The effect of solvent on chemical-shift non-equivalence of diastereotopic geminal nuclei in (pro)1-chiral N,N-disubstituted 5-oxo-4-phenyl-2,5-dihydroisoxazol-2-ium-3-olates

Gury Zvilichovsky*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The 1H and 13C resonance shifts of the geminal nuclei in N,N-diethyl, -dibenzyl, -di-isopropyl, and -tetramethylene derivatives of 5-oxo-4-phenyl-2,5-dihydroisoxazol-2-ium-3-olates have been measured in various solvents and (CD3)2SO-CDCl3 mixtures. It is concluded that the accidental isochrony of the geminal hydrogens of the N,N-diethyl derivative in (CD3)2SO is not due to a change in conformation. The aim of this work is to discover whether the changes of the relevant chemical shifts are due to the change in the reaction field at the dipole of the molecule, which differs according to the change in dielectric constant of the medium. The use of solvents less polar than (CD3)2SO as well as of some of higher polarity results in well separated anisochrony of the two geminal hydrogens. The different directions and magnitudes of the solvent effects on the chemical shifts of each of the nuclei in the compounds studied are attributed to their different angles, relative to the direction of the reaction field.

Original languageEnglish
Pages (from-to)2015-2019
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number12
DOIs
StatePublished - 1988

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