- About this Journal ·
- Abstracting and Indexing ·
- Aims and Scope ·
- Article Processing Charges ·
- Articles in Press ·
- Author Guidelines ·
- Bibliographic Information ·
- Citations to this Journal ·
- Contact Information ·
- Editorial Board ·
- Editorial Workflow ·
- Free eTOC Alerts ·
- Publication Ethics ·
- Submit a Manuscript ·
- Subscription Information ·
- Table of Contents
ISRN Physical Chemistry
Volume 2014 (2014), Article ID 592850, 8 pages
MNDO and DFT Computational Study on the Mechanism of the Oxidation of 1,2-Diphenylhydrazine by Iodine
Department of Chemistry, Ahmadu Bello University, Zaria 810006, Nigeria
Received 3 February 2014; Accepted 2 March 2014; Published 27 March 2014
Academic Editors: W. B. Davis, H. Luo, H. Pal, and E. B. Starikov
Copyright © 2014 Gideon A. Shallangwa et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
- T. J. Kelly, R. Mukund, C. W. Spicer, and A. J. Pollack, “Concentrations and trapsformations of hazardous air pollutants,” Environmental Science and Technology, vol. 28, no. 8, pp. 378A–387A, 1994.
- IPCS, International Chemical Safety Card for 1,2-Diphenylhydrazine, International Programme for Chemical Safety WHO, Geneva, Switzerland, 1993.
- S. Ohnishi, M. Murata, S. Oikawa, Y. Hiraku, and S. Kawanishi, “Copper-dependent DNA damage induced by hydrazobenzene, an azobenzene metabolite,” Free Radical Research, vol. 32, no. 6, pp. 469–478, 2000.
- M. J. Zdilla, A. K. Verma, and S. C. Lee, “Reactivity of a sterically hindered Fe(II) thiolate dimer with amines and hydrazines,” Inorganic Chemistry, vol. 47, no. 23, pp. 11382–11390, 2008.
- S. Globig and K. J. Freundt, “Metabolism of hydrazobenzene in rat liver homogenate, Autumn Meeting of the Deutsche Gesellschaft Fuer Experimentelle Und Klinische PharmakologieUnd Toxikologie (German Society for Experimental and Clinical Pharmacology and Toxicology), Dresden, Germany, September 10-12, 1996,” Naunyn-Schmiedeberg's Archives of Pharmacology, vol. 354, no. 4, supplement 1, article R28, 1996.
- S. Globig, M. Killguss, and K. J. Freundt, “Metabolism of hydraobenzene and azobenzene in rat hepatocytes in primary culture, Autumn Meeting of the Deutsche Gesellschaft Fuer Experimentelle Und Klinische Pharmakologie Und Toxikologie (German Society for Experimental and Clinical Pharmacology and Toxicology), Dresden, Germany, September 10-12, 1996,” Naunyn-Schmiedeberg's Archives of Pharmacology, vol. 354, no. 4, supplement 1, article R419, 1996.
- A. Assi, S. Globig, and C. Koelbel, “Ph-dependent reaction types of hydrazobenzene in gastric juice and hydrous solution, 37th Spring Meeting of the German Society for Experimental and Clinical Pharmacology and Toxicology, Mainz, Germany, March 12-14, 1996,” Naunyn-Schmiedeberg's Archives of Pharmacology, vol. 353, no. 4 supplement, article R112, 1996.
- M. S. Khalil, N. Kelada, B. Sawyer, D. R. Zenz, P. Tata, and C. Lue-Hing, “Comparison of one-step acidic extraction versus two-step basic and acidic extraction procedures for semivolatile analysis of wastewater,” Water Environment Research, vol. 71, no. 3, pp. 348–354, 1999.
- R. B. Homer, R. D. Cannon, and S. S. B. Kim, “The oxidation of hydrazobenzene by oxygen catalyzed by CO(2MeOsalen) in methanol,” Bulletin of the Korean Chemical Society, vol. 6, no. 2, pp. 115–118, 1985.
- K. Ayub and T. Mahmood, “DFT studies of halogen bonding abilities of nitrobenzene with halogens and chlorofluorocarbons,” Journal of Chemical Society of Pakistan, vol. 35, no. 3, pp. 617–821, 2013.
