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Formation of a new CuII–triazole ester complex from 1,2-cyclohexanedione-bis(p-bromobenzohydrazone) compound as a consequence of copper(II)-catalyzed click reaction

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Abstract

Reaction of 1,2-cyclohexanedione-bis(p-bromobenzohydrazone) (CBB) as a bis-aroyl-hydrazone derivative with copper(II) nitrate trihydrate in acetonitrile under ambient conditions produced a mononuclear Cu(II) complex [Cu(TE)(NO3)2] (TE: triazole-ester) (1). TE is an intermediate which is formed in situ during the oxidation of CBB by Cu(II) ion based on so-called copper(II)-catalyzed click reaction. CBB and 1 are characterized with various techniques. On the basis of single-crystal X-ray crystallography, compound 1 is confirmed as a 4-coordinate mononuclear Cu(II) complex with a distorted square planner geometry. In this compound, copper is bound to the 1-N of two monodentate triazole ester molecules and two monodentate nitrate ions. Moreover, the antimicrobial activity of CBB and 1 against some selected pathogenic bacteria was investigated. Due to this study, these compounds showed a good antibacterial activity. In addition, the Hirshfeld surface analysis (dnorm surface and two-dimensional fingerprint plots) was performed to reveal the nature of intermolecular interactions in CBB and 1. The most important contributions for the crystal packing of CBB are mainly from H…H (28.8%), Br…H/H…Br (23.2%) and C…H/H…C (19.5%) interactions, while the most important contributions for the crystal packing of 1 are found to be from H…H (27%), O…H/H…O (23.7%) and Br…H/H…Br (19%) interactions.

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  • 01 May 2022

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References

  • Abarca B, Alkorta I, Ballesteros R, Blanco F, Chadlaoui M, Elguero J, Mojarrad F (2005) 3-(2-Pyridyl)-[1, 2, 3] triazolo [1, 5-a] pyridines. An experimental and theoretical (DFT) study of the ring–chain isomerization. Org Biomol Chem 3:3905–3910

    Article  CAS  PubMed  Google Scholar 

  • Abarca-González B (2002) The Chemistry of [1, 2, 3] Triazolo [1, 5-a] pyridines. J Enzyme Inhib Med Chem 17:359–367

    Article  PubMed  Google Scholar 

  • Addison C, Amos D, Sutton D, Hoyle W (1967) Infrared and Raman spectra of compounds containing bidentate nitrato-groups. J Chem Soc. 21:808–812

    Article  Google Scholar 

  • Adly OM, Emara AA (2014) Spectroscopic and biological studies of new binuclear metal complexes of a tridentate ONS hydrazone ligand derived from 4-amino-6-methyl-3-thioxo-3, 4-dihydro-1, 2, 4-triazin-5 (2H)-one and 4, 6-diacetylresorcinol. S Spectrochim Acta Part A: Mol Biomol Spectrosc 132:91–101

    Article  CAS  Google Scholar 

  • Ainscough EW, Brodie AM, Ranford JD, Waters JM (1991) Preparation and characterization of complexes of the antitumour copper (II) 2-formylpyridine thiosemicarbazone (HL) system and the single-crystal X-ray structures of [{Cu(HL)(CF3CO2)}2][CF3CO2]2 and [Cu(HL)(H2O)(CLO4)2]· 2H2O. J Chem Soc. 98:2125–2131

    Google Scholar 

  • Al-Karawi AJM (2017a) From mesogens to metallomesogens. Synthesis, characterisation, liquid crystal and luminescent properties. Liq Cryst 44:2285–2300

    Article  CAS  Google Scholar 

  • Al-Karawi AJM (2017b) Comprehensive comparison between the reaction of N, N’-cyclohexane-1, 2-diylidene-bis (4-methoxybenzoylhydrazide) with mercury (II) and copper (II) ions. Synthesis, structure and kinetics of complex formation. Russ J Coord Chem 43:113–126

