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Chirality‐Induced Switch in Hydrogen‐Bond Topology: Tetrameric Methyl Lactate Clusters in the Gas Phase
Author(s) -
Adler Thomas B.,
Borho Nicole,
Reiher Markus,
Suhm Martin A.
Publication year - 2006
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.200600380
Subject(s) - enantiopure drug , chemistry , chirality (physics) , hydrogen bond , gas phase , crystallography , cluster (spacecraft) , stoichiometry , hydrogen , topology (electrical circuits) , stereochemistry , computational chemistry , molecule , enantioselective synthesis , organic chemistry , catalysis , chiral symmetry breaking , symmetry breaking , physics , mathematics , quantum mechanics , combinatorics , nambu–jona lasinio model , computer science , programming language
Supersonic jet expansions of racemic methyl lactate show a prominent OH‐stretching infrared absorption at 3401 cm −1 which is not present in the enantiopure compound. Experimental results and quantum chemical calculations show that the underlying tetrameric cluster has 2:2 stoichiometry of the R and S isomers and S 4 symmetry (see picture; C orange, O red, H gray).