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A VCD robust mode analysis of induced chirality: The case of pulegone in chloroform
Author(s) -
Nicu Valentin Paul,
Debie Elke,
Herrebout Wouter,
Van der Veken Benjamin,
Bultinck Patrick,
Baerends Evert Jan
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20817
Subject(s) - chemistry , chirality (physics) , vibrational circular dichroism , circular dichroism , intermolecular force , molecule , pulegone , computational chemistry , chemical physics , stereochemistry , organic chemistry , physics , quantum mechanics , chiral symmetry breaking , chromatography , essential oil , nambu–jona lasinio model , quark
Vibrational modes in an achiral molecule may acquire rotational strength by complexation to a chiral molecule, as happens for achiral solvent molecules complexed to a chiral solute. We investigate this transfer of chirality in vibrational circular dichroism for the pulegone molecule in CDCl 3 solvent from the point of view of the robustness concept introduced recently. It turns out that the transfer of chirality yields nonrobust modes, which means that, although they are observed in vibrational circular dichroism (VCD) experiments, the sign of these modes cannot be predicted reliably with standard (Density Functional Theory) VCD calculations. This limits the usefulness of the induced chirality phenomenon for obtaining information on the intermolecular interactions that give rise to it. Chirality 21:E287–E297, 2009. © 2010 Wiley‐Liss, Inc.