Electrochemical investigations on 5-methyl-4- 4|-substituted phenylhydrazono - 2- 5-thioxo-4,5- dihydro-[1,3,4]oxadiazole-2-ylmethyl -2,4- dihydro-pyrazol-3-ones

Year 2014, Volume: 42 Issue: 2, 201 - 218, 01.06.2014

Krishna Naik Aluru Raghavendra Guru Prasad Yadatai Narasimha Spoorthy Lakshmana Rao Krishna Rao Ravindranath

Abstract

The electrochemical investigations on 5-methyl-4- 4|-substitute phenylhydrazono - 2- 5-thioxo-4,5-dihydro-[1,3,4] oxadiazole-2-ylmethyl -2,4-dihydro-pyrazol-3-ones having substitutions namely -H, -CH3 , -OCH3 , -OC2H5, -Cl, -Br were carried out in Briton-Robinson buffer solutions. Investigations were carried to study the effect of pH, height of mercury column, effect of substituents based on which reduction mechanism was proposed in acid as well as in basic medium. The compounds under investigation exhibit a well defined single wave in the buffer solutions of pH 1.1-7.1 and two waves in solutions of pH 8.1-10.1 in polarographic studies at DME. In cyclic voltammetric studies at HMDE one cathodic peak in lower scan rates and two cathodic peaks in higher scan rates were obtained along with an inverted peak in solutions of pH 2.1-7.1. Cyclic voltammetric studies at MCPE leads to one cathodic peak in solu- tions of pH 2.1-7.1 and two cathodic peaks in pH range of 8.1-10.1 along with an anodic peak in solutions of pH 2.1-7.1. A detailed comparison of results obtained in polarographic studies with those obtained in cyclic voltammetry at HDME and MCPE were presented in the studies.

Keywords

Pyrazol-3-ones, polarography, cyclic voltammetry, DME, MCPE, reduction mechanism

5-metil-4- 4I-fenil hidrazon -2- 5-tiyooko- 4,5-dihidro-[1,3,4]oksadiazol-2-ilmetil -2,4- dihidro-pirazol-3-on üzerine elektrokimyasal incelemeler

Abstract

metil-4- 4-fenilhidrazon -2- 5-tiyookso-4,5-dihidro-[1,3,4]oksadiazol-2-ilmetil -2,4-dihidro-pirazol-3-,-H,-CH3, -OCH3, -OC2H5, -Cl, -Br sübstitüe olmuş moleküller üzerinde elektrokimyasal incelemeler gerçekleştirilmiştir. Polarografik araştırmalar, hem asidik hem de bazik ortamlarda önerilen indirgenme mekanizmalarına dayalı pH etkisi, cıva kolon yüksekliği etkisi ve sübstitüsyon etkisi çalışmalarıyla gerçekleştirilmiştir. Polarografik çalışmalarda elde edilen sonuçlar, siklik voltametrede modifiye karbon pasta elektrot MCPE ve damlayan cıva elektrotu DME kullanılarak elde edilen sonuçlarla karşılaştırılmıştır

