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 S4 symmetry (see picture; C orange, O red, H gray).
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Adler et al. (2006) studied this question.
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