Chiral recognition between 1-(4-fluorophenyl)ethanol and 2-butanol: higher binding energy of homochiral complexes in the gas phase.
Diastereomeric adducts between (S)-1-(4-fluorophenyl)-ethanol and R and S 2-butanol, formed by supersonic expansion, have been investigated by means of a combination of mass selected resonant two-photon ionization-spectroscopy and infrared depletion spectroscopy. Chiral recognition is evidenced by the specific spectroscopic signatures of the S(1)← S(0) electronic transition as well as different frequencies and intensities of the OH stretch vibrational mode in the ground state. D-DFT calculations have been performed to assist in the analysis of the spectra and the determination of the structures. The homochiral and heterochiral complexes show slight structural differences, in particular in the interaction of the alkyl groups of 2-butanol with the aromatic ring. The experimental results show that the homochiral [FE(S)·B(S)] complex is more stable than the heterochiral [FE(S)·B(R)] diastereomer in both the ground and excited states. The binding energy difference has been evaluated to be greater than 0.60 kcal mol(-1).
Dip. di Scienze e Tecnologie Chimiche, Università di Roma Tor Vergata, via della Ricerca Scientifica, 00133 Rome, Italy.
Flaminia
F
Rondino
Alessandra
A
Paladini
Alessandra
A
Ciavardini
Annarita
A
Casavola
Daniele
D
Catone
Mauro
M
Satta
Hans Dieter
HD
Barth
Anna
A
Giardini
Maurizio
M
Speranza
Susanna
S
Piccirillo
D000440:Butanols / Q000737:chemistry*; D005740:Gases / Q000737:chemistry*; D013058:Mass Spectrometry; D008962:Models, Theoretical; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013816:Thermodynamics
C541245:2-para-fluorophenylethanol; D000440:Butanols; D005740:Gases; C043958:2-butanol; D010626:Phenylethyl Alcohol