Title
Solvent effects on the monomer/hydrogen-bonded dimer equilibrium in carboxylic acids: (+)-(S)-ketopinic acid as a case study Solvent effects on the monomer/hydrogen-bonded dimer equilibrium in carboxylic acids: (+)-(S)-ketopinic acid as a case study
Author
Publication type
article
Publication
Weinheim ,
Subject
Chemistry
Source (journal)
Chemistry: an Asian journal. - Weinheim
Volume/pages
11(2016) :12 , p. 1798-1803
ISSN
1861-4728
ISI
000379519400009
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
The hydrogen-bond-assisted self-association process of a chiral semirigid carboxylic acid, namely, (+)-(S)-ketopinic acid, has been studied. The multiconformational monomer/dimer equilibrium has been evaluated by means of a concentration-dependent FTIR study that enabled the experimental equilibrium constants of the dimer formation reaction (K-dim) to be determined in two solvents of different polarity. In CDCl3, dimeric forms predominate, even in diluted solutions (K-dim(CF) =5.074), whereas in CD3CN the self-association process is hindered and monomers are always the main species, irrespective of solute concentration (K-dim(AN) = 0.194). The reliability of the dimerization constants and the derived mono- and dimeric experimental fractions have been proven by means of accurate matching between the experimental vibrational circular dichroism spectra of the species and the theoretical spectra generated by considering the simultaneous weighted contributions of the concomitant monomers and dimers.
E-info
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https://repository.uantwerpen.be/docman/iruaauth/1bccce/134973.pdf
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