Lactic acid in solution: investigations of lactic acid self-aggregation and hydrogen bonding interactions with water and methanol using vibrational absorption and vibrational circular dichroism spectroscopies

The Journal of Chemical Physics
Martin LosadaYunjie Xu

Abstract

The infrared vibrational absorption (VA) and vibrational circular dichroism (VCD) spectral features of L-(+)-lactic acid (LA) in CDCl3 solution are concentration dependent, showing evidence of oligomerization with increasing concentrations. To understand the observed spectra, geometry optimizations, vibrational frequencies, and VA and VCD intensities were evaluated for (LA)n with n=1-4 using density functional theory calculations at the B3LYP6-311++G(d,p), B3LYP/cc-pVTZ, and in some cases, B3LYP/aug-cc-pVTZ levels of theory. Comparisons with the experimental spectra indicate that the lowest energy LA dimer (AA), formed by two C Double Bond O...HO hydrogen bonds, is one of the dominating species in solution at room temperature. Possible contributions from the LA trimer and tetramer are also discussed. To model the VA and VCD spectra of LA in water and in methanol, both implicit polarizable continuum model and explicit hydrogen bonding considerations were used. For explicit hydrogen bonding, geometry optimizations of the AA-(water)n and AA-(methanol)n complexes, with n=2,4,6, were performed, and the corresponding VA and VCD spectra were simulated. Comparisons of the calculated and experimental VA and VCD spectra in the range of 1...Continue Reading

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Citations

Jan 6, 2010·Chirality·Valentin Paul NicuEvert Jan Baerends
Oct 6, 2016·Journal of Chemical Theory and Computation·Tommaso GiovanniniChiara Cappelli
Jun 1, 2017·Physical Chemistry Chemical Physics : PCCP·Christian Merten
Jun 27, 2017·Physical Chemistry Chemical Physics : PCCP·Karoline Bünnemann, Christian Merten
Dec 23, 2015·Physical Chemistry Chemical Physics : PCCP·Adéla MelcrováJakub Kaminský
May 17, 2018·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Angelo Shehan PereraYunjie Xu
Jun 13, 2008·Physical Chemistry Chemical Physics : PCCP·Elke DebieBenjamin van der Veken
Nov 19, 2008·Physical Chemistry Chemical Physics : PCCP·Guochun Yang, Yunjie Xu
Jun 24, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Guochun YangYufen Zhao
Apr 27, 2010·Chemical Society Reviews·Joanna SadlejJoanna E Rode
Jun 28, 2011·Physical Chemistry Chemical Physics : PCCP·Sándor GóbiGyörgy Tarczay
Feb 16, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Peiyang ZhuYunjie Xu
Mar 22, 2018·Physical Chemistry Chemical Physics : PCCP·Tommaso GiovanniniChiara Cappelli
May 1, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Mohammad Reza PoopariYunjie Xu
Sep 4, 2014·Physical Chemistry Chemical Physics : PCCP·Sanehiro MuromachiSatoshi Takeya
Dec 19, 2012·Physical Chemistry Chemical Physics : PCCP·Mohammad Reza PoopariYunjie Xu
May 26, 2018·Chemistry : a European Journal·Dennis GerbigPeter R Schreiner
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Apr 6, 2011·Physical Chemistry Chemical Physics : PCCP·Valentin Paul NicuEvert Jan Baerends
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Jul 9, 2008·The Journal of Physical Chemistry. B·Young Kee Kang, Byung Jin Byun
May 5, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Yanqing YangYunjie Xu

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Methods Mentioned

BETA
nuclear magnetic resonance
NMR
x-ray crystallography
circular dichroism
PMA

Software Mentioned

GAUSSIAN03
GAUSSVIEW

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