Reverse Perlin effects for all CH bonds in 1,3-Dithiane.
作者： Eusebio Juaristi , Gabriel Cuevas
DOI: 10.1016/S0040-4039(00)74158-X
关键词:
摘要: The reverse Perlin effects observed for all CH 1J coupling constants in 1,3-dithiane, i.e., 1J(CHa x) > 1J(CHe q), seem to support the existence of a dominant σc - s→σ*c h stereoelectronic interaction, which leads weakening equatorial CH bonds this heterocycle.
elsevier.com
sci-hub.se 参考文章(10)
Robert R. Fraser, Monique Bresse, The effect of stereochemistry on 1JC—H at the sp2 carbons of oxime, hydrazone, and imine derivatives of aldehydes Canadian Journal of Chemistry. ,vol. 61, pp. 576- 578 ,(1983) , 10.1139/V83-102
J Kowalewski, Calculations of nuclear spin—spin coupling constants Progress in Nuclear Magnetic Resonance Spectroscopy. ,vol. 11, pp. 1- 78 ,(1977) , 10.1016/0079-6565(77)80013-7
Vanga S. Rao, Orientation of the methoxyl group in cis- and trans-2-methoxy-4-methyl-1,3-dioxanes and related compounds as inferred by 1H and 13C nmr spectroscopy. The significance of the "exo-anomeric" effect Canadian Journal of Chemistry. ,vol. 60, pp. 1067- 1072 ,(1982) , 10.1139/V82-158
Saul Wolfe, B. Mario Pinto, Vikram Varma, Ronald Y. N. Leung, The Perlin Effect: bond lengths, bond strengths, and the origins of stereoelectronic effects upon one-bond C–H coupling constants Canadian Journal of Chemistry. ,vol. 68, pp. 1051- 1062 ,(1990) , 10.1139/V90-164
Saul Wolfe, Chan-Kyung Kim, A theoretical study of conformational deuterium isotope effects and bond dissociation energies of diastereotopic hydrogens Canadian Journal of Chemistry. ,vol. 69, pp. 1408- 1412 ,(1991) , 10.1139/V91-208
Ernest L. Eliel, Robert O. Hutchins, Conformational analysis. XVIII. 1,3-Dithianes. Conformational preferences of alkyl substituents and the chair-boat energy difference Journal of the American Chemical Society. ,vol. 91, pp. 2703- 2715 ,(1969) , 10.1021/JA01038A050
V. A. Chertkov, N. M. Sergeyev, Carbon-13-proton coupling constants in cyclohexane Journal of the American Chemical Society. ,vol. 99, pp. 6750- 6752 ,(1977) , 10.1021/JA00462A045
Marjorie C. Caserio, Phoebe Shih, Cindy L. Fisher, Stereoelectronic effects in ionization reactions of cyclic ortho thioesters Journal of Organic Chemistry. ,vol. 56, pp. 5517- 5521 ,(1991) , 10.1021/JO00019A009
William F. Bailey, Alberto D. Rivera, Kyllikki Rossi, Lone-pair orientation and the magnitude of one-bond CHcoupling adjacent to oxygen and sulfur Tetrahedron Letters. ,vol. 29, pp. 5621- 5624 ,(1988) , 10.1016/S0040-4039(00)80828-X
K. Bock, L. Wiebe, Björn Lindström, Curt R. Enzell, Curt R. Enzell, Carl-Gunnar Swahn, The Effect of Oxygen Lone Paris on 1J(13CH) Values in 1,3-Dioxanes. Acta Chemica Scandinavica. ,vol. 27, pp. 2676- 2678 ,(1973) , 10.3891/ACTA.CHEM.SCAND.27-2676