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Paper | Regular issue | Vol 60, No. 1, 2003, pp.89-98
Published online, 15th November, 2002
DOI: 10.3987/COM-02-9623
1H NMR Spectroscopy and Conformational Analysis of N-Benzylimidazolidines

Isabel A. Perillo,* Carlos de los Santos, and Alejandra Salerno

*Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956 (1113) Buenos Aires, Argentina

Abstract

1H NMR spectra of a series of 1-benzyl- and 1,3-dibenzylimidazolidines are analyzed and correlated with their conformational features. The spectra are assigned on the basis of chemical shifts and proton coupling constant values, and confirmed by NOESY spectra. C2-Unsubstituted imidazolidines (1, 9) show a fast inversion of the nitrogen atoms. By contrast, 1,2,3-trisubstituted imidazolidines display a preferential conformation with a transoid orientation of the N1, N3, and C2 substituents.