    Article  CAS  Google Scholar 

  • Al-Karawi AJM, Kased AFH, Awad AA, OmarAli A-AB, Al-Qaisi ZHJ (2018) Designing of some photo-luminescent materials based on a new mesogenic asymmetrical azine series. J Mol Struct 1168:92–105

    Article  CAS  Google Scholar 

  • Al-Karawi AJM, Maatta E, Desper J, Maurmann L, Henderson RA, Buchholz A, Plass W (2016) Synthesis, structure, magnetic properties and kinetics of formation of a cluster containing a Cu3(μ3-OH) core supported by a triazole-based ligand. J Coord Chem 69:458–474

    Article  CAS  Google Scholar 

  • Al-Karawi AJM, OmarAli A-AB, Awad AA, Doungmo G, Terraschke H (2021a) Liquid crystal and photoluminescent properties of a series of symmetrical 1, 2-bis (4-alkoxybenzylidene) hydrazines bearing long-tails of hydrocarbon chain. Liq Cryst. 48:412–422

    Google Scholar 

  • Al-Karawi AJM, OmarAli A-AB, Mangelsen S, Dege N, Kansız S, Breuninger P, Baydere C, OmarAli OB (2021b) An unprecedented formation of new copper (II) complexes as bioactive materials based on copper-catalyzed click reaction. Polyhedron. 115084:11–19

    Google Scholar 

  • Avasthi K, Shukla L, Kant R, Ravikumar K (2014) Folded conformations due to arene interactions in dissymmetric and symmetric butylidene-linker models based on pyrazolo [3, 4-d] pyrimidine, purine and 7-deazapurine. Acta Cryst C70:555–561

    Google Scholar 

  • Awad AA, OmarAli A-AB, Al-Karawi AJM, Al-Qaisi ZHJ, Majeed SG (2019) Mesomorphism behaviour and photoluminescent properties of new asymmetrical 1, 2-di (4-alkoxybenzylidene) hydrazines. J Chem Res 43:67–77

    Article  CAS  Google Scholar 

  • Babahan I, Emirdağ-Öztürk S, Poyrazoğlu-Çoban E (2015) Spectroscopic and biological studies of new mononuclear metal complexes of a bidentate NN and NO hydrazone–oxime ligand derived from egonol. Spectrochim Acta Part A: Mol Biomol Spectrosc 141:300–306

    Article  CAS  Google Scholar 

  • Bacchi A, Bonardi A, Carcelli M, Mazza P, Pelagatti P, Pelizzi C, Pelizzi G, Solinas C, Zani F (1998) Organotin complexes with pyrrole-2, 5-dicarboxaldehyde bis (acylhydrazones). Synthesis, structure, antimicrobial activity and genotoxicity. J Inorg Biochem 69:101–112

    Article  CAS  PubMed  Google Scholar 

  • Badiger DS, Hunoor RS, Patil BR, Vadavi RS, Mangannavar CV, Muchchandi IS, Gudasi KB (2012) Synthesis, physico-chemical characterization and antimicrobial activities of 3-methoxysalicylaldehyde-2-aminobenzoylhydrazone and its transition metal complexes. J Mol Struct 1019:159–165

    Article  CAS  Google Scholar 

  • Bakale RP, Pathan AH, Naik GN, Machakanur SS, Mangannavar CV, Muchchandi IS, Gudasi KB (2014) Synthesis and characterization of transition metal complexes of hydrochloride salt of 3-chlorobenzaldehyde hydralazine hydrazone: a new class of possible anti-cariogenic agents. Appl Organomet Chem 28:720–724

    Article  CAS  Google Scholar 

  • Barros-García F, Luna-Giles F, Maldonado-Rogado M, Viñuelas-Zahínos E (2005) Ligation properties of 2-acetyl-2-thiazoline semicarbazone (ATsc): Isolation, spectroscopic and X-ray study of ATsc and its Cu (II) and Ni (II) complexes. Polyhedron 24:2972–2980

