Synthesis and Structural Investigations of 1, 2-bis(2-ethoxybenzylidene)hydrazine

Year 2023, Volume: 27 Issue: 4, 768 - 780, 25.08.2023

Sevgi Kansız

https://doi.org/10.16984/saufenbilder.1227659

Abstract

The titled compound, 1,2-bis(2-ethoxybenzylidene) hydrazine was developed using the reaction of 2-ethoxybenzaldehyde and hydrazine monohydrate in an ethanolic solution. In the Schiff-based hydrazine compound, C18H20N2O2, the mid-point of the nitrogen atoms of the central hydrazine moiety is located in inversion symmetry. In C18H20N2O2, C−H···N hydrogen bond linked the molecules, and the framework stabilized by weak C−H···π and π···π stacking interactions. MEP, HOMO and LUMO analysis were performed with the DFT/B3LYP method and the 6-311+G(d,p) basis set. The energies of frontier orbitals were calculated to understand specific molecular properties such as electronegativity, chemical reactivity, chemical hardness and softness. For investigating the contributions of various intermolecular contacts within the hydrazine compound, Hirshfeld surface analysis was performed. The largest contribution of the compound to the main interactions comes from the H···H (64%), C···H (16%) and N···H (9%) interactions.

Keywords

: Schiff base, hydrazine, X-ray, DFT, Hirshfeld surface analysis

References

• P. Noblia, M. Vieites, B. S. Parajon-Costa, E. J. Baran, H. Cerecetto, P. Draper, M. Gonzalez, O. E. Piro, E. E. Castellano, A. Azqueta, A. L. de Cerain A. Monge-Vega, D. Gambino, “Vanadium(V) complexes with salicylaldehyde semicarbazone derivatives bearing in vitro anti-tumor activity toward kidney tumor cells (TK-10): crystal structure of [(VO2)-O-V(5-bromosalicylaldehyde semicarbazone)],” Journal of Inorganic Biochemistry, vol. 99, no. 2, pp. 443–451, 2005.
• R. K. Mohapatra, A. K. Sarangi, M. Azam, M. M. El-ajaily, M. Kudrat-E-Zahan, S. B. Patjoshi, D. C. Dash, “Synthesis, structural investigations, DFT, molecular docking and antifungal studies of transition metal complexes with benzothiazole based Schiff base ligands,” Journal of Molecular Structure, vol. 1179, pp. 65–75, 2019.
• T. Vijayan, J. Kim, M. Azam, S. L. Al-Resayes, A. Stalin, B. S. Kannan, M. Jayamani, A. Ayyakannu, S. Nallathambi, “Influence of co-ligand on the biological properties of Schiff base metal complexes: Synthesis, characterization, cytotoxicity, and antimicrobial studies,” Applied Organometallic Chemistry, vol. e6542, 2021.
• N. Poulter, M. Donaldson, G. Mulley, L. Duque, N. Waterfield, A.G. Shard, S. Spencer, A. T. A. Jenkins, A. L. Johnson, “Plasma deposited metal Schiff-base compounds as antimicrobials,” New Journal of Chemistry, vol. 35, no. 7, pp. 1477–1484, 2011.
• M. Azam, S. M. Wabaidur, M. J. Alam, A. Trzesowska-Kruszynska, R. Kruszynski, M. Alam, S. I. Al-Resayes, S. Dwivedi, M. R. Khan, M. S. Islam, N. T. M. Ibaqami, “Synthesis, structural investigations and pharmacological properties of a new zinc complex with a N4-donor Schiff base incorporating 2-pyridyl ring,” Inorganica Chimica Acta, vol. 487, pp. 97–106, 2019.
• P. G. Cozzi, “Metal-Salen Schiff base complexes in catalysis: practical aspects,” Chemical Society Reviews, vol. 33, no. 7, pp. 410–421, 2004.
