title: Intermolecular association of tetrahydrofuran-2-carboxylic acid in solution: a vibrational circular dichroism study.
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.
authors.affiliation: Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281-S3, B-9000 Ghent, Belgium.
authors.forename: Tom
authors.initials: T
authors.lastname: Kuppens
authors.forename: Wouter
authors.initials: W
authors.lastname: Herrebout
authors.forename: Benjamin
authors.initials: B
authors.lastname: van der Veken
authors.forename: Patrick
authors.initials: P
authors.lastname: Bultinck
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002942:Circular Dichroism / Q000379:methods*; D003198:Computer Simulation; D019281:Dimerization; D005663:Furans / Q000737:chemistry*; D006860:Hydrogen Bonding; D008956:Models, Chemical; D015394:Molecular Structure; D012680:Sensitivity and Specificity; D012996:Solutions / Q000737:chemistry
chemical_list: D002264:Carboxylic Acids; D005663:Furans; D012996:Solutions; C522346:tetrahydrofuran-2-carboxylic acid