Competition between electron-donor and electron-acceptor substituents in nitrotoluene isomers: a photoelectron spectroscopy and ab initio investigation (Articolo in rivista)

Type
Label
  • Competition between electron-donor and electron-acceptor substituents in nitrotoluene isomers: a photoelectron spectroscopy and ab initio investigation (Articolo in rivista) (literal)
Anno
  • 2014-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1039/c3ra45705b (literal)
Alternative label
  • F. Rondino, D. Catone, G. Mattioli, A. Amore Bonapasta, P. Bolognesi,A. R. Casavola, M. Coreno, P. O'Keeffe and L. Avaldi (2014)
    Competition between electron-donor and electron-acceptor substituents in nitrotoluene isomers: a photoelectron spectroscopy and ab initio investigation
    in RSC advances
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • F. Rondino, D. Catone, G. Mattioli, A. Amore Bonapasta, P. Bolognesi,A. R. Casavola, M. Coreno, P. O'Keeffe and L. Avaldi (literal)
Pagina inizio
  • 5272 (literal)
Pagina fine
  • 5282 (literal)
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  • il modulo MD.P03.026.001 dal 2014 passa dall'istituto IMIP all' ISM (literal)
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  • 4 (literal)
Rivista
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  • 10 (literal)
Note
  • ISI Web of Science (WOS) (literal)
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  • ENEA Centro Ricerche di Frascati, Unità Tecnica Sviluppo di Applicazioni delle Radiazioni, Via E. Fermi 45, I-00044 Frascati, RM, Italy Istituto di Struttura della Materia del CNR, Via del Fosso del Cavaliere 100, I-00133 Roma, Italy Istituto di Struttura della Materia del CNR, Via Salaria Km 29.300, I-00015 Monterotondo Stazione, RM, Italy. Istituto di Metodologie Inorganiche e dei Plasmi del CNR, Via Salaria Km 29.300, I-00015 Monterotondo Stazione, RM, Italy (literal)
Titolo
  • Competition between electron-donor and electron-acceptor substituents in nitrotoluene isomers: a photoelectron spectroscopy and ab initio investigation (literal)
Abstract
  • We present an investigation of the close relationship between chemical structure, physical properties and reactivity of the three nitrotoluene isomers: a joint experimental and theoretical study, based on X-ray photoelectron spectroscopy (XPS) measurements and ab initio calculations, addressing the complex interplay between the competing electron-donor and electron-acceptor effects of the nitro- and methyl-substituents on the chemical properties of the nitrotoluene isomers. As the main results of the investigation we: (i) point out that accurate ab initio calculations play a key role in the complete assignment of photoemission measurements, as well as in the estimate of proton affinities in the case of all the eligible sites; (ii) revisit, at a more quantitative level, textbook models based on inductive and resonant effects of different substituents of the aromatic ring, as well as on the hyper-conjugative connection of the methyl group to the pi-conjugated system; (iii) provide an accurate analysis of correlation patterns between calculated proton affinities and core-ionization energies, which represent a powerful tool, capable of predicting site-specific reactivities of polysubstituted molecules in the case of electrophilic aromatic substitution reactions. (literal)
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