X-ray and NMR structural investigations of (±) (u) N-(1-phenylethyl)-1-t-butylsulfinyl-1-propenyl-2-amine, C15H23NOS

Autor: Kozerski, L., Kawęcki, R., Urbańczyk-Lipkowska, Z., Krajewski, J. W., Gluziński, P.
Zdroj: Journal of Chemical Crystallography; February 1991, Vol. 21 Issue: 1 p1-8, 8p
Abstrakt: The structure of the title compound has been investigated in the solid state and in solution by X-ray and NMR-NOE methods, respectively. The crystals are monoclinic:P21/c,a=9.828(1),b=12.326(2),c=13.976(2) Å,ß=107.36(1)°. The structure was solved by direct methods, and refined against 2495 unique reflections by a full-matrix, least-squares procedure givingR=0.046. In the solid state the compound exists as theE isomer with unlike relative configurations on asymmetric atoms. In solution the compound is found as a mixture of a single enamine and two imine forms. The MM calculations suggest that of the two possible geometrical isomers of both diastereoisomersu andl of the enamine, theZ forms should be of lower energy. The total recognition of the homonuclear1H NMR-NOE data interpreted in terms of their distance dependence in the two geometrical forms also favors theZ isomer in both diastereomers.
Databáze: Supplemental Index
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