How many solvent molecules are required to solvate chiral 1,2-diols with hydrogen bonding solvents? A VCD spectroscopic study

Abstract

A VCD spectroscopic analysis of selected model systems for solute–solvent interactions of chiral diols with hydrogen bonding solvents DMSO and ACN.

Competition between inter and intramolecular hydrogen bond evidenced by vibrational circular dichroism spectroscopy: The case of (1S,2R)‐(−)‐cis‐1‐amino‐2‐indanol

“…The effect of entropy can also be assessed by comparing the spectra of Figures 5 and 7, obtained from the weighted average of all the conformational variants obtained for each family, with those considering only the most stable geometry of each family (Figures S4 and S5). The latter approach was used successfully by Perera et al and Weirich et al, with the weights of the different clusters obtained by adjustment to the experimental VCD spectrum 63,64 …”

“…The latter approach was used successfully by the groups of Xu and Merten, with the weights of the different clusters obtained by adjustment to the experimental VCD spectrum. 63,64…”

Tackling Stereochemistry in Drug Molecules with Vibrational Optical Activity

“…The inclusion of dimers or explicit solvation can be challenging for non-experts. Recent work by the Merten group, however, has shown that for specific functional groups systematic approaches can be used in a straightforward manner to account for this [ 40 , 41 , 42 , 43 ].…”

Solvation of the Boc–Val–Phe–nPr peptide characterized by VCD spectroscopy and DFT calculations

“…Envisioning a general pragmatic way to predict how and when solute-solvent interactions will affect VCD spectral signatures, we have carried out systematic solvation studies on chiral carboxylic acids, 21,22 alcohols 23,24 and diols. 25 Small peptides [26][27][28][29][30][31][32] have served as model compounds to investigate the combined effect of solvation on spectral signatures and conformational distributions. For instance, we have recently investigated the IR and VCD spectra of Boc-Pro-Phe-nPr (1, Scheme 1), a dipeptide that also served as model compound for b-turn forming peptides.…”