DETERMINATION AND EVALUATION OF ACIDITY CONSTANTS OF SOME IMIDAZOLE AND THIAZOLE LINKED ACETAMIDE COMPOUNDS

Year 2016, Volume: 17 Issue: 2, 263 - 272, 14.07.2016

Funda Tay , Murat Duran , Cihan İspir Şeref Demirayak

https://doi.org/10.18038/btda.96904

Abstract

In this work, the effect of substituents on the acidity constants of some acetamide derivatives was investigated. The acidity constants of nine acetamide derivatives were determined at 25 °C using a UV spectrophotometric method. When the molecules possessed different substituents the values of the acidity constants changed from 6.01 to 8.22 for the first protonation and from 3.07 to 4.73 for the second protonation. The first protonation under these circumstances was observed to occur on the nitrogen atom of the 2-mercaptoimidazole ring. The second protonation was observed to occur on the nitrogen atom of the thiazole ring.

Keywords

İmidazol, Tiyazol; Asetamit; Protonlanma yolları; UV spektroskopi; pKa

DETERMINATION AND EVALUATION OF ACIDITY CONSTANTS OF SOME IMIDAZOLE AND THIAZOLE LINKED ACETAMIDE COMPOUNDS

Abstract

References

• Foulon C, Duhal N, Lacroix-Callens B, Vaccher C, Bonte JP, Goossens JF. Determination of pK(a) values of benzoxa-, benzothia- and benzoselena-zolinone derivatives by capillary electrophoresis - Comparison with potentiometric titration and spectrometric data. Eur J Pharm Sci 2007; 31: 165-171.
• Corona-Avendano S, Alarcon-Angeles G, Rojas-Hernandez A, Romero-Romo MA, Ramirez-Silva MT. Study on the stability of adrenaline and on the determination of its acidity constants. Spectrochim Acta A 2005; 61: 305-311.
• Alizadeh K, Ghiasvand AR, Borzoei M, Zohrevand S, Rezaei B, Hashemi P, Shamsipur M, Maddah B, Morsali A, Akhbari K, Yavari I. Experimental and computational study on the aqueous acidity constants of some new aminobenzoic acid compounds. J Mol Liq 2009; 149: 60-65.
• Alizdeh K, Rezaei B, Maddah B. Spectrophotometric determination of aqueous acidity constants of three azo dyes. Cent Eur J Chem 2010; 8: 392-395.
• Niazi A, Yazdanipour A, Ghasemi J, Amini A, Bozorgzad S, Kubista M. Spectrophotometric investigation of the acidity constants of fluorescein in various water-organic solvent media. Chem Eng Commun 2008; 195: 1257-1268.
• Bordbar M, Faal AY, Ahari-Mostafavi MM, Gharagozlou M, Fazaeli R. Multi-wavelength spectrophotometric determination of acidity constants of some salicylaldimine derivatives. J Mol Liq 2013; 178: 70-77.
• Huang Y, Liu LH, Liu WH, Liu SG, Liu SB. Modeling Molecular Acidity with Electronic Properties and Hammett Constants for Substituted Benzoic Acids. J. Phys. Chem. A2011; 115: 14697-14707.
• Diaz D, Ford KA, Hartley DP, Harstad EB, Cain GR, Achilles-Poon K, Nguyen T, Peng J, Zheng Z, Merchant M, Sutherlin DP, Gaudino JJ, Kaus R, Lewin-Koh SC, Choo EF, Liederer BM, Dambach DM.. Pharmacokinetic drivers of toxicity for basic molecules: Strategy to lower pKa results in decreased tissue exposure and toxicity for a small molecule Met inhibitor. Toxicol Appl Pharm 2013; 266: 86-94.
• Duran, M, Canbaz MC. pKa Determination of Newly Synthesized N-(benzothiazole-2-yl)-2-(4,5- dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio) acetamide derivatives. Ind Eng Chem Res 2013; 52: 8355-8360.
• Öğretir C, Demirayak S, Tay NF, Duran M. Determination and evaluation of Acid Dissociation Constants of Some Substituted 2-Aminobenzothiazole Derivatives. J Chem Eng Data 2008; 53: 422- 426.
• Tay F, Arslan TA. Theoretical Study on Basicity Behaviour of Some 4- Amino Quinazoline Derivatives. AUJST-B 2011; 1(2): 141-148.
• Tay F, Duran M, Demirayak S. A Quantum chemical DFT/HF study on acidity constants of some benzothiazole and thiazole derivatives. Indian J Chem B 2014; 53: 102-110.
• Jorgensen WL, Briggs JM, Gao J. A Priori Calculations of Pkas for Organic-Compounds in Water - the pKa of Ethane. J Am Chem Soc 1987; 109: 6857-6858.
• Potter MJ, Gilson MK, Mccammon JA.. Molecule pK(a) Prediction with Continuum Electrostatics Calculations. J Am Chem Soc 1994; 116: 10298-10299.
• Fotouhi L, Asadi S, Tammari E, Heravi MM, Nematollahi D. Electrochemical Oxidation of Catechol and 4-tert-Butylcatechol in the Presence of 1-Methyl-1H-imidazole-2-thiol: Synthesis and Kinetic Study. J Iran Chem Soc2008; 5: 712-717.
• Kara D, Alkan M. Determination of acidity constants of acid-base indicators by second-derivative spectrophotometry. Spectrochim Acta A 2000; 56: 2753-2761.
• Blasko A, Bunton CA, Bunel S, Ibarra C, Moraga E. Determination of acid dissociation constants of anomers of amino sugars by H-1 NMR spectroscopy. Carbohyd Res 1997; 298: 163-172.
• Lachenwitzer A, Li N, Lipkowski J. Determination of the acid dissociation constant for bisulfate adsorbed at the Pt(111) electrode by subtractively normalized interfacial Fourier transform infrared spectroscopy. Journal of Electroanal Chem 2002; 532: 85-98.
• Rouhani S, Rezaei R, Sharghi H, Shamsipur M, Rounaghi G. Spectrophotometric Determination of Acidity Constants of Some Anthraquinone Derivatives in Binary Methanol-Water Mixtures. Microchem J 1995;52: 22-27.
• Elbagerma MA, Edwards HGM, Azimi GIJ. Raman spectroscopic determination of the acidity constants of salicylaldoxime Scowen in aqueous solution. J Raman Spectrosc 2011; 42: 505-511.
• Eseola AO, Obi-Egbedi NO. Spectroscopic study of 2-, 4-and 5-substituents on pK(a) values of imidazole heterocycles prone to intramolecular proton-electrons transfer. Spectrochim Acta A 2010; 75: 693-701.
• Gladysheva T, Liu JY, Rosen BP. His-8 lowers the pK(a) of the essential Cys-12 residue of the ArsC arsenate reductase of plasmid R773. J Biol Chem 1996; 271: 33256-33260.
• Ulusoy N, Kiraz M, Kucukbasmaci O. New 6-(4-bromophenyl)imidazo[2,1-b]thiazole derivatives: Synthesis and antimicrobial activity. Monatsh Chem 2002; 133: 1305-1315.
• Kaplancikli ZA, Turan-Zitouni G, Revial G, Guven K.. Synthesis and study of antibacterial and antifungal activities of novel 2-[[(benzoxazole/benzimidazole-2-yl)sulfanyl] acetylamino]thiazoles. Arch Pharm Res2004; 27: 1081-1085.
• Desai NC, Joshi VV, Rajpara KM, Vaghani HV, Satodiya HM.. Facile synthesis of novel fluorine containing pyrazole based thiazole derivatives and evaluation of antimicrobial activity. J Fluorine Chem2012; 142: 67-78.
• Karpov KA, Nazarenko AV, Pekarevskii BV, Potekhin VM. Biocidal and anticorrosive effect of 2-aminothiazole derivatives used as additives to jet fuels. Russ J Appl Chem+2001; 74: 998-1001.
• Rehse K, Baselt T. New 2-Amino-thiazole-4-acetamides with Antiplatelet Activity, Archiv der Pharmazie 2008;341:645-654.
• Karade HN, Acharya BN, Sathe M, Kaushik MP. Design, synthesis, and antimalarial evaluation of thiazole-derived amino acids. Med Chem Res 2008; 17: 19-29.
• Moldovan CM, Oniga O, Parvu A, Tiperciuc B, Verite P, Pirnau A, Crisan O, Bojita M, Pop R.. Synthesis and anti-inflammatory evaluation of some new acyl-hydrazones bearing 2-aryl-thiazole.Eur J Med Chem. 2011; 46: 526-534.
• Mungra DC, Kathrotiya HG, Ladani NK, Patel MP, Patel RG. Molecular iodine catalyzed synthesis of tetrazolo[1,5-a]-quinoline based imidazoles as a new class of antimicrobial and antituberculosis agents.Chinese Chem Lett 2012;23: 1367-1370.
• Duran M, Demirayak S. Synthesis of 2-[4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio]-N- (thiazole-2-yl)acetamide derivatives and their anticancer activities. Med Chem Res 2013; 22: 4110- 4124.
• Samus NM, Mel'nik SV, Tsapkov VI. Coordination compounds of cobalt, nickel, and copper with some 4-(salicylideneamino)benzenesulfonamides.Russ J of Gen Chem 2000; 70: 281-286.
• Svanvik N, Westman G, Wang DY, Kubista M. Light-up probes: Thiazole orange-conjugated peptide nucleic acid for detection of target nucleic acid in homogeneous solution. Anal Biochem2000; 281: 26-35.
• Samus NM, Alnabgaly N, Shlyakhov EN, Tsapkov VI, Burdenko TA, Stan VV. Synthesis and Antimicrobial Activity of Coordination-Compounds of 3d Elements with Schiffs Bases Derived from 5-Nitrofurfurol and Some Sulfanilamides. KhimFarm ZH+ 1991; 25:37-39.
• Solmaz R, Kardas G. Electrochemical synthesis and characterization of poly-2-aminothiazole, Prog Org Coat 2009; 64: 81-88.
• Atta NF. Electrochemical synthesis, characterization and some properties of a polymer derived from thioflavin S. Eur Polym J 2005;41: 3018-3025.
• Jenkins IH, Pickup PG. Electronically Conducting Polymers Containing Conjugated Bithiazole Moieties from Bis(Thienyl)Bithiazoles. Macromolecules 1993; 26: 4450-4456.
• Zhao H, Jiang Y, Ma YR, Wu ZJ, Cao Q, He YJ, Li XJ, Yuan ZB. Poly(2-amino-4-thiazoleacetic acid)/multiwalled carbon nanotubes modified glassy carbon electrodes for the electrochemical detection of copper(II). Electrochim Acta2010; 55: 2518-2521.
• Kalimuthu P, John SA. Simultaneous determination of ascorbic acid, dopamine, uric acid and xanthine using a nanostructured polymer film modified electrode. Talanta 2010; 80: 1686-1691.
• Kalimuthu P, John SA.. Electropolymerized film of functionalized thiadiazole on glassy carbon electrode for the simultaneous determination of ascorbic acid, dopamine and uric acid. Bioelectrochemistry 2009; 77: 13-18.
• Kalimuthu P, John SA,. Simultaneous determination of epinephrine, uric acid and xanthine in the presence of ascorbic acid using an ultrathin polymer film of 5-amino-1,3,4-thiadiazole-2-thiol modified electrode. Anal Chim Acta2009; 647: 97-103.
• Au-Alvarez O, Peterson RC, Crespo AA, Esteva YR, Alvarez HM, Stiven AMP, Hernandez RP.. 2-amino-4-phenylthiazole. Acta Crystallogr C 1999; 55: 821-823.
• Robinson RA, Stokes RH. Electrolyte Solutions, The Measurement and Interpretation of Conductance, Chemical Potential, and Diffusion in Solutions of Simple Electrolytes. London: Butterworths, 1968. pp 545-548.
• Bowden K. Acidity functions for strongly basic solutions. Chem Rev 1966; 66: 2.
• Cookson RF. The determination of acidity constants. Chem Rev 1974; 74: 1.
• Albert, A, Serjeant EP. The determination of Ionisation Constants, London: Chapman and Hall, 1984.
• Gupta RR, Kumar M, Gupta V. Heterocyclic Chemistry. Five Membered Heterocycles, Vol.II, Germany: Springer, 1999. pp 385-386.
• Strauss U, Haerter H P, Schindler O. Vergleich der Dissoziationskonstanten von 2-Amino- thiazol- und 2-Amino-oxazol-Derivaten. Chimia 1973; 27: 99–102.