Comparison of the intermolecular energy surfaces of amino acids: orientation-dependent chiral discrimination

The Journal of Physical Chemistry. B
Krishnan Thirumoorthy, Nilashis Nandi

Abstract

In the present work, we compare the intermolecular energy surfaces of the alanine molecule in its neutral and zwitterionic state using ab initio theory (HF/6-311++G) as a function of mutual orientation. Starting from the optimized structures of the nonbonded homochiral (l-l) and heterochiral (d-l) pairs of molecules, the energy surfaces are studied with rigid geometry by varying the distance and orientation. The potential energy surfaces of the l-l and d-l pairs are found to be dissimilar and reflect the underlying chirality of the homochiral pair and racemic nature of the heterochiral pair. The intermolecular energy surface of the l-l pair is more favorable than the corresponding energy surface of the d-l pair. The study, for the first time, reveals clear homochiral preference without use of parameters, which was unobserved in previous detailed simulations but predicted by theory. The electrostatic interaction further augments the chiral discrimination. The basis set superposition error (BSSE) corrected results show enhanced discrimination. Use of higher-level Møller-Plesset perturbation theory (MP2) and further BSSE correction do not change the conclusions made at the Hartree-Fock (HF) level. The major conclusions based on HF...Continue Reading

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Citations

Jan 11, 2012·Environmental Science & Technology·Wondemagegnehu A GezahegneBroder J Merkel
Feb 27, 2013·Inorganic Chemistry·Gabriele A RollaLothar Helm
Oct 23, 2010·Physical Chemistry Chemical Physics : PCCP·Xianggui YeBamin Khomami
Mar 29, 2011·Physical Chemistry Chemical Physics : PCCP·Jean-François Boily, Kevin M Rosso
Sep 29, 2011·Physical Chemistry Chemical Physics : PCCP·Antonio PrestianniCarlo Adamo
Sep 9, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Michael Bühl, Ingmar Grenthe
Aug 21, 2013·Physical Chemistry Chemical Physics : PCCP·Vladimir PomogaevEdward J Maginn
Oct 25, 2006·The Journal of Chemical Physics·Richard L RowleyTapani A Pakkanen
Jul 10, 2008·The Journal of Physical Chemistry. B·Krishnan Thirumoorthy, Nilashis Nandi
Apr 20, 2007·Accounts of Chemical Research·Nilashis Nandi, Dieter Vollhardt
Aug 4, 2007·The Journal of Physical Chemistry. B·Krishnan Thirumoorthy, Nilashis Nandi

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