• P. R. Reddy, A. Shilpa, N. Raju, P. Raghavaiah, “Synthesis, structure, DNA binding and cleavage properties of ternary amino acid Schiff base-phen/bipy Cu(II) complexes,” Journal of Inorganic Biochemistry, vol. 105, no. 12, pp. 1603–1612, 2011.
• D. W. Roberts, T. W. Schultz, A. M. Api, “Skin Sensitization QMM for HRIPT NOEL data: Aldehyde Schiff-Base domain,” Chemical Research in Toxicology, vol. 30, no. 6, pp. 1309–1316, 2017.
• K. M. Abuamer, A. A. Maihub, M. M. El-Ajaily, A. M. Etorki, M. M. Abou-Krisha, “The role of aromatic Schiff bases in the dyes techniques,” International Journal of Organic Chemistry, vol. 04, no. 01, pp. 7–15, 2014.
• V. G. Vlasenko, A. S. Burlov, T. A. Kuz'menko, A. T. Kozakov, A. V. Nikol'skii, A. L. Trigub, S. I. Levchenkov, “Synthesis, structure, and X-ray photoelectron spectra of cobalt and copper complexes with 2-{(E)-[2-(4-hydroxybutylami-no)benzimidazol-1-yl]iminomethyl}phenol,” Russian Journal of General Chemistry, vol. 88, no. 12, pp. 2550–2558, 2018.
• A. K. Satapathy, S. K. Behera, A. Yadav, L. N. Mahour, C. V. Yelamaggad, K. L. Sandhya, B. Sahoo, “Tuning the fluorescence behavior of liquid crystal molecules containing Schiff-base: Effect of solvent polarity,” Journal of Luminescence, vol. 210, pp. 371–375, 2019.
• B. Mohan, A. Jana, N. Das, S. Bharti, M. Choudhary, S. Muhammad, S. Kumar, A. G. Al-Sehemi, H. Algarni, “A dual approach to study the key features of nickel (II) and copper (II) coordination complexes: Synthesis, crystal structure, optical and nonlinear properties,” Inorganica Chimica Acta, vol. 484, pp. 148–159, 2019.
• E. W. Schmidt, “Hydrazine and Its Derivatives: Preparation, Properties, Applications,” John Wiley & Sons, 2nd ed., 2001.
• M. Yuan, D. B. Mitzi, “Solvent properties of hydrazine in the preparation of metal chalcogenide bulk materials and films,” Dalton Transactions, pp. 6078–6088, 2009.
• S. Basak, K. S. Rane, P. Biswas, “Hydrazine-assisted, low-temperature aerosol pyrolysis method to synthesize γ-Fe2O3,” Chemistry Materials, vol. 20, no. 15, pp. 4906–4914, 2008.
• R. Dennington II, T. Keith, J. Millam, Gauss View, Version 4.1.2, Semichem Inc, Shawnee Mission, KS, 2007.
• M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman Jr, J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson et al., Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford, CT, 2004.
• C. Lee, W. Yang, R. G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Physical Review B, vol. 37, pp. 785–789, 1988.
• M. J. Turner, J. J. MacKinnon, S. K. Wolff, D. J. Grimwood, P. R. Spackman, D. Jayatilaka, M. A. Spackman. Crystal explorer Ver. 17.5. University of Western Australia, 2017. http://hirshfeldsurface.net.
• Stoe & Cie X-AREA and X-RED32 , Stoe & Cie, Darmstadt, Germany, 2002.
• G. M. Sheldrick, “SHELXT - Integrated space-group and crystal-structure deter-mination,” Acta Crystallographica Section A: Foundations and Advances, vol. 71, pp. 3–8, 2015.
• G. M. Sheldrick, “Crystal Structure Refinement with SHELXL,” Acta Crystallographica Section C: Structural Chemistry, vol. 71, pp. 3–8, 2015.
• P. R. Spackman, M. J. Turner, J. J. McKinnon, S. K. Wolff, D. J. Grimwood, D. Jayatilaka, M. A. Spackman, “CrystalExplorer: A program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals,” Journal of Applied Crystallography, vol. 54, no. 3, pp. 1006-1011, 2021.
