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

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 pul...

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Published in:Physical chemistry chemical physics : PCCP 2017-06, Vol.19 (22), p.14729-14737
Main Authors: Lee, Sung-Sik, Park, Soojin, Hong, Yin, Lee, Jae-Ung, Kim, Jun-Hyeok, Yoon, Dongkyung, Kong, Xianglei, Lee, Sungyul, Oh, Han Bin
Format: Article
Language:English
Subjects:
Alanine
Band spectra
Density functional theory
Differentiation
Lasers
Mathematical analysis
Spectra
Wavelengths
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Summary: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 . 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 ) bands in the observed spectra to the stretch motions of completely isolated alanine -OH groups.
ISSN:1463-9076
1463-9084
DOI:10.1039/c7cp01085k