- J. W. May and J. Halpern, “Kinetics of the oxidation of hydrazobenzeneby iodine and triiodide,” Canadian Journal of Chemistry, vol. 39, no. 6, pp. 1377–1385, 1961.
- B. J. P. Whalley, H. G. V. Evans, and C. A. Winkler, “The oxidation of hydrazobenzene by ammonium persulphate in acetonitrile-water solution,” Canadian Journal of Chemistry, vol. 34, no. 9, pp. 1154–1162, 1956.
- W. J. Zubyk, Dissertation [Ph.D. thesis], University of Delaware, 1957.
- K. J. Blackmore, N. Lal, J. W. Ziller, and A. F. Heyduk, “Catalytic reactivity of a zirconium(IV) redox-active ligand complex with 1,2-diphenylhydrazine,” Journal of the American Chemical Society, vol. 130, no. 9, pp. 2728–2729, 2008.
- R. A. Zarkesh, J. W. Ziller, and A. F. Heyduk, “Four-electron oxidative formation of aryl diazenes using a tantalum redox-active ligand complex,” Angewandte Chemie—International Edition, vol. 47, no. 25, pp. 4715–4718, 2008.
- T. X. T. Luu, P. Christensen, F. Duus, and T. N. Le, “Inorganic salt supported potassium permanganate promoted oxidation of aniline into azobenzene,” Journal of Chemistry, vol. 45, pp. 105–1110, 2007.
- J. W. Ochterski, “Thermochemistry in Gaussian,” Technical Support Information, gaussian.com, pp. 1-19, 2000.
- X.-Y. Cao, X.-M. Jiang, A. Kareem et al., “Iodination of irrigation water as a method of supplying iodine to a severely iodine-deficient population in Xinjiang, China,” The Lancet, vol. 344, no. 8915, pp. 107–110, 1994.
- S. M. Sultan, I. Z. Alzamil, A. M. Al-Hajjaji, S. A. Al-Tamrah, and A. M. A. Al-Rahman, “A kinetic study on the determination of hydrazine by iodine in sulphuric acid media,” Journal of Chemical Society of Pakistan, vol. 7, no. 2, pp. 93–99, 1985.
- K. J. Laidler, Physical Chemistry with Biological Applications, The Benjamin Cumming, San Francisco, Calif, USA, 1978.
- T. S. Rao and P. S. Dalvi, “Kinetics and mechanism of the rapid oxidation of hydrazine by iodine in weakly acidic solutions,” Proceeding Indian National Science Academy, vol. 56, no. 2, pp. 153–160, 1990.
- I. A. Funai and M. A. Blesa, “Kinetics and mechanism of the reaction of iodine with isonicotinoylhydrazide,” Canadian Journal of Chemistry, vol. 62, no. 12, pp. 2923–2928, 1984.
- M. S. Mshelia, F. Iyun, A. Uzairu, and S. Idris, “Kinetics and mechanism of the oxidation of hydrazine dihydrochloride by aqueous iodine,” Journal of American Science, vol. 6, no. 9, pp. 293–296, 2010.
- K. Mitteilung, “Kinetics of reaction between hydrazine and iodine solution,” Zeitschrift für Physikalische Chemie Nexie Folge, vol. 45, no. 5-6, pp. 378–382, 1965.
- S. E. King, J. N. Cooper, and R. D. Crawford, “Oxidation of hydrazine by iodine in aqueous perchloric acid,” Inorganic Chemistry, vol. 17, no. 11, pp. 3306–3307, 1978.
- D. A. Palmer and M. H. Lietzke, “The equilibria and kinetics of iodine hydrolysis,” Radiochim Acta, vol. 31, pp. 37–44, 1982.
- R. M. Smith and A. E. Martell, Critical Stability Constant, vol. 4, Plenum Press, New York, NY, USA, 1976.
- P. Bhatnagar, R. K. Mittal, and Y. K. Gupta, “Stoicheiometry, kinetics, and mechanism of the oxidation of hyponitrous acid by iodine in acetate buffers,” Journal of the Chemical Society, Dalton Transactions, no. 12, pp. 3669–3673, 1990.
