Torsional chirality and molecular recognition: the homo and heterochiral dimers of thenyl and furfuryl alcohol

Abstract

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...

The evolution towards cyclic structures in the aggregation of aromatic alcohols: the dimer, trimer and tetramer of 2-phenylethanol

“…18,23,24 Furthermore, interesting modulations in non-covalent interactions can be achieved by combination of additional chemical groups, like heteroatoms or aliphatic rings, paving the way for the rational design of macromolecular entities. 25,26 For aliphatic compounds, we developed a new laser technique that combines ns and fs laser sources to record mass-resolved IR spectra of molecules without chromophore. 27,28…”

“…18,23,24 Furthermore, interesting modulations in non-covalent interactions can be achieved by combination of additional chemical groups, like heteroatoms or aliphatic rings, paving the way for the rational design of macromolecular entities. 25,26 For aliphatic compounds, we developed a new laser technique that combines ns and fs laser sources to record mass-resolved IR spectra of molecules without chromophore. 27,28 The self-aggregation of the simple aromatic alcohols phenol (PhOH), 29,30 benzyl alcohol (BzOH) 31 and furfuryl alcohol, 25 has recently been compared with the thiol and amine derivatives thiophenol, 26 benzyl mercaptan 32 and aniline.…”

“…25,26 For aliphatic compounds, we developed a new laser technique that combines ns and fs laser sources to record mass-resolved IR spectra of molecules without chromophore. 27,28 The self-aggregation of the simple aromatic alcohols phenol (PhOH), 29,30 benzyl alcohol (BzOH) 31 and furfuryl alcohol, 25 has recently been compared with the thiol and amine derivatives thiophenol, 26 benzyl mercaptan 32 and aniline. 33 The aromatic alcohols present interesting connections between intramolecular interactions and conformational properties, which become more complex with each additional methylene group.…”

Sulfur–arene interactions: the S⋯π and S–H⋯π interactions in the dimers of benzofuran⋯sulfur dioxide and benzofuran⋯hydrogen sulfide

“…This energetic distribution is probably associated to the prevailing role in these complexes of the π ring electronic density and the large and polarizable molecular orbital distribution in the sulfur triatomics. In this sense both the S⋯π and S–H⋯π interactions occupy an intermediate position between the dominant dispersive character observed in π-stacking 26,27,55 and dimers involving a primary hydrogen bond, particularly alcohols, 56–58 but also some thiols like the prototypic hydrogen sulfide dimer. 59 On the other hand, the dimer of benzyl mercaptan, 60 which combines S–H⋯S and S–H⋯π interactions, presents an energy distribution close to the benzofuran dimers.…”

Assignment of the absolute configuration of molecules that are chiral by virtue of deuterium substitution using chiral tag molecular rotational resonance spectroscopy

“…This work supports the emerging consensus from the rotational spectroscopy community that CREST is a highly successful method for identifying the low-energy isomers of weakly bound complexes. 50,51,[77][78][79][80][81][82][83][84][85][86][87][88][89][90][91][92][93] Further, geometry optimization using dispersion corrected DFT gives chiral tag complex equilibrium geometries with sufficient accuracy to make a high-confidence determination of the analyte absolute configuration.…”