Jump to main content
Jump to site search

Issue 29, 2017
Previous Article Next Article

Solvation of a chiral carboxylic acid: effects of hydrogen bonding on the IR and VCD spectra of α-methoxyphenylacetic acid

Author affiliations

Abstract

Strong hydrogen bonding to solvent molecules can significantly alter the IR and VCD spectra of a chiral solute. This can be particularly troublesome for the determination of absolute configurations, as all spatial configurations of solute–solvent clusters need to be considered explicitly in spectra calculations. With this contribution, we aim to derive general guidelines for the explicit solvation of carboxylic acids, and characterize the solute–solvent interactions of the model compound α-methoxyphenylacetic acid (MPAA) in organic solvents of different polarity. We show that, in the typical concentration range employed for VCD studies, MPAA prefers the formation of dimers in chloroform. In the other investigated solvents (acetonitrile, methanol, and dimethyl sulfoxide), hydrogen bonded solute–solvent clusters have to be considered explicitly for the spectral analysis. We discuss the origin of the solvent dependence of the VCD spectra of MPAA in detail, show which vibrational modes are most strongly affected, and that the spectral response correlates with the hydrogen bonding strength.

Graphical abstract: Solvation of a chiral carboxylic acid: effects of hydrogen bonding on the IR and VCD spectra of α-methoxyphenylacetic acid

Back to tab navigation

Supplementary files

Article information


Submitted
30 Mar 2017
Accepted
12 Jun 2017
First published
12 Jun 2017

Phys. Chem. Chem. Phys., 2017,19, 18948-18956
Article type
Paper

Solvation of a chiral carboxylic acid: effects of hydrogen bonding on the IR and VCD spectra of α-methoxyphenylacetic acid

K. Bünnemann and C. Merten, Phys. Chem. Chem. Phys., 2017, 19, 18948
DOI: 10.1039/C7CP02049J

Social activity

Search articles by author

Spotlight

Advertisements