Observation of replacement of carbon in benzene with nitrogen in a low-temperature plasma

Scientific Reports

Volumn 3, Issue , 2013, Pages

  Zhang, Zhiping ^a   Gong, Xiaoyun ^a   Zhang, Sichun ^a   Yang, Haijun ^a   Shi, Youmin ^a   Yang, Chengdui ^b   Zhang, Xinrong ^b   Xiong, Xingchuang ^c   Fang, Xiang ^c   Ouyang, Zheng ^d  

^a XI'AN SHIYOU UNIVERSITY   (China)

^b TSINGHUA UNIVERSITY   (China)

^c NATIONAL INSTITUTE OF METROLOGY   (China)

^d PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84890689623     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep03481     Document Type: Article

References (24)

1. Di Stefano, M. et al. Experimental and theoretical investigation of the production of cations containing C-N bonds in the reaction of benzene with atomic nitrogen ions. J. Chem. Phys. 119, 1978-1985 (2003).
2. Skokov, S. & Wheeler, R. A. Oxidative aromatic substitutions: Hartree-Fock/density functional and ab initio molecular orbital studies of benzene and toluene nitrosation. J Phys. Chem. A 103, 4261-4269 (1999). (Pubitemid 129570907)
3. Giordana, A. et al. The reaction of N2O with phenylium ions C6(H,D)5 1: An integrated experimental and theoretical mechanistic study. J. Chem. Phys. 131, (2009).
4. Di Stefano, M., Rosi, M., Sgamellotti, A. & Negri, F. Reactions of N1 ions with benzene: a theoretical study on the C6NH6 1 potential energy surface. Chem. Phys. 302, 295-308 (2004).
5. Ascenzi, D., Franceschi, P., Freegarde, T. G. M., Tosi, P. & Bassi, D. C-N bond formation in the reaction of nitrogen ions N1 with benzene molecules. Chem. Phys. Lett. 346, 35-40 (2001). (Pubitemid 33396311)
6. Smith, D., Wang, T. S. & Spanel, P. A SIFT study of the reactions ofH2ONO1 ions with several types of organic molecules. Int. J. Mass Spectrom. 230, 1-9 (2003).
7. Niwa, S. et al. A one-step conversion of benzene to phenol with a palladium membrane. Science 295, 105-107 (2002). (Pubitemid 34052354)
8. Ascenzi, D., Franceschi, P., Guella, G.&Tosi, P. Phenol production in benzene/air plasmas at atmospheric pressure. Role of radical and ionic routes. J. Phys. Chem. A 110, 7841-7847 (2006). (Pubitemid 44131323)
9. Rosso, J. A., Bertolotti, S. G., Braun, A. M., Martire, D. O. & Gonzalez, M. C. Reactions of carbon dioxide radical anion with substituted benzenes. J. Phys. Org. Chem. 14, 300-309 (2001). (Pubitemid 32445166)
10. Srinivas, R., Hrusak, J., Sulzle, D., Bohme, D. K. & Schwarz, H. Experimental and theoretical characterization of isomeric adduct ions of Si.1 and benzene and their neutral counterparts. J. Am. Chem. Soc. 114, 2802-2806 (1992).
11. Allen, W. N. & Lampe, F. W. Ion-molecule reaction in monosilane-benzene mixtures-long-lived collision complexes. J. Am. Chem. Soc. 99, 2943-2948 (1977).
12. Keck, H., Kuchen, W., Terlouw, J. K. & Tommes, P. Does phenylphosphinidene exist? Mass spectrometric generation and characterization of Ph-P. Phosphorus, Sulfur Silicon Relat. Elem. 149, 23-28 (1999).
13. Muedas, C. A., Schroder, D., Sulzle, D. & Schwarz, H. Insertion of phosphorous into the C-C bond of benzene as observed by collision-mass spectrometry. J. Am. Chem. Soc. 114, 7582-7584 (1992).
14. Li, G., Li, X., Ouyang, Z. & Cooks, R. G. Carbon-Carbon Bond Activation in Saturated Hydrocarbons by Field-Assisted Nitrogen Fixation. Angew. Chem. Int. Edit. 52, 1040-1043 (2013).
15. Na, N., Xia, Y., Zhu, Z., Zhang, X. & Cooks, R. G. Birch reduction of benzene in a low-temperature plasma. Angew. Chem. Int. Edit. 48, 2017-2019 (2009).
16. Badjagbo, K., Picard, P., Moore, S. & Sauvé, S. Direct atmospheric pressure chemical ionization-tandem mass spectrometry for the continuous real-time trace analysis of benzene, toluene, ethylbenzene, and xylenes in ambient air. J. Am. Soc. Mass Spectrom. 20, 829-836 (2009).
17. Turney, T. A. & Wright, G. A. Nitrous acid and nitrosation. Chem. Rev. 59, 497-513 (1959).
18. Williams, D. L. H. in Advances in Physical Organic Chemistry Vol.Volume 19 (eds Gold, V. & Bethell, D.) 381-428 (Academic Press, 1983).
19. Reents, W. D. & Freiser, B. S. Gas-phase nitrosation of benzene. Implications for solution electrophilic aromatic substitution reactions. J. Am. Chem. Soc. 102, 271-276 (1980).
20. Hubig, S. M. & Kochi, J. K. Direct observation of the wheland intermediate in electrophilic aromatic substitution. Reversible formation of nitrosoarenium cations. J. Am. Chem. Soc. 122, 8279-8288 (2000).
21. Gwaltney, S. R., Rosokha, S. V., Head-Gordon, M. & Kochi, J. K. Charge-transfer mechanism for wlectrophilic aromatic nitration and nitrosation via the convergence of (ab Initio) molecular-orbital and Marcus2Hush theories with experiments. J. Am. Chem. Soc. 125, 3273-3283 (2003). (Pubitemid 36519122)
22. Chiavarino, B. et al. p-complex structure of gaseous benzene2NOcations assayed by IR multiple photon dissociation spectroscopy. J. Am. Chem. Soc. 128, 12553-12561 (2006). (Pubitemid 44476646)
23. Cacace, F., Attina, M., De Petris, G. & Speranza, M. Protonated nitric acid. Structure and relative stability of isomeric H2NO3 1 ions in the gas phase. J. Am. Chem. Soc. 112, 1014-1018 (1990). (Pubitemid 20127045)
24. De Petris, G., Di Marzio, A. & Grandinetti, F. H2NO2 1 ions in the gas phase: a mass spectrometric and post-SCF ab initio study. J. Phys. Chem. 95, 9782-9787 (1991).