RT info:eu-repo/semantics/article
T1 Torsional chirality and molecular recognition: the homo and heterochiral dimers of thenyl and furfuryl alcohol
A1 Juanes San José, Marcos
A1 Saragi, Rizalina Tama
A1 Pérez, Cristóbal
A1 Enríquez Giraudo, María Lourdes
A1 Jaraíz Maldonado, Martín
A1 Lesarri Gómez, Alberto Eugenio
AB Furfuryl alcohol and thenyl alcohol contain a labile torsional chiral center, producing transiently chiral enantiomers interconverting in the nanosecond time-scale. We explored chiral molecular recognition using the weakly-bound intermolecular dimers of both alcohols, freezing stereomutation. Supersonic jet broadband microwave spectroscopy revealed homo and heterochiral diastereoisomers for each alcohol dimer and the structural characteristics of the clusters. All dimers are primarily stabilized by a moderately intense O–H⋯O hydrogen bond, but differ in the secondary interactions, which introduce additional hydrogen bonds either to the ring oxygen in furfuryl alcohol or to the π ring system in thenyl alcohol. Density-functional calculations (B2PLYP-D3(BJ)/def2-TZVP) show no clear preferences for a particular stereochemistry in the dimers, with relative energies of the order 1–2 kJ mol−1. The study suggests opportunities for the investigation of chiral recognition in molecules with torsional barriers in between transient and permanent interconversion regimes.
PB Royal Society of Chemistry
SN 1463-9076
YR 2022
FD 2022
LK https://uvadoc.uva.es/handle/10324/65291
UL https://uvadoc.uva.es/handle/10324/65291
LA eng
NO Phys. Chem. Chem. Phys., 2022,24, 8999-9006
NO Producción Científica
DS UVaDOC
RD 26-may-2024