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Conformational Flexibility of Limonene Oxide Studied By Microwave Spectroscopy
Author(s) -
Loru Donatella,
QuesadaMoreno María Mar,
AvilésMoreno Juan Ramón,
Jarman Natasha,
Huet Thérèse R.,
LópezGonzález Juan Jesús,
Sanz M. Eugenia
Publication year - 2017
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201600991
Subject(s) - conformational isomerism , rotational spectroscopy , chemistry , steric effects , spectroscopy , ab initio , ab initio quantum chemistry methods , limonene , photochemistry , hydrogen bond , potential energy surface , computational chemistry , stereochemistry , organic chemistry , molecule , physics , chromatography , quantum mechanics , essential oil
Abstract Monoterpenoids are biogenic volatile organic compounds that play a major role in atmospheric chemistry by participating in the formation of aerosols. In this work, the monoterpenoid ( R )‐(+)‐limonene oxide (C 10 H 16 O) was characterized in the gas phase by Fourier‐transform microwave spectroscopy in a supersonic jet. Five conformers of limonene oxide, four equatorial and one axial considering the configuration of the isopropenyl group, were unambiguously identified from analysis of the rotational spectrum. The observed conformers include cis and trans forms, which are stabilized by a subtle balance of hydrogen bonds, dispersive interactions, and steric effects. Estimated conformational relative abundances surprisingly reveal that the abundance of the axial conformer is similar to that of some of the equatorial conformers. In addition, the potential energy surface was extensively explored by using density functional theory and ab initio methods.