The germylation of simple aromatic hydrocarbons has been studied by two different techniques. The Fourier Transform Ion Cyclotron Resonance (FTICR) technique allowed the study of Me3Ge+ transfer equilibria between aromatics and H2O at 300 K. The ion-molecule reaction of [Me3Ge+ · arene] ions with selected neutrals are accounted for by a σ-complex species, retaining the primary ipso structure, where the germyl group and the former aromatic hydrogen are bound to the same tetrahedral carbon. The free energies of binding of Me3Ge+ to the selected aromatic compounds correlate linearly with the values of the corresponding Me3Si+ reaction with a slope of 0.93. The combined information from the FTICR and radiolytic technique has revealed a mechanistic pattern for the electrophilic aromatic substitution by Me3Ge+ that closely reproduces the corresponding Me3Si+ reaction, the major difference lying in the greater ease of detachment of Me3Ge+ by nucleophilic assistance.

Gas Phase Germylation of Simple Aromatics by Me3Ge+ Ions.” / Chiavarino, Barbara; Crestoni, Maria Elisa; Fornarini, Simonetta. - In: JOURNAL OF ORGANOMETALLIC CHEMISTRY. - ISSN 0022-328X. - STAMPA. - 545/546:(1997), pp. 53-59. [10.1016/S0022-328X(97)00318-5]

Gas Phase Germylation of Simple Aromatics by Me3Ge+ Ions.”

CHIAVARINO, Barbara;CRESTONI, Maria Elisa;FORNARINI, Simonetta
1997

Abstract

The germylation of simple aromatic hydrocarbons has been studied by two different techniques. The Fourier Transform Ion Cyclotron Resonance (FTICR) technique allowed the study of Me3Ge+ transfer equilibria between aromatics and H2O at 300 K. The ion-molecule reaction of [Me3Ge+ · arene] ions with selected neutrals are accounted for by a σ-complex species, retaining the primary ipso structure, where the germyl group and the former aromatic hydrogen are bound to the same tetrahedral carbon. The free energies of binding of Me3Ge+ to the selected aromatic compounds correlate linearly with the values of the corresponding Me3Si+ reaction with a slope of 0.93. The combined information from the FTICR and radiolytic technique has revealed a mechanistic pattern for the electrophilic aromatic substitution by Me3Ge+ that closely reproduces the corresponding Me3Si+ reaction, the major difference lying in the greater ease of detachment of Me3Ge+ by nucleophilic assistance.
File allegati a questo prodotto
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/247505
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 5
  • ???jsp.display-item.citation.isi??? 5
social impact