The bare deprotonated 2,4-dinitrotoluene [DNT-H]− anion, formed by electrospray ionization and trapped in a Paul ion-trap, has been investigated by IR multiple photon dissociation (IRMPD) spectroscopy and quantum chemical calculations at the B3LYP/6-311++G** level. IRMPD spectra were recorded in the 950–1800 cm−1 fingerprint range and interpreted by comparison with the calculated IR absorption spectra for different low-lying isomers. The sampled [DNT-H]− species is found to involve deprotonation at the methyl group, yielding a benzyl carbanion 1, previously described as an amine complex in solution and here characterized by vibrational spectroscopy as an unperturbed gaseous species. Anion 1 is the most stable species among [DNT-H]− isomers. © 2012 American Institute of Physics.

Vibrational study of a benzyl carbanion: deprotonated 2,4-dinitrotoluene / Crestoni, Maria Elisa; Chiavarino, Barbara; V., Steinmetz; Fornarini, Simonetta. - In: THE JOURNAL OF CHEMICAL PHYSICS. - ISSN 0021-9606. - STAMPA. - 137:(2012), pp. 181101-1-181101-4. [10.1063/1.4767393]

Vibrational study of a benzyl carbanion: deprotonated 2,4-dinitrotoluene

CRESTONI, Maria Elisa;CHIAVARINO, Barbara;FORNARINI, Simonetta
2012

Abstract

The bare deprotonated 2,4-dinitrotoluene [DNT-H]− anion, formed by electrospray ionization and trapped in a Paul ion-trap, has been investigated by IR multiple photon dissociation (IRMPD) spectroscopy and quantum chemical calculations at the B3LYP/6-311++G** level. IRMPD spectra were recorded in the 950–1800 cm−1 fingerprint range and interpreted by comparison with the calculated IR absorption spectra for different low-lying isomers. The sampled [DNT-H]− species is found to involve deprotonation at the methyl group, yielding a benzyl carbanion 1, previously described as an amine complex in solution and here characterized by vibrational spectroscopy as an unperturbed gaseous species. Anion 1 is the most stable species among [DNT-H]− isomers. © 2012 American Institute of Physics.
2012
IRMPD spectroscopy; Nitroaromatics; Mass spectrometry; Ab initio calculations; benzyl anion
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Vibrational study of a benzyl carbanion: deprotonated 2,4-dinitrotoluene / Crestoni, Maria Elisa; Chiavarino, Barbara; V., Steinmetz; Fornarini, Simonetta. - In: THE JOURNAL OF CHEMICAL PHYSICS. - ISSN 0021-9606. - STAMPA. - 137:(2012), pp. 181101-1-181101-4. [10.1063/1.4767393]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/491992
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