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Direct Spectroscopic Detection of the Orientation of Free OH Groups in Methyl Lactate–(Water) 1,2 Clusters: Hydration of a Chiral Hydroxy Ester
Author(s) -
Thomas Javix,
Sukhorukov Oleksandr,
Jäger Wolfgang,
Xu Yunjie
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201308466
Subject(s) - chirality (physics) , molecule , chemistry , conformational isomerism , spectroscopy , topology (electrical circuits) , chemical physics , computational chemistry , crystallography , stereochemistry , organic chemistry , chiral symmetry , physics , mathematics , quantum mechanics , combinatorics , nambu–jona lasinio model , quark
Hydration of chiral molecules is a subject of significant current interest in light of recent experimental observations of chirality transfer from chiral solutes to water in solution and the important roles which water plays in biological events. Using a broadband chirped pulse and a cavity based microwave spectrometer, we detected spectroscopic signatures of the mono‐ and dihydrates of methyl lactate, a chiral hydroxy ester. Surprisingly, these small hydration clusters show highly specific binding preferences. Not only do they strongly prefer the insertion H‐bonding topology, but they also favor specific pointing direction(s) for their non‐H‐bonded hydroxy group(s). We observed that the particular dihydrate conformer identified is not the most stable one predicted. This work highlights the superior capability of high‐resolution spectroscopy to identify specific water binding topologies, and provides quantitative data to test state‐of‐the‐art theory.