Size-selected methyl lactate clusters: fragmentation and spectroscopic fingerprints of chiral recognition

Physical Chemistry Chemical Physics : PCCP
Michal FárníkMartin A Suhm

Abstract

A comprehensive experimental study of the OH stretching vibrations of size-selected clusters of enantiopure and racemic methyl lactate is presented. For the size selection, we measured angular dependent mass spectra and time-of-flight distributions at the different fragment masses. In this way the fragmentation of these clusters upon electron impact ionization is obtained. The largest fragment masses of the neutral (MLac)n clusters are the protonated (MLac)n-1H+ ions. The results of a pressure dependent study in an FTIR jet experiment are compared with completely size-selected experiments based on atomic beam deflection and depletion spectroscopy. The size assignments and spectra agree for dimers and trimers. Structures and spectral information for the trimer and the tetramer at density functional and MP2 level are provided. Selective self-aggregation and chiral recognition was observed for homochiral trimers. They exhibit a ring structure bound by OH...OH hydrogen bonds. A spectacular switch in the hydrogen bonding topology was observed for the tetramer. The homochiral enantiomer exhibits cooperative OH...OH bonding, while the heterochiral version shows isolated OH...O=C bonding in a symmetric SRSR arrangement. The crucial ing...Continue Reading

References

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Dec 20, 2003·Organic & Biomolecular Chemistry·Nicole Borho, Martin A Suhm

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Citations

Aug 22, 2015·The Journal of Physical Chemistry. a·Sidsel D SchrøderHenrik G Kjaergaard
Nov 28, 2017·Mass Spectrometry Reviews·Michal Fárník, Jozef Lengyel
Sep 27, 2006·Physical Chemistry Chemical Physics : PCCP·Nicole BorhoAnne Zehnacker
Aug 11, 2007·Physical Chemistry Chemical Physics : PCCP·Barbara M GiulianoMauro Satta
Jun 5, 2013·Physical Chemistry Chemical Physics : PCCP·M A Suhm, F Kollipost
Aug 13, 2008·Angewandte Chemie·Anne Zehnacker, Martin A Suhm
May 11, 2007·The Journal of Physical Chemistry. a·Santiago Aparicio
Oct 4, 2011·Journal of the American Chemical Society·Archna SharmaTayur N Guru Row
Jan 25, 2018·The Journal of Physical Chemistry. B·Sourav Palchowdhury, B L Bhargava

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