SYNTHESIS, STRUCTURAL AND THEORETICAL INVESTIGATION OF SOME NEW SCHIFF BASES AND 1,3,4-OXADIAZOLE COMPOUNDS DERIVED FROM LAURIC ACID
Abstract
New Schiff bases derivatives from lauric acid were synthesized through the condensation of dodecane methyl ester with hydrazine to give corresponding hydrazide, which react with aromatic aldehyde derivatives to afford dodecanehydrazide-hydrazones derivatives and with carbon disulfide to give 1,3,4-oxadiazole-2-thion. The chemical structures were confirmed by numerous characterization methods; including Infrared, Ultraviolet-Visible, 1H and 13C Nuclear Magnetic Resonance (NMR) measurements. In order to investigate the 1H and 13C Nuclear Magnetic Resonance, vibrational frequencies, Ultraviolet visible spectra, optimized molecular geometry, HOMO & LUMO and other spectroscopic properties, Density Functional Theory (DFT/B3LYP/6-311++G(d,p)) stimulations were carried out
Downloads
References
Abdulghani, A.J. and Abbas, N.M. (2011) ‘Synthesis Characterization and Biological Activity Study of New Schiff and Mannich Bases and Some Metal Complexes Derived from Isatin and Dithiooxamide’, 2011. Available at: https://doi.org/10.1155/2011/706262.
Aggoun, D. et al. (2021) ‘Synthesis , characterization and DFT investigation of new metal complexes of Ni ( II ), Mn ( II ) and VO ( IV ) containing N , O-donor Schiff base ligand’, Journal of Molecular Structure, 1231, p. 129923. Available at: https://doi.org/10.1016/j.molstruc.2021.129923.
Agregán, R. et al. (2022) ‘Fatty acids’, Food Lipids: Sources, Health Implications, and Future Trends, pp. 257–286. Available at: https://doi.org/10.1016/B978-0-12-823371-9.00015-0.
Aidi, M. et al. (2018) ‘Pharmaceutical sciences research center , Kermanshah University of Medical Sciences , School of Chemistry , University of Melbourne , Victoria 3010 , Australia’, Inorganica Chimica Acta [Preprint], (Ii). Available at: https://doi.org/10.1016/j.ica.2018.12.046.
Belaidi, O., Bouchaour, T. and Maschke, U. (2014) ‘The molecular conformation of butyl acrylate - A vibrational spectroscopy and computational study’, Vibrational Spectroscopy, 73, pp. 56–66. Available at: https://doi.org/10.1016/j.vibspec.2014.04.004.
Bendre, R.S., Tadavi, S.K. and Patil, M.M. (2017) ‘Synthesis , crystal structures and biological activities of transition metal complexes of a salen ‑ type ligand’, Transition Metal Chemistry [Preprint]. Available at: https://doi.org/10.1007/s11243-017-0196-y.
Brahmkhatri, V. and Patel, A. (2012) ‘Esterification of lauric acid with butanol-1 over H 3PW 12O 40 supported on MCM-41’, Fuel, 102, pp. 72–77. Available at: https://doi.org/10.1016/j.fuel.2012.05.053.
Carpenter, C.A., Kenar, J.A. and Price, N.P.J. (2010) ‘Preparation of saturated and unsaturated fatty acid hydrazides and long chain C-glycoside ketohydrazones’, Green Chemistry, 12(11), pp. 2012–2018. Available at: https://doi.org/10.1039/c0gc00372g.
Elmacı, G. et al. (2019) ‘SC’, Journal of Molecular Structure [Preprint]. Available at: https://doi.org/10.1016/j.molstruc.2019.01.104.
Fahim, A.M. et al. (2021) ‘Synthesis of novel β-lactams: Antioxidant activity, acetylcholinesterase inhibition and computational studies’, Journal of Molecular Structure, 1233. Available at: https://doi.org/10.1016/j.molstruc.2021.130092.
Faraj, F.L. et al. (2019) ‘Synthesis of New Indole Schiff Bases and Evaluation of Their Biological Activity on Lymphatic Cell in Metaphase in Human Blood’, Biochemical and Cellular Archives, 19(2), pp. 4517–4524. Available at: https://doi.org/10.35124/bca.2019.19.2.4517.