    Article  CAS  Google Scholar 

  • Bermejo MR, Pedrido R, González-Noya AM, Romero MJ, Vázquez M, Sorace L (2003) Conformational rearrangement of 2, 6-bis (1-salicyloylhydrazonoethyl) pyridine (H4daps) on complexation. Synthesis and X-ray characterisation of H4daps and its copper helicate complex [Cu (H2daps)(H2O)]2· 2CH3CN. New J Chem 27:1753–1759

    Article  CAS  Google Scholar 

  • Centore R, Carella A, Tuzi A, Capobianco A, Peluso A (2010) Competitive H-bonding synthons in organic hydrazides. Cryst Eng Comm 12:1186–1193

    Article  CAS  Google Scholar 

  • Chantrapromma S, Kwong HC, Prachumrat P, Kobkeatthawin T, Chia TS, Quah CK (2019) Crystal structure of (E)-N′-(3, 4-dihydroxybenzylidene)-4-hydroxybenzohydrazide. Acta Cryst E75:1280–1283

    Google Scholar 

  • Chuprakov S, Hwang FW, Gevorgyan V (2007) Rh-Catalyzed Transannulation of Pyridotriazoles with Alkynes and Nitriles. Angew Chem Int Ed 46:4757–4759

    Article  CAS  Google Scholar 

  • Cie S (2002) X-AREA Version 1.18 and X-RED32 Version 1.04. Darmstadt, Germany

  • Davies HM, Townsend RJ (2001) Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates. J Org Chem 66:6595–6603

    Article  CAS  PubMed  Google Scholar 

  • Demircioğlu Z, Kaştaş G, Kaştaş ÇA, Frank R (2019) Spectroscopic, XRD, Hirshfeld surface and DFT approach (chemical activity, ECT, NBO, FFA, NLO, MEP, NPA & MPA) of (E)-4-bromo-2-[(4-bromophenylimino)methyl]-6-ethoxyphenol. J Mol Struct 1191:129–137

    Article  CAS  Google Scholar 

  • Farrugia LJ (1997) ORTEP-3 for Windows-a version of ORTEP-III with a Graphical User Interface (GUI). J Appl Cryst 30:565–565

    Article  CAS  Google Scholar 

  • Farrugia LJ (1999) WinGX suite for small-molecule single-crystal crystallography. J Appl Cryst 32:837–838

    Article  CAS  Google Scholar 

  • Geary WJ (1971) The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord Chem Rev 7:81–122

    Article  CAS  Google Scholar 

  • Guru MM, Punniyamurthy T (2012) Copper (II)-Catalyzed Aerobic Oxidative Synthesis of Substituted 1, 2, 3-and 1, 2, 4-Triazoles from Bisarylhydrazones via C-H Functionalization/C–C/N–N/C–N Bonds Formation. J Org Chem 77:5063–5073

    Article  CAS  PubMed  Google Scholar 

  • Hadi A, Martin N, Seoane C, Soto JL, Albert A, Cano F (1992) Synthesis and crystal structure of piperidinium 2-aryl [1, 2, 4] triazolo [1, 5-a] pyridinides and their neutralization to 2-aryl [1, 2, 4] triazolo [1, 5-a] pyridines. J Heterocyclic Chem 29:1229–1235

    Article  CAS  Google Scholar 

  • Hammood AJ, Kased AFH, Al-Karawi AJM, Raseen SR, Tomi IHR, OmarAli A-AB (2017) Efficient and practical method for the synthesis of hydrophobic azines as liquid crystalline materials. Mol Cryst Liq Cryst 648:114–129

    Article  CAS  Google Scholar 

  • Harinath Y, Reddy DHK, Kumar BN, Apparao C, Seshaiah K (2013) Synthesis, spectral characterization and antioxidant activity studies of a bidentate Schiff base, 5-methyl thiophene-2-carboxaldehyde-carbohydrazone and its Cd(II), Cu(II), Ni(II) and Zn(II) complexes. Spectrochim Acta Part A: Mol Biomol Spectrosc 101:264–272

