Ultraviolet and infrared spectroscopy of neutral and ionic non-covalent diastereomeric complexes in the gas phase

Rendiconti Lincei - Tập 24 - Trang 259-267 - 2013
Flaminia Rondino1, Alessandra Ciavardini2,3, Mauro Satta4, Alessandra Paladini5, Caterina Fraschetti3, Antonello Filippi3, Bruno Botta3, Andrea Calcaterra3, Maurizio Speranza3, Anna Giardini5, Susanna Piccirillo2
1C.R. ENEA Frascati, Rome, Italy
2Dip. di Scienze e Tecnologie Chimiche, Università di Roma “Tor Vergata”, Rome, Italy
3Dip.di Chimica e Tecnologie del Farmaco, Università di Roma “La Sapienza”, Rome, Italy
4CNR-ISMN, Rome, Italy
5CNR-IMIP, Tito Scalo, Italy

Tóm tắt

Non-covalent intermolecular interactions responsible for chiral discrimination have been investigated in the gas phase both in neutral and ionic complexes. Mass-selected resonant two-photon ionization (R2PI) as well as infrared depleted R2PI (IR–R2PI) techniques have been applied to investigate the role of fluorine substitution in the chiral recognition process between (R)-1-phenyl 1-ethanol (ER), (S)-1-(4-fluorophenyl)-ethanol (pFES), (R)-1-phenyl-2,2,2-trifluoroethanol (FER) and the two enantiomers of butan-2-ol (BR/S), generated in a supersonic molecular beam. The results have been interpreted with the aid of theoretical predictions at the D-B3LYP/6-31G** level of theory. The diastereomeric complexes of ER and pFES with R- and S-butan-2-ol are structurally similar, and dispersive interactions between the aliphatic chain of the alcohol and the π system of the chromophore as well repulsive interactions are mainly responsible for chiral recognition. FER forms, predominantly with S-butan-2-ol, also stable complexes in which the alcohol is oriented away from the aromatic ring. The ionic complexes between pure enantiomers of the bis (diamido)-bridged basket resorcin[4]arene and cytarabine are generated in the gas phase by electrospray ionization and investigated by IRMPD. The proton-bound diastereomers show clearly different IRMPD spectra which, in light of ONIOM (B3LYP/6-31(d):UFF) calculations, are consistent with the occurrence of several isomeric structures, in which the N(3)-protonated guest is either accommodated inside the host cavity or outside it. The spectral differences are attributed to the effects of the intramolecular hydrogen bonding between the C(2′)_OH group and the aglycone oxygen atom of the nucleosidic guest upon repulsive interactions between the same oxygen atom and the aromatic rings of the host.

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Rendiconti Lincei

Tập 24

259-267

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