Electrochemical Studies of Protonation Reaction of Anion Radicals of Some Dinitroaromatics in Dichloromethane

Farzana Hanif; Ghazala Yasmeen; Suryyia Manzoor; Muhammad Aamir

doi:10.14233/ajchem.2015.18291

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Issue Published : April 27, 2015

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

Electrochemical Studies of Protonation Reaction of Anion Radicals of Some Dinitroaromatics in Dichloromethane

https://doi.org/10.14233/ajchem.2015.18291

Farzana Hanif

Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan

Ghazala Yasmeen

Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan

Suryyia Manzoor

Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan

Muhammad Aamir

Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan

Corresponding Author(s) : Ghazala Yasmeen

ghazala31pk@yahoo.com

Asian Journal of Chemistry, Vol. 27 No. 8 (2015): Vol 27 Issue 8
Article Published : April 27, 2015

Abstract

Protonation of anion radicals of 1,2-,1,3- and 1,4-dinitrobenzenes in dichloromethane in the temperature range 0, 5, 10 and 15 °C has been investigated by cyclic voltammetric method. Glassy carbon electrode and hanging mercury drop electrode are used as working electrodes. Benzoic acid and salicylic acid are used as protonating agents. Homogeneous rate constant is calculated by using Nicholson and Shain equation. The position of nucleophilic attack in dinitrobenzenes has been investigated by calculation of charge densities using MNDO and SCF-UHF molecular orbital methods. The heterogeneous rate constant k_s,h for the first reduction process in dinitrobenzenes is determined by digital simulation of the cyclic voltammograms.

Keywords

Anion radicals Cyclic voltammetry Protonation reactions Dinitrobenzene Dichloromethane

Hanif, F., Yasmeen, G., Manzoor, S., & Aamir, M. (2015). Electrochemical Studies of Protonation Reaction of Anion Radicals of Some Dinitroaromatics in Dichloromethane. Asian Journal of Chemistry, 27(8), 2924–2932. https://doi.org/10.14233/ajchem.2015.18291

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References

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References

A.S. Mendkovich, M.A. Syroeshkin, L.V. Mikhalchenko, M.N. Mikhailov, A. Rusakov and V.P. Gultyai, Int. J. Electrochem., 1 (2011); doi:10.4061/2011/346043.

A.S. Mendkovich, M.A. Syroeshkin, L.V. Mikhalchenko, A.I. Rusakov and V.P. Gultyai, Russ. Chem. Bull., 57, 1492 (2008); doi:10.1007/s11172-008-0193-6.

E. Steudel, J. Posdorfer and R.N. Schindler, Electrochim. Acta, 40, 1587 (1995); doi:10.1016/0013-4686(95)00102-K.

M.A. Syroeshkin, A.S. Mendkovich, L.V. Mikhalchenko, A.I. Rusakov and V.P. Gul'tyai, Mendeleev Commun., 19, 258 (2009); doi:10.1016/j.mencom.2009.09.008.

M.A. Syroeshkin, A.S. Mendkovich, L.V. Mikhal’chenko, A.I. Rusakov and V.P. Gul’tyai, Russ. Chem. Bull., 58, 468 (2009); doi:10.1007/s11172-010-0034-2.

V. Mikhalchenko, A.S. Mendkovich, M.A. Syroeshkin and V.P. Gul'tyai, Mendeleev Commun., 19, 96 (2009); doi:10.1016/j.mencom.2009.03.015.

M.A. Syroeshkin, M.N. Mikhailov, A.S. Mendkovich and A.I. Rusakov, Russ. Chem. Bull., 58, 41 (2009); doi:10.1007/s11172-009-0006-6.

A.S. Mendkovich, M.A. Syroeshkin, L.V. Mikhalchenko, A.I. Rusakov and V.P. Gultyai, Russ. Chem. Bull., 57, 1492 (2008); doi:10.1007/s11172-008-0193-6.

L.J. Núñez-Vergara, J.A. Squella, C. Olea-Azar, S. Bollo, P.A. Navarrete-Encina and J.C. Sturm, Electrochim. Acta, 45, 3555 (2000); doi:10.1016/S0013-4686(00)00477-1.

D.H. Evans, Chem. Rev., 108, 2113 (2008); doi:10.1021/cr068066l.

N.G. Tsierkezos, J. Solution Chem., 36, 289 (2007); doi:10.1007/s10953-006-9119-9.

N.A. Macías-Ruvalcaba, J.P. Telo and D.H. Evans, J. Electroanal. Chem., 600, 294 (2007); doi:10.1016/j.jelechem.2006.10.003.

D.S. Silvester, A.J. Wain, L. Aldous, C. Hardacre and R.G. Compton, J. Electroanal. Chem., 596, 131 (2006); doi:10.1016/j.jelechem.2006.07.028.

M. Mohammad and M.J. Aslam, J. Chem. Soc. Pak., 33, 12 (2011).

D.D. Perrin, Purification of Laboratory Chemicals, Pergamon Press, Oxford/New York, edn 1 (1974).

Operating and Service Manual, Model 174A Polarographic Analyzer, EG & G Princeton Applied Research, New Jersey, USA.

J.W. Ross, R.D. DeMars and I. Shain, Anal. Chem., 28, 1768 (1956); doi:10.1021/ac60119a039.

D.O. Wipf and R.M. Wightman, Anal. Chem., 62, 98 (1990); doi:10.1021/ac00201a002.

R.S. Nicholson and I. Shain, Anal. Chem., 36, 706 (1964); doi:10.1021/ac60210a007.

D.T. Sawyer, Experimental Electrochemistry for Chemists, John Wiley & Sons, p. 170 (1974).

C. Reichardt, Solvents and Solvent Effect in Organic Chemistry, Ch. 7, VCH Publishers, Cambridge (1988).

N.E. Miller, M.C. Wander and R.J. Cave, J. Phys. Chem., 103, 1084 (1999); doi:10.1021/jp983171n.

D.H. Evans, Chem. Rev., 108, 2113 (2008); doi:10.1021/cr068066l.

Z.V. Todres, Ion-Radical Organic Chemistry: Principles and Applications, CRC Press, Taylor & Francis Group, Boca Raton, Fl., USA, edn 2 (2009).

T.T.T. Li and M.J. Weaver, J. Am. Chem. Soc., 106, 6107 (1984); doi:10.1021/ja00332a073.

F. Booth, J. Chem. Phys., 19, 391 (1951); doi:10.1063/1.1748233.

J.M. Hale, in ed.: N.S. Hush, Reactions of Molecules at Electrodes, Wiley Interscience, New York (1970).

D.R. Lide, Hand book of Organic Solvents, CRC Press Boca Roton, Ann Arbor, London, p. 142 (1995).

A.J. Bard and L.R. Faulkner, Electrochemical Methods, John Wiley & Sons, New York, edn 2 (2001).

D. Britz, Digital Simulation in Electrochemistry, Springer, Berlin (1981).

D.K. Gosser and P.H. Rieger, Anal. Chem., 60, 1159 (1988); doi:10.1021/ac00162a014.

D.K. Gosser Jr., Cyclic Voltammetry, VCH, New York and Weinheim, Germany, p. 275 (1993).

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Electrochemical Studies of Protonation Reaction of Anion Radicals of Some Dinitroaromatics in Dichloromethane

Corresponding Author(s) : Ghazala Yasmeen

Abstract

Keywords

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