Communication: vibrational study of a benzyl carbanion: deprotonated 2,4-dinitrotoluene.

Maria Elisa Crestoni, Barbara Chiavarino, Vincent Steinmetz, Simonetta Fornarini

Dipartimento di Chimica e Tecnologie del Farmaco, Università di Roma La Sapienza, P. le A. Moro 5, I-00185 Roma, Italy. mariaelisa.crestoni@uniroma1.it

The Journal of chemical physics 2012 Nov 14

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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.

Citation

Maria Elisa Crestoni, Barbara Chiavarino, Vincent Steinmetz, Simonetta Fornarini. Communication: vibrational study of a benzyl carbanion: deprotonated 2,4-dinitrotoluene. The Journal of chemical physics. 2012 Nov 14;137(18):181101