Fukui, K. (1981) ‘Fukui-Lecture.Pdf’.
Gökce, H. et al. (2017) ‘Structural, spectroscopic, electronic, nonlinear optical and thermodynamic properties of a synthesized Schiff base compound: A combined experimental and theoretical approach’, Journal of Molecular Structure, 1136, pp. 288–302. Available at: https://doi.org/10.1016/j.molstruc.2017.01.089.
Hiremath, S.M. et al. (2018) ‘Synthesis of 5-(5-methyl-benzofuran-3-ylmethyl)-3H- [1, 3, 4] oxadiazole-2-thione and investigation of its spectroscopic, reactivity, optoelectronic and drug likeness properties by combined computational and experimental approach’, Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 205, pp. 95–110. Available at: https://doi.org/10.1016/j.saa.2018.07.003.
January, R. (2013) ‘Dinucleating Schiff base ligand in Zn / 4f coordination chemistry : Synthetic challenges and catalytic activity evaluation’, 2(3), pp. 1–3. Available at: https://doi.org/10.1039/x0xx00000x.
Kajal, A. et al. (2013) ‘Schiff Bases : A Versatile Pharmacophore’, 2013(Mic).
Kargar, H. et al. (2021) ‘Ultrasound-based synthesis , SC-XRD , NMR , DFT , HSA of new Schiff bases derived from 2-aminopyridine : Experimental and theoretical studies’, Journal of Molecular Structure, 1233, p. 130105. Available at: https://doi.org/10.1016/j.molstruc.2021.130105.
Liu, X. et al. (2018) ‘Multidentate unsymmetrically-substituted Schiff bases and their metal complexes : Synthesis , functional materials properties , and applications to catalysis’, Coordination Chemistry Reviews, 357, pp. 144–172. Available at: https://doi.org/10.1016/j.ccr.2017.11.030.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G.E.S. et al. (2015) ‘Gaussian 09, Revision D.01’.
Maniak, H. et al. (2020) ‘Synthesis and structure-activity relationship studies of hydrazide-hydrazones as inhibitors of laccase from trametes versicolor’, Molecules, 25(5). Available at: https://doi.org/10.3390/molecules25051255.
Nabhan, K.J. et al. (2022) ‘New tetra-dentate schiff base ligand N2O2 and its complexes with some of metal ions: preparation, identification, and studying their enzymatic and biological activities’, Baghdad Science Journal, 19(1), pp. 155–167. Available at: https://doi.org/10.21123/BSJ.2022.19.1.0155.
Orr, S.A., Andrews, P.C. and Blair, V.L. (2021) ‘Main Group Metal-Mediated Transformations of Imines’, Chemistry - A European Journal, 27(8), pp. 2569–2588. Available at: https://doi.org/10.1002/chem.202003108.
Özdemir Tari, G., Gümüş, S. and Aʇar, E. (2015) ‘Crystal structure, spectroscopic studies and quantum mechanical calculations of 2-[((3-iodo-4-methyl)phenylimino)methyl]-5-nitrothiophene’, Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 141, pp. 119–127. Available at: https://doi.org/10.1016/j.saa.2015.01.050.
Parveen, S. (2020) ‘Recent advances in anticancer ruthenium Schiff base complexes’, Applied Organometallic Chemistry, 34(8), pp. 1–23. Available at: https://doi.org/10.1002/aoc.5687.
Qin, J.C. and Yang, Z.Y. (2016) ‘Fluorescent chemosensor for detection of Zn2+ and Cu2+ and its application in molecular logic gate’, Journal of Photochemistry and Photobiology A: Chemistry, 324, pp. 152–158. Available at: https://doi.org/10.1016/j.jphotochem.2016.03.029.
Qin, W. et al. (2013) ‘Schiff Bases: A Short Survey on an Evergreen Chemistry Tool’, (April 1834), pp. 12264–12289. Available at: https://doi.org/10.3390/molecules181012264.
Raczuk, E. et al. (2022) ‘Different Schiff Bases—Structure, Importance and Classification’.
Rosaleen J. Anderson, D.J.B. and P.W.G. (2010) