The C - C bond formation activated under negative electrospray ionization of an acetonitrile solution of 1,3,5-trinitrobenzene is reported. The solvent function is to provide a source of cyanide ion, a highly problematic reagent, which is found to attack the electron-deficient aromatic ring to form a covalently bound anionic complex (Meisenheimer complex). The structure of the complex is elucidated by means of collision induced dissociation mass spectrometry and IR multiple photon dissociation spectroscopy in the 'fingerprint' region. © 2013 American Society for Mass Spectrometry.

Cyanide–arene Meisenheimer complex generated in electrospray ionization mass spectrometry using acetonitrile as a solvent / Chiavarino, Barbara; P., Maitre; Fornarini, Simonetta; Crestoni, Maria Elisa. - In: JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY. - ISSN 1044-0305. - STAMPA. - 24:10(2013), pp. 1603-1607. [10.1007/s13361-013-0703-0]

Cyanide–arene Meisenheimer complex generated in electrospray ionization mass spectrometry using acetonitrile as a solvent

CHIAVARINO, Barbara;FORNARINI, Simonetta;CRESTONI, Maria Elisa
2013

Abstract

The C - C bond formation activated under negative electrospray ionization of an acetonitrile solution of 1,3,5-trinitrobenzene is reported. The solvent function is to provide a source of cyanide ion, a highly problematic reagent, which is found to attack the electron-deficient aromatic ring to form a covalently bound anionic complex (Meisenheimer complex). The structure of the complex is elucidated by means of collision induced dissociation mass spectrometry and IR multiple photon dissociation spectroscopy in the 'fingerprint' region. © 2013 American Society for Mass Spectrometry.
2013
IRMPD spectroscopy; Meisenheimer complexes; C – C coupling; Tandem mass spectrometry; Ab initio calculations
01 Pubblicazione su rivista::01a Articolo in rivista
Cyanide–arene Meisenheimer complex generated in electrospray ionization mass spectrometry using acetonitrile as a solvent / Chiavarino, Barbara; P., Maitre; Fornarini, Simonetta; Crestoni, Maria Elisa. - In: JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY. - ISSN 1044-0305. - STAMPA. - 24:10(2013), pp. 1603-1607. [10.1007/s13361-013-0703-0]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/525594
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