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• W2024582669 abstract "Substituent mesomeric effects transmitted through cyclopropane have been examined by the influence that a p-x-aryl group (X= OMe, Me, H, Cl) on C2 might have on preferential conformer populations of an aldehyde unit on C1 in solution. The lanthanide induced shift method, which proved to be applicable to this non rigid system by testing the structural self consistency of the model with Ohkata's correlations, was used to determine the preferred CCO rotational angle τ relative to the cyclopropane plane. This gave τ around 30°–50° away from the bisected conformation in the direction of the C1C3 bond, irrespective of the electron withdrawer or donor nature of the arene substituents. This showed that true mesomeric effects do not occur in cyclopropane. Instead, competitive conjugation of substituents for the electron density in the ring is the dominant feature, as predicted by conventional MO theory. Conformational preferences of cyclopropyl aldehydes observed with LIS studies are interpreted as indicators of carbonyl-cyclo-propane conjugation as a function of individual CC bond electron density in the ring, and not as substituent mesomeric effects." @default.
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• W2024582669 date "1993-08-01" @default.
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• W2024582669 title "Transmission of electronic effects through 2-[donor]-1-[acceptor] cyclopropanes. Part III. Conformational studies of 2-(p-x-aryl)-1-cyclopropane aldehydes with lanthanide shift reagents." @default.
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• W2024582669 doi "https://doi.org/10.1016/s0040-4020(01)87219-7" @default.
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