Synthesis, Spectral Analysis and Antimicrobial Activity of New Pd (II) Complexes Involving 5,6-Dimethylbenzimidazole

Abstract

In this study, firstly, 3-bromopropanenitrile(2a), ethyl bromoacetate(2b), and 2-bromoethan-1-amine(2c) were added to 5,6-dimethylbenzimidazole(1) and symmetrically-connected N-heterocyclic carbenes(NHC)[(3a–3c)] were synthesized. Then, the NHC precursor compounds were reacted with PdCl₂ and Pd (II)-NHC complexes[(4a—4c)] were obtained. The synthesized NHC precursors(3a–3c) and Pd( II)-NHC complexes(4a—4c) were characterized by different spectroscopic methods. The antibacterial activities of these products were measured against bacteria and fungus with the disc diffusion method. Pd(II)-NHC complexes had higher antibacterial activity than the NHC precursors. The synthesized compounds showed antimicrobial activity with different properties from each other. In vitro biological activities of salts and metal complexes on selected bacteria were determined by the broth dilution method based on Clinical and Laboratory Standards Institute guidelines. 1,3-Bis-(2-hydroxyethyl) imidazolinium bromide and 3-(2-ethoxy-2-oxoethyl)-1-(3-aminopropyl)-1H-imidazole-3-ium bromide had activity against Escherichia coli.

Keywords

N-Heterocyclic carbene / Palladium(II)-NHC complex / Structural analysis / Antimicrobial activity

References

[1] Glorius F. N-Heterocyclic Carbenes in Transition Metal Catalysis, 2006, Berlin: Springer-Verlag

[2] Wurtz S, Glorius F. Acc. Chem. Res., 2008, 41: 1523.

[3] Hashmi A S K, Lothschuetz C, Graf K, Haeffner T, Schuster A, Rominger F. Adv. Synth. and Catal., 2011, 353(9): 1407.

[4] Oehninger L, Rubbiani R, Ott I. Dalton Trans., 2013, 42(16): 3269.

[5] Cisnetti F, Gibard C, Gautier A. J. Organomet. Chem., 2015, 782: 22.

[6] Fortman G C, Nolan S P. Chem. Soc. Rev., 2011, 40(10): 5151.

[7] Nemcsok D, Wichmann K, Frenking G. Organometallics, 2004, 23(15): 3640.

[8] Gaillard S, Nun P, Slawin A M Z, Nolan S P. Organometallics, 2010, 29(21): 5402.

[9] Li W S, Wang C H, Ko S, Chang T T, Jen Y C, Yao C F, More S V, Jao S C. Journal of Medicinal Chemistry, 2012, 55(4): 1583.

[10] Peris E, Crabtree R H. Coordination Chemistry Reviews, 2004, 248(21–24): 2239.

[11] Ray S, Mohan R, Singh J K, Samantaray M K, Shaikh M M, Panda D, Ghosh P. J. Am. Chem. Soc., 2007, 129(48): 15042.

[12] Kleinman EF. The Bimolecular Aliphatic Mannich and Related Reactions in Comprehensive Organic Synthesis, 1991, Oxford: Pergamon Press

[13] Fekri A, Keshk E M, Khalil A G M, Taha I. Mol. Divers, 2022, 26: 781.

[14] Scattolin T, Bortolamiol E, Palazzolo S, Caligiuri I, Perin T, Canzonieri V, Demitri N, Rizzolio F, Cavallo L, Dereli B, Mane M V, Nolan S P, Visentin F. Chem. Commun., 2020, 56: 12238.

[15] Liu J, Zhou X, Rao H, Xiao F, Li C J. Chemistry: A European Journal, 2011, 17(29): 7996.

[16] Ofele K. Journal of Organometallic Chemistry, 1968, 12: 42.

[17] Wanzlick H W, Schönherr H J. Angewandte Chemie International Edition, 1968, 7(2): 141.

[18] Peris E. Chemical Reviews, 2018, 118(19): 9988.

[19] Yang J. J. Coord. Chem., 2017, 70: 441.

[20] Liang R X, Jia Y X. Acc. Chem. Res., 2022, 55(5): 734.

[21] Ehrentraut A, Zapf A, Beller M. Synlett., 2000, 11: 1589.

[22] Xiao J, Wang L, Zhang H, Ma N, Tao M, Zhang W. Chemical Engineering Science, 2022, 247(16): 117053.

[23] Samiee S, Shiralinia A, Hoveizi E, Gable R W. Inorganica Chimica Acta, 2022, 538: 120964.

[24] Gu S, Chen C, Qiu H, Chen W. Current Organic Chemistry, 2011, 15: 3291.

