TY - JOUR
T1 - 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
AU - Zvilichovsky, Gury
PY - 1988
Y1 - 1988
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=37049066729&partnerID=8YFLogxK
U2 - 10.1039/P29880002015
DO - 10.1039/P29880002015
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AN - SCOPUS:37049066729
SN - 1472-779X
SP - 2015
EP - 2019
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
IS - 12
ER -