB - Wiley
SP - 617-627
IS - 12
VL - 7
SN - 0749-1581
SN - 1097-458X
ER -
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@article{1975_Vögeli,
author = {U Vögeli and W Von Philipsborn},
title = {Vicinal C,H spin coupling in substituted alkenes. Stereochemical significance and structural effects},
journal = {Magnetic Resonance in Chemistry},
year = {1975},
volume = {7},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002/mrc.1270071213},
number = {12},
pages = {617--627},
doi = {10.1002/mrc.1270071213}
}
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MLA
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Vögeli, U., and W Von Philipsborn. “Vicinal C,H spin coupling in substituted alkenes. Stereochemical significance and structural effects.” Magnetic Resonance in Chemistry, vol. 7, no. 12, Dec. 1975, pp. 617-627. https://doi.org/10.1002/mrc.1270071213.
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