Title :

The conformational landscape of myrtenol: the structure of the hydroxymethyl group and its robustness upon hydration

Author(s) :

Neeman, Elias [Auteur]
Physique Moléculaire aux Interfaces [PMI]
Osseiran, Noureddin [Auteur]
Physique Moléculaire aux Interfaces [PMI]
Huet, Therese [Auteur]
Physique Moléculaire aux Interfaces [PMI]

Journal title :

The Journal of Chemical Physics

Pages :

124301

Publisher :

American Institute of Physics

Publication date :

2022

ISSN :

0021-9606

HAL domain(s) :

Chimie/Chimie théorique et/ou physique

English abstract : [en]

The conformational landscape of myrtenol (2-pinen-10-ol) and its robustness upon hydration were investigated theoretically and experimentally by employing a synergic combination of quantum chemical calculations and Fourier ...
Show more >The conformational landscape of myrtenol (2-pinen-10-ol) and its robustness upon hydration were investigated theoretically and experimentally by employing a synergic combination of quantum chemical calculations and Fourier transform microwave spectroscopy coupled to a supersonic jet expansion. Relaxed potential energy surfaces have been carried out, and the lowest energy conformers of the monomer were found to be associated with different geometries of the hydroxymethyl group from those previously reported [Sedo et al., J. Mol. Spectrosc. 356, 32 (2019)]. Geometry optimizations and harmonic vibrational frequency calculations allowed characterization of the equilibrium structure of the possible conformers of myrtenol. Among the nine predicted structures, four have been observed, analyzed, and identified. The controversy on the geometry was solved with the deuteration of the hydroxyl group, which led to the determination of substitution (rs) geometry, in agreement with the present theoretical results. Interestingly, the four observed conformers exhibit the same orientation of OH as in the allyl alcohol molecule. Furthermore, hydrogen bonding linking myrtenol to water was studied. One monohydrate has been observed and identified. Non-covalent interactions and natural bond orbital analysis were performed to depict the interactions responsible for the stabilization of the observed structure. We conclude that the structure of the hydroxymethyl group is robust and does not change upon hydration.ACKNOWLEDGMENTSShow less >

Language :

Anglais

Popular science :

Non

ANR Project :

Physiques et Chimie de l'Environnement Atmosphérique

Collections :

• Laboratoire de Physique des Lasers, Atomes et Molécules (PhLAM) - UMR 8523

Source :

Harvested from HAL