• M. A. Spackman, D. Jayatilaka, “Hirshfeld surface analysis,” Crystal Engineering Communication, vol. 11, pp. 19–32, 2009.
• O. Simsek, M. Dincer, N. Dege, E. Saif, I. Yilmaz, A. Cukurovali, “Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl) thiazol-2-yl] amino}-4-oxobut-2-enoic acid,” Acta Crystallographica Section E: Crystallographic Communications, vol. 78, no. 2, pp. 120–124, 2022.
• R. Yankova, I. Tankov, T. Tsaneva, “Crystal structure, intermolecular interactions and NLO properties for imidazolium hydrogen sulfate ionic liquid,” Journal of Molecular Structure, vol. 1273, pp. 134307, 2023.
• S. Atalay, M. Macit, H. Bulbul, “Crystal structure and computational studies of N-((2-ethoxynaphthalen-1-yl) methylene)-4-fluoroaniline,” European Journal of Chemistry, vol. 12, no. 4, pp. 454-458, 2021.
• M. N. Tahir, A. Ali, M. Khalid, M. Ashfaq, M. Naveed, S. Murtaza, I. Shafiq, M. A. Asghar, R. Orfali, S. Perveen, “Efficient synthesis of imine-carboxylic acid functionalized compounds: Single crystal, Hirshfeld surface and quantum chemical exploration,” Molecules, vol. 28, no. 7, pp. 2967, 2023.
• H. Gökce, F. Şen, Y. Sert, B. F. Abdel-Wahab, B. M. Kariuki, G. A. El-Hiti, “Quantum computational investigation of (E)-1-(4-methoxyphenyl)-5-methyl-N′-(3-phenoxybenzylidene)-1 H-1, 2, 3-triazole-4-carbohydrazide,” Molecules, vol. 27, no. 7, pp. 2193, 2022.
• G. Kaştaş, Ç. A. Kaştaş, “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 CH⋯ π) in their supramolecular architectures,” Journal of Molecular Structure, vol. 1184, pp. 427-434, 2019.
• M. R. Albayati, S. Kansız, H. Lgaz, S. Kaya, N. Dege, I. H. Ali, R. Salghi, I. M. Chung, “Synthesis, experimental and theoretical characterization of (E)-2-((2, 3-dimethylphenyl) amino)-N’-(furan-2-ylmethylene) benzohydrazide,” Journal of Molecular Structure, vol. 1219, pp. 128518, 2020.
• A. A. B. OmarAli, A. J. M. Al-Karawi, N. Dege, S. Kansız, H. A. Ithawi, "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," Journal of Molecular Structure, vol. 1217, pp. 128387, 2020.
• A. A. OmarAli, A. J. M. Al-Karawi, A. A. Awad, N. Dege, S. Kansız, E. Agar, Z. A. Hussein, I. R. Mohammed, "Two new zinc (II) and mercury (II) complexes based on N, N′-(cyclohexane-1, 2-diylidene) bis (4-fluorobenzohydrazide): synthesis, crystal structures and antibacterial activities," Acta Crystallographica Section C: Structural Chemistry, vol. 76, no. 5, pp. 476-482, 2020.
• R. Sathyanarayanan, M. Selvapandiyan, C. Senthilkumar, M. Srinivasan, P. Ramasamy, “Crystal growth, Hirshfeld surface, quantum chemical calculations, optical, photoluminescence and thermal analyses of sodium D-isoascorbate monohydrate single crystal,” Journal of Molecular Structure, vol. 1275, pp. 134637, 2023.
• A. Gannouni, W. Tahri, T. Roisnel, S. I. Al-Resayes, M. Azam, R. Kefi, “Single crystal investigations, Hirshfeld surface analysis, DFT studies, molecular docking, physico-chemical characterization, and biological activity of a novel non-centrosymmetric compound with a copper transition metal precursor,” ACS Omega, vol. 8, no. 8, pp. 7738-7748, 2023.
• J. Makhlouf, Y. El Bakri, A. Valkonen, K. Saravanan, S. Ahmad, W. Smirani, “Growth, single crystal investigations, hirshfeld surface analysis, DFT studies, molecular dynamics simulations, molecular docking, physico-chemical characterization and biological activity of novel thiocyanic complex with zinc transition metal precursor,” Polyhedron, vol. 222, pp. 115937, 2022.
