Intermolecular association of tetrahydrofuran-2-carboxylic acid in solution: a vibrational circular dichroism study |
| |
Authors: | Kuppens Tom Herrebout Wouter van der Veken Benjamin Bultinck Patrick |
| |
Institution: | Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281-S3, B-9000 Ghent, Belgium. |
| |
Abstract: | Carboxylic acids are known for their strong intermolecular associations. With chiral carboxylic acids, this behavior can be studied using vibrational circular dichroism (VCD). Tetrahydrofuran-2-carboxylic acid 1, a chiral building block for beta-lactam antibiotics, is studied by emphasizing the effect of the dimerization. Experimental results indicate that for solutions of 1 in CDCl3 and CS2, a complex equilibrium exists between the monomers and dimers. B3LYP/aug-cc-pVTZ calculations are performed on both monomer and dimer structures. To simulate IR and VCD spectra, populations for monomer and dimers were approximated using a semiquantitative model. A good agreement between experimental and simulated spectra is obtained by taking into account both the monomeric and the dimeric structures, weighted using the experimentally determined populations. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|