    Article  CAS  Google Scholar 

  • Hirayama T, Ueda S, Okada T, Tsurue N, Okuda K, Nagasawa H (2014) Facile One-Pot Synthesis of [1, 2, 3] Triazolo [1, 5-a] Pyridines from 2-Acylpyridines by Copper(II)-Catalyzed Oxidative N-N Bond Formation. Chem Eur J 20:4156–4162

    Article  CAS  PubMed  Google Scholar 

  • Hunoor RS, Patil BR, Badiger DS, Vm C, Muchchandi I, Gudasi KB (2015) Co (II), Ni (II), Cu (II) and Zn (II) complexes of isatinyl-2-aminobenzoylhydrazone: synthesis, characterization and anticancer activity. Appl Organomet Chem 29:101–108

    Article  CAS  Google Scholar 

  • Ilmi R, Kansız S, Al-Rasbi NK, Dege N, Raithby PR, Khan MS (2020) Towards white light emission from a hybrid thin film of a self-assembled ternary samarium(III) complex. New J Chem 44:5673–5683

    Article  CAS  Google Scholar 

  • Jones RN, Barry AL, Gavan TL, Washington JA, in: Lennette E H, Balows A, Hausler W J, Shadomy H J, (1985) Manual of Clinical Microbiology. American Society for Microbiology, Washington

    Google Scholar 

  • Kaplánek R, Havlík M, Dolenský B, Rak J, Džubák P, Konečný P, Hajdúch M, Králová J, Král V (2015) Synthesis and biological activity evaluation of hydrazone derivatives based on a Tröger’s base skeleton. Bioorg Med Chem 23:1651–1659

    Article  PubMed  CAS  Google Scholar 

  • Kaştaş G, Kaştaş ÇA (2019) Scrutinizing the two new o-hydroxy Schiff bases from the point of tautomeric behavior and non-covalent interactions (H-bond, Br…Br, π…π and C-H…π) in their supramolecular architectures. J Mol Struct 1184:427–434

    Article  CAS  Google Scholar 

  • Kharb R, Sharma PC, Yar MS (2011) Pharmacological significance of triazole scaffold. J Enzym Inhib Med Chem 26:1–21 (and references therein)

    Article  CAS  Google Scholar 

  • Kumar M, Roy S, Faizi MSH, Kumar S, Singh MK, Kishor S, Peter SC, John RP (2017) Synthesis, crystal structure and luminescence properties of acenaphthene benzohydrazide based ligand and its zinc (II) complex. J Mol Struct 1128:195–204

    Article  CAS  Google Scholar 

  • Lever ABP (1968) Inorganic electronic spectroscopy. Elsevier Publishing, New York

    Google Scholar 

  • Lever AP, Mantovani E, Ramaswamy B (1971) Infrared combination frequencies in coordination complexes containing nitrate groups in various coordination environments. A probe for the metal–nitrate interaction. Can J Chem 49:1957–1964

    Article  CAS  Google Scholar 

  • Liaw W-F, Horng Y-C, Ou D-S, Ching C-Y, Lee G-H, Peng S-M (1997) Distorted Square Planar Ni(II)−Chalcogenolate Carbonyl Complexes [Ni (CO)(SPh)n(SePh)3-n]-(n= 0, 1, 2): Relevance to the Nickel Site in CO Dehydrogenases and [NiFeSe] Hydrogenase. J Amer Chem Soc 119:9299–9300

    Article  CAS  Google Scholar 

  • Li Y, Yang Z-Y, Wang M-F (2010) Synthesis, characterization, DNA binding properties, fluorescence studies and antioxidant activity of transition metal complexes with hesperetin-2-hydroxy benzoyl hydrazone. J Fluoresc 20:891–905

    Article  PubMed  CAS  Google Scholar 

  • López-Torres E, Mendiola MA (2009) Structural diversity of benzil bis (benzoylhydrazone): Mononuclear, binuclear and trinuclear complexes. Dalton Trans. 56:7639–7647

    Article  CAS  Google Scholar 

  • Mckinnon JJ, Spackman MA, Mitchell AS (2004) Novel tools for visualizing and exploring intermolecular interactions in molecular crystals. Acta Cryst B 60:627–668

