Unusual H‐Bond Topology and Bifurcated H‐bonds in the 2‐Fluoroethanol Trimer |
| |
Authors: | Dr. Javix Thomas Dr. Xunchen Liu Prof. Dr. Wolfgang Jäger Prof. Dr. Yunjie Xu |
| |
Affiliation: | 1. Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada);2. School of Mechanical Engineering, Shanghai Jiao Tong University, No.800 Dong Chuan Road, Shanghai, 200240 (P.R. China) |
| |
Abstract: | By using a combination of rotational spectroscopy and ab initio calculations, an unusual H‐bond topology was revealed for the 2‐fluoroethanol trimer. The trimer exhibits a strong heterochiral preference and adopts an open OH???OH H‐bond topology while utilizing two types of bifurcated H‐bonds involving organic fluorine. This is in stark contrast to the cyclic OH???OH H‐bond topology adopted by trimers of water and other simple alcohols. The strengths of different H‐bonds in the trimer were analyzed by using the quantum theory of atoms in molecules. The study showcases a remarkable example of a chirality‐induced switch in H‐bond topology in a simple transient chiral fluoroalcohol. It provides important insight into the H‐bond topologies of small fluoroalcohol aggregates, which are proposed to play a key role in protein folding and in enantioselective reactions and separations where fluoroalcohols serve as a (co)solvent. |
| |
Keywords: | bifurcated H‐bonds chirality fluoroalcohols H‐bond topology rotational spectroscopy |
|
|