Conformational distribution of baclofen analogues by 1H and 13C NMR analysis and ab initio HF MO STO-3G or STO-3G* calculations

Claude Vaccher, Pascal Berthelot, Michel Debaert, Gaston Vermeersch, René Guyon, Bernard Pirard, Daniel P. Vercauteren, Magdalena Dory, Guy Evrard, François Durant

Research output: Contribution to journalArticlepeer-review

Abstract

The conformations of 3-(substituted furan-2-yl) and 3-(substituted thien-2-yl)-γ-aminobutyric acid 1-9 in solution (D2O) are estimated from high-resolution (300 MHz) 1H NMR coupling data. Conformations and populations of conformers are calculated by means of a modified Karplus-like relationship for the vicinal coupling constants. The results are compared with X-ray crystallographic investigations (torsion angles) and ab initio HF MO ST-3G or STO-3G* calculations. 1H NMR spectral analysis shows how 1-9 in solution retain the preferred g- conformation around the C3C4 bond, as found in the solid state, while a partial rotation is set up around the C2C3 bond: the conformations about C2C3 are all highly populated in solution. The 13C spin-lattice relaxation times are also discussed. © 1993.

Original languageEnglish
Pages (from-to)199-210
Number of pages12
JournalJournal of molecular structure
Volume301
Issue numberC
DOIs
Publication statusPublished - 10 Dec 1993

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