http://www.cnr.it/ontology/cnr/individuo/prodotto/ID250041

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

Type

Prodotto della ricerca (Classe)
Articolo in rivista (Classe)

Label

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)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url

http://link.springer.com/article/10.1007%2Fs12210-013-0241-5 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

24 (literal)

Rivista

Rendiconti lincei. Scienze fisiche e naturali (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

9 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

3 (literal)

Note

ISI Web of Science (WOS) (literal)
Scopu (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

a C.R. ENEA Frascati, Via E. Fermi 45, Frascati, 00044 Rome, Italy b Dip. di Scienze e Tecnologie Chimiche, Università di Roma Tor Vergata, via della Ricerca Scientifica, 00133 Rome, Italy c Dip.di Chimica e Tecnologie Del Farmaco, Università 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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