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

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  • Ultraviolet and infrared spectroscopy of neutral and ionic non-covalent diastereomeric complexes in the gas phase (Articolo in rivista) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1007/s12210-013-0241-5 (literal)
Alternative label
  • Rondino, F.a, Ciavardini, A.bc, Satta, M.d, Paladini, A.e, Fraschetti, C.c, Filippi, A.c, Botta, B.c, Calcaterra, A.c, Speranza, M.c, Giardini, A.e, Piccirillo, S.b (2013)
    Ultraviolet and infrared spectroscopy of neutral and ionic non-covalent diastereomeric complexes in the gas phase
    in Rendiconti lincei. Scienze fisiche e naturali; Springer Verlag Italia, Milano (Italia)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Rondino, F.a, Ciavardini, A.bc, Satta, M.d, Paladini, A.e, Fraschetti, C.c, Filippi, A.c, Botta, B.c, Calcaterra, A.c, Speranza, M.c, Giardini, A.e, Piccirillo, S.b (literal)
Pagina inizio
  • 259 (literal)
Pagina fine
  • 267 (literal)
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  • http://link.springer.com/article/10.1007%2Fs12210-013-0241-5 (literal)
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  • 24 (literal)
Rivista
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  • 9 (literal)
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  • 3 (literal)
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  • ISI Web of Science (WOS) (literal)
  • Scopu (literal)
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  • a C.R. ENEA Frascati, Via E. Fermi 45, Frascati, 00044 Rome, Italy b Dip. di Scienze e Tecnologie Chimiche, Universit√† di Roma Tor Vergata, via della Ricerca Scientifica, 00133 Rome, Italy c Dip.di Chimica e Tecnologie Del Farmaco, Universit√† di Roma la Sapienza, Rome, Italy d CNR-ISMN, Rome, Italy e CNR-IMIP, Tito Scalo Potenza, Italy (literal)
Titolo
  • Ultraviolet and infrared spectroscopy of neutral and ionic non-covalent diastereomeric complexes in the gas phase (literal)
Abstract
  • 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 (pFE S), (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 ? 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. (literal)
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