- A. Mondal and R. Banerjee, “Kinetics and mechanism of uncatalyzed oxidation of hydrazine with superoxide coordinated to cobalt(III),” Indian Journal of Chemistry A, vol. 48, no. 5, pp. 645–649, 2009.
- D. C. Young, “Semi empirical methods,” in Computational Chemistry: A Practical Guide for Applying Techniques to Real World Problems, John Wiley & Sons, New York, NY, USA, 2002.
- Spartan User's Guide, version 3. 0, Wavefunction, 1993.
- K. Kahn and T. C. Bruice, “Transition-state and ground-state structures and their interaction with the active-site residues in catechol O-methyltransferase,” Journal of the American Chemical Society, vol. 122, no. 1, pp. 46–51, 2000.
- K. Kahn and P. A. Tipton, “Kinetics and mechanism of allantoin racemization,” Bioorganic Chemistry, vol. 28, no. 2, pp. 62–72, 2000.
- K. Kahn, “Theoretical study of intermediates in the urate oxidase reaction,” Bioorganic Chemistry, vol. 27, no. 5, pp. 351–362, 1999.
- J. J. P. Stewart, “Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements,” Journal of Molecular Modeling, vol. 13, no. 12, pp. 1173–1213, 2007.
- J. Marten, W. Seichter, E. Weber, and U. Böhme, “Crystalline packings of diketoarylhydrazones controlled by a methyl for trifluoromethyl structural change,” CrystEngComm, vol. 10, no. 5, pp. 541–547, 2008.
- J. Zhang and W. L. Hase, “Electronic structure theory study of the F− + CH3I → FCH3 + I− Potential Energy Surface,” The Journal of Physical Chemistry A, vol. 114, no. 36, pp. 9635–9643, 2010.
- F. Jensen, Introduction to Computational Chemistry, John Wiley & Sons, Chichester, UK, 1999.
- J. Castells, F. Geijo, and F. López-Calahorra, “The “formoin reaction” : a promising entry to carbohydrates from formaldehyde,” Tetrahedron Letters, vol. 21, no. 47, pp. 4517–4520, 1980.
- F. Jordan, “Theoretical studies on thiamin action, conformation of 2-1—hydroxethylthiamine,” Journal of American Chemical Society, vol. 98, pp. 808–813, 1976.
- W. Shin, D.-G. Oh, C.-H. Chae, and T.-S. Yoon, “Conformational analyses of thiamin-related compounds: a stereochemical model for thiamin catalysis,” Journal of the American Chemical Society, vol. 115, no. 26, pp. 12238–12250, 1993.
- A. A. Shaffer and S. G. Wierschke, “Comparison of computational methods applied to oxazole, thiazole, and other heterocyclic compounds,” Journal of Computational Chemistry, vol. 14, no. 1, pp. 75–88, 1993.
- F. T. Burling and B. M. Goldstein, “Computational studies of nonbonded sulfur-oxygen and selenium-oxygen interactions in the thiazole and selenazole nucleosides,” Journal of the American Chemical Society, vol. 114, no. 7, pp. 2313–2320, 1992.
- S. Kabirand and A. M. Sapse, “An ab initio study of the proton affinities of some heteroatomic rings: Imidazole, oxazole, and thiazole,” Journal of Computational Chemistry, vol. 12, no. 9, pp. 1142–1146, 1991.
- F. Mari, P. M. Lahti, and W. E. McEwen, “A theoretical study of the Wittig olefination reaction: MNDO-PM3 treatment of the Wittig half-reaction of unstabilized ylides with aldehydes,” Journal of the American Chemical Society, vol. 114, no. 3, pp. 813–821, 1992.
- T. Engel and P. Reid, Physical Chemistry, Pearson Prentice Hall, Upper saddle River, NJ, USA, 2006.
- R. P. Szajewski and G. M. Whitesides, “Rate constants and equilibrium constants for thiol-disulfide interchange reactions involving oxidized Glutathione,” Journal of the American Chemical Society, vol. 102, no. 6, pp. 2011–2026, 1980.