• R. Saddik, S. A. Brandán, S. Mortada, C. Baydere, O. Roby, N. Dege, S. Tighadouini, M. Tahiri, M. A. Faouzi, K. Karrouchi, “Synthesis, crystal structure, Hirshfeld surface analysis, DFT and antihyperglycemic activity of 9-allyl-2, 3, 9, 10a-tetrahydrobenzo [b] cyclopenta [e][1, 4] diazepin-10 (1H)-one,” Journal of Molecular Structure, vol. 1283, pp. 135283, 2023.
• L. Guo, B. Tan, X. Zuo, W. Li, S. Leng, X. Zheng, “Eco-friendly food spice 2-Fur-furylthio-3-methylpyrazine as an excellent inhibitor for copper corrosion in sulfuric acid medium,” Journal of Molecular Liquids, vol. 317, 113915, 2020.
• Z. Demircioğlu, G. Kaştaş, Ç.A. Kaştaş, R. Frank, “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,” Journal of Molecular Structure, vol. 1191, pp. 129–137, 2019.
• H. Lgaz, R. Salghi, S. Masroor, S.H. Kim, C. Kwon, S.Y. Kim, Y.J. Yang, I.M. Chung, “Assessing corrosion inhibition characteristics of hydrazone derivatives on mild steel in HCl: insights from electronic-scale DFT and atomic-scale molecular dynamics,” Journal of Molecular Liquids, vol. 308, 112998, 2020.
• M. Azam, P.K. Sahoo, R.K. Mohapatra, M. Kumar, A. Ansari, I.S. Moon, A. Chutia, S.I. Resays, S.K. Biswal, “Structural investigations, Hirsfeld surface analyses, and molecular docking studies of a phenoxo-bridged binuclear zinc(II) complex,” Journal of Molecular Structure, vol. 1251, 132039, 2022.
• S. I. Al-Resayes, M. Azam, A. Trzesowska-Kruszynska, R. Kruszynski, S. M. Soliman, R. K. Mohapatra, Z. Khan, “Structural and theoretical investigations, Hirshfeld surface analyses, and cytotoxicity of a naphthalene-based chiral compound,” ACS Omega, vol. 5, pp. 27227–27234, 2020.
• A. Saeed, S. Ashraf, U. Flörke, Z. Y. D. Espinoza, M. F. Erben, H. Pérez, “Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis,” Journal of Molecular Structure, vol. 1111, pp. 76-83, 2016.
• S. Adhikari, A. H. Sheikh, S. Kansız, N. Dege, N. Baildya, G. Mahmoudi, N. A. Choudhury, R. J. Butcher, W. Kaminsky, S. Talledo, E. M. Lopato, S. Bernhard, J. Kłak, “Supramolecular Co (II) complexes based on dithiolate and dicarboxylate ligands: Crystal structures, theoretical studies, magnetic properties, and catalytic activity studies in photocatalytic hydrogen evolution,” Journal of Molecular Structure, pp. 135481, 2023.
• M. K. Gümüş, S. Kansiz, G. B. Tulemisova, N. Dege, E. Saif, “Crystal structure and Hirshfeld surface analysis of 3-(hydroxymethyl)-3-methyl-2, 6-diphenylpiperidin-4-one,” Acta Crystallographica Section E: Crystallographic Communications, vol. 78, no. 1, pp. 29-32, 2022.
• D. M. Al-thamili, A. I. Almansour, N. Arumugam, S. Kansız, N. Dege, S. M. Soliman, M. Azam, R. S. Kumar, “Highly functionalized N-1-(2-pyridinylmethyl)-3, 5-bis [(E)-arylmethylidene] tetrahydro-4 (1H)-pyridinones: Synthesis, characterization, crystal structure and DFT studies,” Journal of Molecular Structure, vol. 1222, pp. 128940, 2020.
• Z. Setifi, N. Cubillán, C. Glidewell, D. M. Gil, E. Torabi, M. Morales-Toyo, N. Dege, F. Setifi, M. Mirzaei, “A combined experimental, Hirshfeld surface analysis, and theoretical study on fac-[tri (azido)(tris (2-pyridyl) amine) iron (III)],” Polyhedron, vol. 233, pp. 116320, 2023.