[25] Guisado-Barrios G, Hiller J, Peris E. Chem. Eur. J., 2013, 19: 10405.

[26] Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev., 2014, 114: 9047.

[27] Burrows A D. Sci. Prog., 2002, 85: 199.

[28] Crabtree R H. New J. Chem., 2011, 35: 18.

[29] Dahm G, Borre E, Guichard G, Bellemin-Laponnaz S. Eur. J. Inorg. Chem., 2015, 2015(10): 1665.

[30] Simic D, Zaric M, Nikolic I, Zivkovic-Zaric R, Canovic P, Kocovic A, Radojevic I, Rakovic I, Jovicic S, Petrovic D, Stojkovic D, Vukovic N, Kacaniova M, Vukic M, Jevtic V. Dalton Transactions, 2022, 51: 1191.

[31] Clinical and Laboratory Standards Institute Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, Approved standard—Second Edition, 2002, Wayne, Pennsylvania: NCCLS Document M27-A2(ISBN 1-56238-469-4)

[32] Clinical and Laboratory Standards Institute Performance Standards for Antimicrobial Susceptibility Testing, Twenty-second Informational Supplement, 2012, Wayne, Pennsylvania: CLSI Document M100-S22

[33] Kaya E, Ozbilge H. Turk. J. Med. Sci., 2012, 42(2): 325.

[34] Altun Ö, Koçer M Ö. J. Mol. Struc., 2021, 1224(129242): 1.

[35] Cajiao N, Mora H, Palencia M. Journal of Science with Technological Applications, 201, 1(1): 77.

[36] Cai W, Wang J, Chu C, Chen W, Wu C, Liu G. Advenced Science, 2018, 6(1): 1801526.

[37] Ma S, Zhou Z, Ran G, Xie J, Luo X, Li Y, Wang L. Journal of Hazardous Materials, 2022, 422: 126785.

[38] Geary W J. Coord. Chem. Rev., 1971, 7(1): 81.

[39] Kettle S F A. Coordination Compounds, 1975, London: Thomas Nelson and Sons

[40] Dyer J R. Application of Absorption Spectroscopy of Organic Compounds, 1965, New Jersey: Prentice-Hall

[41] Lever A B P. Inorganic Electronic Spectroscopy, 1984, New York: Elsevier

[42] Kang J G, Cho D H, Park C, Kang S K, Kim I T, Lee S W, Lee H H, Lee Y N, Lim D W, Lee S J, Kim S H, Bae Y J. Bull. Korean Chem. Soc., 2008, 29(3): 599.

[43] Jambi S M S, Kandil S S. J. Mater. Environ. Sci., 2012, 3(3): 591.

[44] Lambert J B, Shurwell H F, Verbit L, Cooks R G, Stout G H. Organic Structural Analysis, 1976, New York: MacMillan

[45] Nakamato K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 1997, New York: John Wiley and Sons

[46] Socrates G. Infrared Characterization Group Frequencies: Tables and Charts, 3rd Edition, 2004, London: John Wiley and Sons

[47] Giovagnini L, Ronconi L, Aldinucci D, Lorenzon D, Sitran S, Fregona D. J. Med. Chem., 2005, 48(5): 1588.

[48] Salem M A, Bakr E A, El-Attar H G. Spectrochim. Acta, Part A, 2018, 188: 155.

[49] Warren B E. X-Ray Diffraction, 1990, New York: Dover

[50] Barbosa H F G, Attjioui M, Ferreira A P G, Dockal E R, El Gueddari N E, Moerschbacher B M, Cavalheiro E T G. Molecules, 2017, 22(1987): 1.

[51] Kavitha K, Reddy L. Arab. J. Chem., 201, 9(5): 640.

[52] Yılmaz V T, Ertem A, Guney E, Buyukgungor O. Z. Anorg. Allg. Chem., 2010, 636(3/4): 610.

[53] Maskovic J M, Maskovic P Z, Koval’chuk T V, Loginova N V, Trifunovic S R. Der Chemica Sinica, 2018, 9(1): 535.

[54] Al-Hamdani A A S, Balkhı A M, Falah A, Shaker S A. J. Chil. Chem. Soc., 2015, 60(1): 2774.

[55] Pahontu E, Paraschivescu C, Ilies D C, Poirier D, Oprean C, Paunescu V, Gulea A, Rosu T, Bratu O. Molecules, 201, 21(5): 1.

[56] Kumar V A, Sarala Y, Siddikha A, Vanitha S, Babu S, Reddy A V. J. Appl. Pharm. Sci., 2018, 8(4): 071.

[57] Mihalache M, Negreanu-Pirjol T, Dumitraşu F, Draghici C, Calinescu M. J. Serb. Chem. Soc., 2018, 83(3): 271.