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

Literature Information

Publication Date 2019-07-02
DOI 10.1039/C9CP03028J
Impact Factor 3.676
Authors

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


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Abstract

The rotational spectrum of perillyl alcohol, a naturally occurring, chiral, dietary monoterpene, was investigated using a chirped pulse Fourier transform microwave spectrometer and a cavity-based Fourier transform microwave spectrometer. To aid the assignment of the dense chirped pulse spectrum obtained, extensive theoretical conformational searches were carried out. In one approach, several one and two-dimensional scans along three dihedral angles associated with the rotational motions of the –OH, –CH2OH, and –C(CH2)CH3 groups were performed. These scans, combined with the equatorial and axial positions of the –C(CH2)CH3 group, resulted in 54 conformers. The same conformers were identified in the second approach where a semi-classical conformational search code was used. The relative stabilities of the conformers and the interconversion barriers among them were explored extensively at the DFT B3LYP-D3(BJ)/def2-TZVP and B3LYP-D3(BJ)/6-311++G(2d,p), as well as local MP2/aug-cc-pVQZ levels of theory, and 12 conformers were ultimately identified as possibly observable candidates in a molecular jet expansion. Rotational spectra of eight out of the 12 candidates were observed experimentally and analyzed. The non-observation of the remaining four conformers may be attributed to their low abundances. The study points out the importance of identifying all conformers of relevant abundance, even those which could not be detected experimentally, in order to properly benchmark the theoretical relative stabilities with the experimental ones. A comprehensive study of the conformational distribution of perillyl alcohol contributes to our understanding of its structural properties which may influence its functions.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
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Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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