    Article  CAS  Google Scholar 

  • Mistri T, Dolai M, Chakraborty D, Khuda-Bukhsh AR, Das KK, Ali MA (2012) Highly selective and sensitive in vivo fluorosensor for zinc (II) without cytotoxicity. Org Biomol Chem 10:2380–2384

    Article  CAS  PubMed  Google Scholar 

  • OmarAli A-A, Al-Karawi AJM, Awad AA, Dege N, Kansız S, Agar E, Hussein ZA, Mohammed IR (2020a) Two new zinc (II) and mercury (II) complexes based on N, N′-(cyclohexane-1, 2-diylidene) bis (4-fluorobenzoylhydrazide): synthesis, crystal structures and antibacterial activities. Acta Cryst C76:476–482

    Google Scholar 

  • OmarAli A-A, Al-Karawi AJM, Dege N, Kansız S, Ithawi HAD (2020b) Synthesis and X-ray crystal structures of two different zinc (II) complexes of N, N′-cyclohexane-1, 2-diylidene-bis (4-fluorobenzoylhydrazide) based on zinc salt effect. J Mol Str. 128387:46–48

    Google Scholar 

  • Peng X, Tang X, Qin W, Dou W, Guo Y, Zheng J, Liu W, Wang D (2011) Aroylhydrazone derivative as fluorescent sensor for highly selective recognition of Zn2+ ions: syntheses, characterization, crystal structures and spectroscopic properties. Dalton Trans 40:5271–5277. Rodríguez-Argüelles M C, Cao R, García-Deibe A M, Pelizzi C, Sanmartín-Matalobos J, Zani F (2009) Antibacterial and antifungal activity of metal (II) complexes of acylhydrazones of 3-isatin and 3-(N-methyl) isatin. Polyhedron 28:2187–2195

    CAS  Google Scholar 

  • Popiołek Ł (2017) Hydrazide–hydrazones as potential antimicrobial agents: overview of the literature since 2010. Med Chem Res 26:287–301

    Article  PubMed  CAS  Google Scholar 

  • Rodríguez-Argüelles MC, Cao R, García-Deibe AM, Pelizzi C, Sanmartín-Matalobos J, Zani F (2009) Antibacterial and antifungal activity of metal (II) complexes of acylhydrazones of 3-isatin and 3-(N-methyl) isatin. Polyhedron 28:2187–2195

    Article  CAS  Google Scholar 

  • Rodríguez-Hermida S, Lago AB, Carballo R, Fabelo O, Vázquez-López EM (2015) Homo and Heteronuclear Compounds with a Symmetrical Bis-hydrazone Ligand: Synthesis, Structural Studies and Luminescent Properties. Chem Eur J 21:6605–6616

    Article  PubMed  CAS  Google Scholar 

  • Shaban M, Nassr M, El Ashry E, Mustafa M (1977) Reactions of Aroylhydrazones. III: Oxidative cyclization of cyclohexane-1, 2-dione bis (aroylhydrazones) to substituted 1, 2, 3-triazoles. Org Prep Proc Int 9:117–124

    Article  CAS  Google Scholar 

  • Sheldrick GM (1997a) Program for the solution of crystal structures, SHELXL-97. University of Göttingen, Germany

    Google Scholar 

  • Sheldrick GM (1997b) Program for Crystal Structures Refinement, SHELXL-97. University of Göttingen, Germany

    Google Scholar 

  • Silverstein R, Webster F, Kiemle D, Bryce D (2014) Spectrophotometric Identification of Organic Compounds. Wiley, New York

    Google Scholar 

  • Singh R P, Gao H, Meshri D T, Jean'ne M S (2007) Nitrogen-rich heterocycles, in: High energy density materials.Springer, New York

  • Singh VP, Singh S, Katiyar A (2009) Synthesis, physico-chemical studies of manganese (II), cobalt (II), nickel (II), copper (II) and zinc (II) complexes with some p-substituted acetophenone benzoylhydrazones and their antimicrobial activity. J Enzym Inhib Med Chem 24:577–588

