The effect of fluorine substitution on chiral recognition: interplay of CH···π, OH···π and CH···F interactions in gas-phase complexes of 1-aryl-1-ethanol with butan-2-ol was written by Ciavardini, Alessandra;Rondino, Flaminia;Paladini, Alessandra;Speranza, Maurizio;Fornarini, Simonetta;Satta, Mauro;Piccirillo, Susanna. And the article was included in Physical Chemistry Chemical Physics in 2013.Recommanded Product: 171032-87-4 This article mentions the following:
The mol. diastereomeric complexes between R-1-phenyl-1-ethanol, S-1-(4-fluorophenyl)ethanol and S-1-(2-fluorophenyl)ethanol and R and S-butan-2-ol, isolated under mol. beam conditions in the gas phase, were studied by mass-selective resonant two-photon ionization (R2PI) and IR depleted R2PI (IR-R2PI). The comparison of the three systems allowed the authors to highlight the significance of specific intermol. interactions in the chiral discrimination process. The interpretation of the results is based on theor. predictions mainly at the D-B3LYP/6-31++G** level of theory. The homo and heterochiral complexes are endowed with fine differences in intermol. interactions, strong OH···O, and weaker CH···π, OH···π, CH···F as well as repulsive interactions. The presence of a fluorine atom in the para position of the aromatic ring does not influence the overall geometry of the complex while it affects the electron d. in the π system and the strength of CH···π and OH···π interactions. The role and the importance of CH···F intermol. interactions are evident in the complexes with fluorine substitution in the ortho position. While the ortho hetero complex is structurally analogous to the hetero para and nonfluorinated structures, butan-2-ol in the ortho homo adduct adopts a different conformation to establish a CH···F intermol. interaction. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4Recommanded Product: 171032-87-4).
(S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Recommanded Product: 171032-87-4
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts