title: Monosolvation of R-1-phenyl-2,2,2-trifluoroethanol with amines: configurational effects on the excitation, ionization, and fragmentation of diastereomeric complexes.
abstract: Wavelength and mass selected resonant two-photon ionization spectra of molecular clusters between R-1-phenyl-2,2,2-trifluoroethanol (FER) and methylamine (M) or the enantiomers of 2-aminobutane (AR and AS) were recorded after supersonic molecular beam expansion and analyzed with the aid of ab initio molecular orbital calculations. The experimental results agree with theoretical calculations pointing to the predominance of the two most stable conformers of monosolvated FER whose CF3 group establishes intense NH...F interactions with the selected amines so as to orient them away from the aromatic ring. This reduces the enantioselectivity of FER toward the 2-aminobutane enantiomers as compared to that exhibited by the R-1-phenylethanol (ER) analogue, where obviously NH...F interactions are absent.
authors.affiliation: Dipartimento di Chimica, Università di Roma La Sapienza, P. zle Aldo Moro 5, I-00185 Rome, Italy. anna.giardini@uniroma1.it
authors.forename: Anna
authors.initials: A
authors.lastname: Giardini
authors.forename: Gianfranco
authors.initials: G
authors.lastname: Cattenacci
authors.forename: Alessandra
authors.initials: A
authors.lastname: Paladini
authors.forename: Susanna
authors.initials: S
authors.lastname: Piccirillo
authors.forename: Mauro
authors.initials: M
authors.lastname: Satta
authors.forename: Flaminia
authors.initials: F
authors.lastname: Rondino
authors.forename: Maurizio
authors.initials: M
authors.lastname: Speranza
mesh_terms: D000588:Amines / Q000737:chemistry*; D007477:Ions; D008968:Molecular Conformation; D012995:Solubility; D013237:Stereoisomerism; D014270:Trifluoroethanol / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: C528617:1-phenyl-2,2,2-trifluoroethanol; D000588:Amines; D007477:Ions; D014270:Trifluoroethanol