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• W2059922207 abstract "The influence of electronegative substituents on the N′-methyl group of nicotine upon the conformation of the pyrrolidine ring has been evaluated by the exact analysis of the high field 1H NMR spectra of nicotine (1),N′-ethylnornicotine (2), N′-(2,2-difluoroethyl)-nornicotine (3) and N′-(2,2,2-trifluoroethyl) nornicotine (4). The vicinal coupling constants for the pyrrolidine ring of 1–4 remain nearly constant, suggesting that as the electronegativity of the N′-methyl substituent increases, only very small changes are seen for the C3′—C4′—C5′—N′ and the C2′—C3′—C4′—C5′ dihedral angles. Substitution on the N′-methyl group appears to have little effect on the orientation of the pyridyl ring with respect to the pyrrolidine ring. Ab initio calculations have been performed on the analogous 2-substituted diethylamines (diethylamine, N-ethyl-2-fluoroethylamine, N-ethyl-2,2-difluoroamine, and N-ehtyl-2,2,2-trifluoroethylamine) which constitute substructure models of 1–4. These calculations confirm the NMR results in that they both indicate little, if any, effects on the rotational barriers and conformational energy profiles as a function of number of fluorine atoms." @default.
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• W2059922207 date "1986-01-01" @default.
• W2059922207 modified "2023-09-26" @default.
• W2059922207 title "Assessment of isolated electronic effects on conformation. NMR analysis of nicotine and related compounds and ab initio studies of model compounds" @default.
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• W2059922207 doi "https://doi.org/10.1016/0022-2860(86)80151-x" @default.
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