Keywords

Pirazol-3-on, polarografi, siklik voltametri, DME, MCPE, indirgenme mekanizması

References

• C.R. Biju, K. Ilango, M. Prathap, K. Renka, Design and Microwave-assisted Synthesis of 1,3,4-Oxadiazole Derivatives for Analgesic and Anti-inflammatory Activity, J Young Pharm., 4 (2012) 33–37.
• BN. Prasanna Kumar, KN. Mohana, L. Mallesha, KP. Harish, Synthesis and In Vitro Antimicrobial Evaluation of New 1,3,4-Oxadiazoles Bearing 5-Chloro-2-methoxyphenyl Moiety, International Journal of Medicinal Chemistry, 2013 (2013) 1-6.
• D. Kumar, S. Sundaree, EO. Johnson, K. Shah, An efficient synthesis and biological study of novel indolyl-1,3,4-oxadiazoles as potent anticancer agents, Bioorganic and Medicinal Chemistry Letters, 19 (2009) 4492–4494.
• Z.H. Luo, S.Y. He, B.Q. Chen, Y.P. Shi, Y.M. Liu, C.W. Li, Q.S. Wang, Synthesis and in vitro antitumor activity of 1,3,4-oxadiazole derivatives based on benzisoselenazolone, Chem. Pharm. Bull. (Tokyo), 60 (2012)887-91.
• S. Tabatabai, F. Ahmadi, Research in Pharmaceutical Sciences, 13th Iranian Pharmaceutical Sciences Congress, 7 (2012) S598.
• S.R. Pattan, P.A. Rabara, J.S. Pattan, A.A. Bukitagar, V.S. Wakale, D.S. Musmad, Synthesis and evaluation of some novel substituted 1,3,4-oxadiazole and pyrazole derivatives for antitubercular activity, Indian Journal of Chemistry, 48B (2009) 1453-1456.
• N. Das, A. Verma, P.K. Shrivastava, S.K. Shrivastava, Synthesis and biological evaluation of some new aryl pyrazol-3-one derivatives as potential hypoglycemic agents, Indian Journal of Chemistry, , 47B (2008) 1555-1558.
• IM. Abdou, A M. Saleh, HF. Zohdi, Synthesis and Antitumor Activity of 5-Trifluoromethyl- 2,4dihydropyrazol 3-oneNucleosides, Molecules, 9 (2004) 109–116.
• K.B. Umesha, M.L. Rai, M.A.H. Nayaka, Antioxidant and Antimicrobial Activity of 5-methyl-2-(5-methyl- 1,3-diphenyl-1H-pyrazole-4-carbonyl)-2,4-dihydro- pyrazol-3-one, Int J Biomed Sci.,5 (2009) 359–368.
• C. Sharma, B. Thadhaney, G. Pemawat, G.L. Talesara, Synthesis of some novel ethoxyphthalimide derivatives of pyrazolo[3,4-c]pyrazoles, Indian
• Journal of Chemistry, 47B (2008) 1892-1897.
• J.C. Vire, J.M. Kauffmann, Trends in electrochemistry in drug analysis, Current Topics in Electrochemistry, 3 (1994) 493-515.
• H. Shirinzadeh, A.D. Yilmaz, M. Gumustas, S. Suzen, S. Ozden, S.A. Ozkan, Electrochemical behavior of indole-3-carboxaldehyde izonicotinoyl hydrazones: Discussion on possible biological behavior, Combinatorial Chemistry and High Throughput Screening, 13 (2010) 619-627.
• K.R. Kumar, A. Raghavendra G.Prasad, V. Srilalitha, G. Narayana Swami, L.K. Ravindranath, Electrochemical studies of certain 1-(Toluenyl sulfonyl)-3-amino-4- (4’-substituted aryl hydrazono)-2-pyrazolin-5-ones, Revista Colombiana De Quimica, 40 (2011) 165-184.
• A.R.G. Prasad, V. Seshagiri, L.K. Ravindranath, Polarographic Investigations of Certain Propiophenone benzoic acid hydrazones, Jordan
• Journal of Chemistry, 6 (2011) 51-64.
• M.D. Reddy, A.R.G. Prasad, Y.N. Spoorthy, L.K. Ravindranath, Synthesis, antibacterial, and antifungal evaluation of novel mannich bases containing oxadiazole and pyrazole moieties, Journal of Applied Pharmacy, 4 (2013) 781-793.
• E.H. Rodd, Chemistry of Carbon Compounds, Vol. IV, Elsevier, Amsterdam, 1957, 273.
• Y.P. Kiteav, I.M. Skrebkova, L.I. Malosva, Study of the structure and reactivity of nitrogen-containing derivatives of carbonyl compounds, Izv. Akad. Nauk SSSR, Ser. Kim. Nauk., 10 (1970) 2068-2072.
• P. Zuman, C.L. Perrin, Organic Polarography, Wiley & Sons Limited, 1969, 229.