    Article  CAS  Google Scholar 

  • Singh VP, Singh S, Singh DP (2012) Synthesis, characterization and biocidal activity of some transition metal (II) complexes with isatin salicylaldehyde acyldihydrazones. J Enzym Inhib Med Chem 27:319–329

    Article  CAS  Google Scholar 

  • Souza P, Matesanz AI, Fernández V (1996) Copper(II) and cobalt(II) complexes of methyl 2-pyridyl ketone thiosemicarbazone (HL); single-crystal structure of [Cu(HL)L]NCS. J Chem Soc, Dalton Trans. 90:3011–3013

    Article  Google Scholar 

  • Spackman MA, Jayatilaka D (2009) Hirshfeld surface analysis. Cryst Eng Comm 11:19–32

    Article  CAS  Google Scholar 

  • Spek AL (2009) Structure validation in chemical crystallography. Acta Cryst D65:148–155

    Google Scholar 

  • Stadler A-M, Harrowfield J (2009) Bis-acyl-/aroyl-hydrazones as multidentate ligands. Inorg Chim Acta 362:4298–4314

    Article  CAS  Google Scholar 

  • Sundar A, Prabhu M, Gandhi NI, Marappan M, Rajagopal G (2014) Synthesis, characterization, structural analysis of metal (II) complexes of N′-[(E)-3-Bromo-5-Chloro-2-hydroxybenzidene]-4-hydroxybenzohydrazide—Multisubstituted Schiff base as a F− and Cu2+ ions selective chemosensor. Spectrochim Acta Part A: Mol Biomol Spectrosc 129:509–518

    Article  CAS  Google Scholar 

  • Turner M J, MacKinnon J J, Wolff S K, Grimwood D J, Spackman P R, Jayatilaka D, Spackman M A (2017). Crystal Explorer Ver. 17.5. University of Western Australia, Pert.

  • Verma G, Marella A, Shaquiquzzaman M, Akhtar M, Ali MR, Alam MM (2014) A review exploring biological activities of hydrazones. J Pharm Bioallied Sci 6:69–80

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Viñuelas-Zahínos E, Maldonado-Rogado M, Luna-Giles F, Barros-García F (2008) Coordination behaviour of Schiff base 2-acetyl-2-thiazoline hydrazone (ATH) towards cobalt (II), nickel (II) and copper (II). Polyhedron 27:879–886

    Article  CAS  Google Scholar 

  • Zhang Z-Y, Sun X-W (1998) s-triazolo [3, 4-b]-1, 3, 4-thiadiazole derivatives. Heterocycles 3:561–584

    Article  Google Scholar 

  • Todea AM, Al-Karawi AJM, Glaser T, Walleck S, Chamoreau L-M,Thouvenot R, Gouzerh P, Müller A (2012) Encapsulation of Keggin-type anions in reduced molybdenum–iron-type Keplerates as a general phenomenon. Inorg Chim Acta 389:107–111

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Acknowledgments

We are so grateful to Mustansiriyah University/ Baghdad, Iraq (https://uomustansiriyah.edu.iq) and Ondokuz Mayıs University/ Samsun, Turkey for support and access to facilities. N. Dege would like to thank Ondokuz Mayıs University/ Samsun, Turkey for the financial support.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Mustansiriyah University, P.O. Box 46010, Baghdad, Iraq

    Ahmed Jasim M. Al-Karawi & Al-Ameen Bariz OmarAli

  2. Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139, Samsun, Turkey

    Necmi Dege

  3. Department of Fundamental Sciences, Faculty of Engineering, Samsun University, Samsun, 55420, Turkey

    Sevgi Kansız

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  1. Ahmed Jasim M. Al-Karawi
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Al-Karawi, A.J.M., OmarAli, AA.B., Dege, N. et al. Formation of a new CuII–triazole ester complex from 1,2-cyclohexanedione-bis(p-bromobenzohydrazone) compound as a consequence of copper(II)-catalyzed click reaction. Chem. Pap. 75, 3901–3914 (2021). https://doi.org/10.1007/s11696-021-01614-x

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