The conformational landscape of perillyl alcohol revealed by broadband rotational spectroscopy and theoretical modeling

Xie, Fan

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https://hdl.handle.net/2142/104258 Copy

Description

Title

The conformational landscape of perillyl alcohol revealed by broadband rotational spectroscopy and theoretical modeling

Author(s)

Xie, Fan

Contributor(s)

• Xu, Yunjie
• Jäger, Wolfgang
• Thomas, Javix
• Heger, Matthias
• Seifert, Nathan A.

Issue Date

2019-06-17

Keyword(s)

Non-covalent interactions

Abstract

Perillyl alcohol (PA) is a naturally occurring dietary monoterpene that can be extracted from various plants, such as lavender and peppermint, and its application to human cancer treatment has been explored.$^{1}$ The rotational spectrum of PA has been investigated using a chirped-pulse Fourier transform microwave (FTMW) spectrometer and a cavity FTMW spectrometer. In parallel, we have carried out extensive conformational searches by scanning relevant dihedral angles and also using a semi-classical conformational search program, GFN-xTB.$^{2}$ In total, 108 conformers have been identified and confirmed to be true minima with the subsequent DFT calculations. The relative stabilities of the conformers identified and the interconversion barriers among them have been explored at the MP2/6-311++G(2d,p) and B3LYP-D3(BJ)/def2-TZVP levels of theory. Experimentally, 8 conformers have been assigned and the missing low energy conformers have been rationalized in terms of conformational conversion barriers under a jet expansion condition. A comprehensive study on the conformational distribution of PA may facilitate our understanding of its structural property and possible structural-functional relationship. 1 T. C. Chen, C. O Da Fonseca, A. H Schönthal. Am. J. Cancer Res. 2015, 5, 1580. 2. S. Grimme, C. Bannwarth, P. Shushkov, J. Chem. Theo. Comput. 2017, 13, 1989.

Publisher

International Symposium on Molecular Spectroscopy

Type of Resource

text

Language

eng

Permalink

http://hdl.handle.net/2142/104258

DOI

https://doi.org/10.15278/isms.2019.MH09

Copyright and License Information

Copyright 2019 Fan Xie

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