Sniffing out camphor: the fine balance between hydrogen bonding and London dispersion in the chirality recognition with alpha-fenchol
Metadatos
Afficher la notice complèteEditorial
Royal Society of Chemistry
Date
2022-05-03Referencia bibliográfica
Phys. Chem. Chem. Phys., 2022, Advance Article. DOI: [10.1039/d2cp00308b]
Patrocinador
German Research Foundation (DFG) SCHN1280/4-2 271359857 Su 121/5-2 271107160 SPP 1807; Fundacion Alfonso Martin Escudero; Spanish Government FJC2018-035709-IRésumé
Binary complexes between the chiral monoterpenoids camphor and a-fenchol were explored with
vibrational and rotational jet spectroscopy as well as density functional theory in order to explore how
chirality can influence the binding preferences in gas-phase complexes. The global minimum structures
of the two diastereomers were assigned. It is found that chirality recognition leads to different
compromises in the fine balance between intermolecular interactions. While one isomer features a
stronger hydrogen bond, the other one is more tightly arranged and stabilized by larger London
dispersion interactions. These new spectroscopic results help understand the influence of chirality in
molecular aggregation and unveil the kind of interactions involved between a chiral alcohol and a chiral
ketone with large dispersion contributions.