Debromination of Bromobenzene Induced by Hydrated Electrons in Aqueous Solution

Haixia Yuan; Huxiang Pan; Jin Shi; Hongjing Li; Wenbo Dong

doi:10.14233/ajchem.2014.16068

Issue

Vol. 26 No. 14 (2014): Vol 26 Issue 14

Issue Published : July 5, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Debromination of Bromobenzene Induced by Hydrated Electrons in Aqueous Solution

https://doi.org/10.14233/ajchem.2014.16068

Haixia Yuan

Shanghai Key Laboratory of Atmospheric Particle Pollution and Prevention, Department of Environmental Science and Engineering, Fudan University, Shanghai 200433, P.R. China; Institutes of Naval Medicine, Shanghai 200433, P.R. China

Huxiang Pan

Institutes of Naval Medicine, Shanghai 200433, P.R. China

Jin Shi

Shanghai Key Laboratory of Atmospheric Particle Pollution and Prevention, Department of Environmental Science and Engineering, Fudan University, Shanghai 200433, P.R. China

Hongjing Li

Shanghai Key Laboratory of Atmospheric Particle Pollution and Prevention, Department of Environmental Science and Engineering, Fudan University, Shanghai 200433, P.R. China

Wenbo Dong

Shanghai Key Laboratory of Atmospheric Particle Pollution and Prevention, Department of Environmental Science and Engineering, Fudan University, Shanghai 200433, P.R. China

Corresponding Author(s) : Hongjing Li

lihongjing@fudan.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 14 (2014): Vol 26 Issue 14
Article Published : July 5, 2014

Abstract

The nanosecond laser flash photolysis (LFP) experiments were adopted to investigate the kinetics and mechanisms of the reaction between bromobenzene and hydrated electrons (e_aq) in aqueous solution. The results showed that the rate constants of first-order and second-order reaction were 6.3 × 10⁵ s^-1 and 1.7 × 10¹⁰ L mol^-1 s^-1, respectively. The final products were biphenyl, bromobiphenyl and Br^-, which determined by gas chromatography-mass spectrometry (GC-MS) and ion chromatography (IC). The optimal structure of bromobenzene anion radicals, the bond lengths and bond angles were calculated and analyzed by time-dependent density functional theory (TD-DFT)-UB3LYP method and the primary absorption peaks of the anion radicals lied in the ranges of 250-600 nm. The main reaction pathway was speculated that bromobenzene molecules generated unstable anion radicals when attacked by hydrated electrons and then the molecules debrominated to generate benzene radicals and Br^-.

Keywords

Laser flash photolysis Hydrated electrons Bromobenzene Anion radicals

Yuan, H., Pan, H., Shi, J., Li, H., & Dong, W. (2014). Debromination of Bromobenzene Induced by Hydrated Electrons in Aqueous Solution. Asian Journal of Chemistry, 26(14), 4211–4214. https://doi.org/10.14233/ajchem.2014.16068

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References

W.H. Ding, K.M. Aldous, R.G. Briggs, H. Valente, D.R. Hilker, S. Connor and G.A. Eadon, Chemosphere, 25, 675 (1992); doi:10.1016/0045-6535(92)90430-Y.
E.M. Boyd, K. Killham, J. Wright, S. Rumford, M. Hetheridge, R. Cumming and A.A. Meharg, Chemosphere, 35, 1967 (1997); doi:10.1016/S0045-6535(97)00271-3.
S. Masunaga, Y. Yonezawa and Y. Urushigawa, Water Res., 25, 275 (1991); doi:10.1016/0043-1354(91)90007-D.
B.G. Oliver, Adv. Chem., 216, 471 (1987); doi:10.1021/ba-1987-0216.ch014.
M. Wang and K.C. Jones, J. Agric. Food Chem., 42, 2322 (1994); doi:10.1021/jf00046a046.
E. Halfon and M.G. Reggiani, Environ. Sci. Technol., 20, 1173 (1986); doi:10.1021/es00153a014.
M. Julliard, M. Chanon and A. Galadi, J. Photochem. Photobiol. Chem., 83, 107 (1994); doi:10.1016/1010-6030(94)03811-2.
H. Mohan and K.-D. Asmus, J. Chem. Soc. Perkin Trans. II, 1795 (1987); doi:10.1039/p29870001795.
D.B. Naik and H. Mohan, Radiat. Phys. Chem., 73, 218 (2005); doi:10.1016/j.radphyschem.2004.08.010.
J. Lichtscheidl and N. Getoff, Int. J. Radiat. Phys. Chem., 8, 661 (1976); doi:10.1016/0020-7055(76)90037-1.
S. Higashino, A. Saeki, K. Okamoto, S. Tagawa and T. Kozawa, J. Phys. Chem. A, 114, 8069 (2010); doi:10.1021/jp102828g.
H.X. Yuan, H.X. Pan, Y.L. Wu, J.-F. Zhao and W.-B. Dong, Acta Phys. Chim. Sin., 28, 957 (2012); doi:10.3866/PKU.WHXB201202203.
Y. Mori, H. Shinoda, T. Nakano and T. Kitagawa, J. Phys. Chem. A, 106, 11743 (2002); doi:10.1021/jp020332l.
L. Huang, W.B. Dong and H.Q. Hou, Chem. Phys. Lett., 436, 124 (2007); doi:10.1016/j.cplett.2007.01.037.
M. Wu, W. Shi, Y. Wang, Z. Jiao, J. Wang, G. Ding and J. Fu, Environ. Technol., 30, 191 (2009); doi:10.1080/09593330802468954.
J.M. Saveant, J. Phys. Chem., 98, 3716 (1994); doi:10.1021/j100065a029.
M. Arun Prasad and M.V. Sangaranarayanan, Tetrahedron, 61, 3755 (2005); doi:10.1016/j.tet.2005.02.011.
E. Taskinen, Struct. Chem., 11, 293 (2000); doi:10.1023/A:1009286209912.
I.V. Beregovaya and L.N. Shchegoleva, Chem. Phys. Lett., 348, 501 (2001); doi:10.1016/S0009-2614(01)01171-X.
K.D. Jordan, J.A. Michejda and P.D. Burrow, J. Am. Chem. Soc., 98, 7189 (1976); doi:10.1021/ja00439a014.

