Chirality‐Induced Switch in Hydrogen‐Bond Topology: Tetrameric Methyl Lactate Clusters in the Gas Phase | Zendy

Adler Thomas B. | Zendy; Borho Nicole | Zendy; Reiher Markus | Zendy; Suhm Martin A. | Zendy

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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).

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