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• W2085799095 abstract "The NMR spectra of a number of 2,4-disubstituted 1,3-dioxolanes have been recorded and the proton chemical shifts and coupling constants derived from complete spectral analysis. Vicinal coupling constants were found to be dependent on the substituent at C-4 and this effect is more pronounced for J(trans) of the C-4-C-5 fragment. These coupling constants also indicate a homogeneous behaviour within a series with either a cis or trans configuration, although the cis behaviour differs from that of trans isomers. This has been interpreted in terms of definite ring conformations in substituted derivatives, while the unsubstituted 1,3-dioxolane undergoes free pesudorotation. Calculations of coupling constants were performed by semi-empirical MO methods, both for unsubstituted 1,3-dioxolane and for C-4 substituted derivatives in a large number of conformations, in order to compare calculated and experimental values; the correct order of J(cis) and J(trans) for 1,3-dioxolane is obtained only by employing energies from ab-initio MO calculations averaged over the pseudorotation circuit. For the C-4 substituted compounds calculated coupling constants were employed in a ‘trial and error’ process for the identification of the preferred conformations of these compounds; a set of two torsional angles for each compound was derived which allows a tentative description of the geometry of each molecule. A criticism of these geometries is given according to the evidence available on the structure of substituted 1,3-dioxolanes." @default.
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• W2085799095 date "1980-01-01" @default.
• W2085799095 modified "2023-09-27" @default.
• W2085799095 title "NMR spectra, MO calculations of spin-spin coupling constants and conformational analysis of substituted 1,3-dioxolanes" @default.
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• W2085799095 doi "https://doi.org/10.1002/mrc.1270130105" @default.
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