Chiral differentiation of d- and l-alanine by permethylated β-cyclodextrin: IRMPD spectroscopy and DFT methods

Literature Information

Publication Date 2017-05-10
DOI 10.1039/C7CP01085K
Impact Factor 3.676
Authors

Sung-Sik Lee, Soojin Park, Jae-ung Lee, Jun-Hyeok Kim, Dongkyung Yoon, Sungyul Lee, Han Bin Oh


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Abstract

The gaseous chiral differentiation of alanine by permethylated β-cyclodextrin was studied using IRMPD spectroscopy and density functional theory calculations. The protonated non-covalent complexes of permethylated β-cyclodextrin and D- or L-alanine were mass-selected and investigated by IR laser pulses in the wavelength region of 2650–3800 cm−1. The remarkably different features of the IRMPD spectra for D- and L-alanine are described, and their origin is elucidated by quantum chemical calculations. We show that the differentiation of the experimentally observed spectral features is the result of different local interactions of D- and L-alanine with permethylated β-cyclodextrin. We also assign the extremely high-frequency (>3700 cm−1) bands in the observed spectra to the stretch motions of completely isolated alanine –OH groups.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
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