• P. Zuman, The Elucidation of Organic Electrode process, Academic Press, New York,n1969, 25.
• B. Nygaard, Azobenzene-hydrazobenzene polarographic reversibility problem, Arkiv. Kemi., 20 (1962) 163-183.
• L. Meites, Polarographic Techniques, Interscience, New York, 1967, 363.
• L.K. Ravindranath, S.R. Ramadas, S. Brahmaji Rao, Polarographic behaviour of arylazo pyrazoles, Electrochemica Acta, 28 (1983) 601-603.
• L. Meites,Y. Israel, The calculation of electrochemical kinetic parameters from polarographic current- potential curves, J. Am. Chem. Soc., 83 (1961) 4903- 4096.
• M.H. Elnagdi, H.M. Fahmy, M.A. Morsi, Polarographic activity of the arylhydrazones of α-cyanoketones as a criterion of their acidity, J. Electroanal. Chem., 68 (1976) 237-242.
• N.R. Bannerjee, Amina Siddiqui, H.R Sharma, Polarographic Studies on 3,5-Dimethyl-4-(4’- sulphonamido-benzenazo)-pyrazol, Indian J. Chem., 17A (1979) 513-516.
• J. Tomes, Polarographic studies on dropping mercury electrode. Verification of the equation of polarographic wavein the reversible electro deposion of cations, Collect. Czech. Chem. Commun., 9 (1937) 12-21.
• J. Koutecky, Theory of slow electrode reactions in the polarography and polarographic behaviour of a system in which the depolarizer is generated with a rapid chemical reaction from an electroinactive compound, . Coll. Czech. Chem. Commn., 18 (1953) 597-610.
• T. De Vries, J.L. Kroon, A millicoulometer method for the determination of polarographic n-values, J. Am. Chem. Soc., 75 (1953) 2484–2486.
• J.J. Lingane, Coulometric Analysis, J. Am. Chem. Soc., 67 (1945) 1916-1922.
• F. Feigl, Spot Test, Vol. 2, Elsevier, Amsterdam, 1954, 109.
• R.B. Carlin, R.G. Nelb, R.C. Odisos, The Benzidine Rearrangement. III. Kinetics of the Rearrangements of Hydrazobenzene, J. Am. Chem. Soc., 73 (1951) 1002-1007.
• K.B. Oldham, E.P. Parry, Use of polarography and pulse-polarography in the determination of the kinetic parameters of totally irreversible electroreductions, Anal. Chem., 40 (1968) 65–69 .
• T.M. Florence, Polarography of aromatic azo compounds. I. Effect of substituents on the electroreduction of azo compounds , Aust. J. Chem., 18 (1965) 609-619.
• S. Patai, The Chemistry of the hydrazo, azo and azoxy groups, Part I, John Wiley and Sons, Interscience, Publications, London, 1975, 479.
• P. Zuman , Topics in Organic Polarography, Plenum press, New York, 1970, 231.
• G. Holleck, L. Holleck, Depolarisatoradsorption als Ursache von Inhibitionswirkungen bei der Hydrazobenzoloxydation, Naturwissenschaften, 51 (1964) 212-222 .
• H.H. Jaffe, A reexaminationof the Hammett equation, Chem. Rev., 53 (1953) 191-261.
• K. Naik, A.R.G. Prasad, Y.N. Spoorthy, L.K. Ravindranath, Novel Mannich bases bearing pyrazolone moiety – Synthesis, characterization and electrochemical studies, Journal of Electrochemical Science and Engineering, 3 (2013) 57-79.
• A. Kumar, Environmental Biotechnology, Daya Publishing House, India, 2004, 154.
• R.S. Nicholson, I. Shain, Theory of Stationary Electrode Polarography - Single Scan and Cyclic Methods Applied to Reversible, Irreversible, and Kinetic Systems, Anal. Chem., 36 (1964) 706-723.
• G.J. Hills, B. Fleet, R.D. Jee, Electroanalytical Chemistry-Voltammetry, RSC Publishing, 1973, 179.
• P. Delahay, New Instrumental methods in electrochemistry, Interscience Publishers Inc., New York, 1966, 42.
• M. Pourobaix, Atlass of Electrochemical Equilibrie in aqueous solutions, Pergamon Press, New York, 1966, 330.
• F.I. Cheng, C.K. Martin, Ultramicrodisk electrode ensembles prepared by incorporating carbon paste into a microporous host membrane, Anal. Chem., 60 (1988) 2163-2165.