FT-IR spectroscopic, AM1 and PM3 computational studies of conformation of natural products: cytisine

Elzbieta Górnicka; Ewa D Raczyńska

doi:10.1016/s0039-9140(02)00101-7

FT-IR spectroscopic, AM1 and PM3 computational studies of conformation of natural products: cytisine

Talanta. 2002 Jun 10;57(4):609-16. doi: 10.1016/s0039-9140(02)00101-7.

Authors

Elzbieta Górnicka¹, Ewa D Raczyńska

Affiliation

¹ Interdisciplinary Department of Biotechnology, Agricultural University, 02-528 Warszawa, Poland.

PMID: 18968661
DOI: 10.1016/s0039-9140(02)00101-7

Abstract

Infrared spectra were recorded for cytisine (1) and its model compounds: N-methyl-2-pyridone (2) and piperidine (3) in solution. Eight solvents of different polarity, polarizability and acid-base properties: CCl(4), CS(2), CHCl(3), CDCl(3) (for comparison with the NMR spectra), CH(2)Cl(2), MeOH, Et(2)O and Et(3)N were chosen. Experimental FT-IR spectra were analysed with the help of those calculated for isolated derivatives at the AM1 and PM3 levels. Influence of environment on the conformational preferences in solvated cytisine was discussed and compared with those in the solid state (X-ray measurements) and in the gas phase (quantum-mechanical calculations).