References

W.H. Ding, K.M. Aldous, R.G. Briggs, H. Valente, D.R. Hilker, S. Connor and G.A. Eadon, Chemosphere, 25, 675 (1992); doi:10.1016/0045-6535(92)90430-Y.

E.M. Boyd, K. Killham, J. Wright, S. Rumford, M. Hetheridge, R. Cumming and A.A. Meharg, Chemosphere, 35, 1967 (1997); doi:10.1016/S0045-6535(97)00271-3.

S. Masunaga, Y. Yonezawa and Y. Urushigawa, Water Res., 25, 275 (1991); doi:10.1016/0043-1354(91)90007-D.

B.G. Oliver, Adv. Chem., 216, 471 (1987); doi:10.1021/ba-1987-0216.ch014.

M. Wang and K.C. Jones, J. Agric. Food Chem., 42, 2322 (1994); doi:10.1021/jf00046a046.

E. Halfon and M.G. Reggiani, Environ. Sci. Technol., 20, 1173 (1986); doi:10.1021/es00153a014.

M. Julliard, M. Chanon and A. Galadi, J. Photochem. Photobiol. Chem., 83, 107 (1994); doi:10.1016/1010-6030(94)03811-2.

H. Mohan and K.-D. Asmus, J. Chem. Soc. Perkin Trans. II, 1795 (1987); doi:10.1039/p29870001795.

D.B. Naik and H. Mohan, Radiat. Phys. Chem., 73, 218 (2005); doi:10.1016/j.radphyschem.2004.08.010.

J. Lichtscheidl and N. Getoff, Int. J. Radiat. Phys. Chem., 8, 661 (1976); doi:10.1016/0020-7055(76)90037-1.

S. Higashino, A. Saeki, K. Okamoto, S. Tagawa and T. Kozawa, J. Phys. Chem. A, 114, 8069 (2010); doi:10.1021/jp102828g.

H.X. Yuan, H.X. Pan, Y.L. Wu, J.-F. Zhao and W.-B. Dong, Acta Phys. Chim. Sin., 28, 957 (2012); doi:10.3866/PKU.WHXB201202203.

Y. Mori, H. Shinoda, T. Nakano and T. Kitagawa, J. Phys. Chem. A, 106, 11743 (2002); doi:10.1021/jp020332l.

L. Huang, W.B. Dong and H.Q. Hou, Chem. Phys. Lett., 436, 124 (2007); doi:10.1016/j.cplett.2007.01.037.

M. Wu, W. Shi, Y. Wang, Z. Jiao, J. Wang, G. Ding and J. Fu, Environ. Technol., 30, 191 (2009); doi:10.1080/09593330802468954.

J.M. Saveant, J. Phys. Chem., 98, 3716 (1994); doi:10.1021/j100065a029.

M. Arun Prasad and M.V. Sangaranarayanan, Tetrahedron, 61, 3755 (2005); doi:10.1016/j.tet.2005.02.011.

E. Taskinen, Struct. Chem., 11, 293 (2000); doi:10.1023/A:1009286209912.

I.V. Beregovaya and L.N. Shchegoleva, Chem. Phys. Lett., 348, 501 (2001); doi:10.1016/S0009-2614(01)01171-X.

K.D. Jordan, J.A. Michejda and P.D. Burrow, J. Am. Chem. Soc., 98, 7189 (1976); doi:10.1021/ja00439a014.

Issue

Vol. 26 No. 14 (2014): Vol 26 Issue 14

Debromination of Bromobenzene Induced by Hydrated Electrons in Aqueous Solution

Corresponding Author(s) : Hongjing Li

Abstract

Keywords

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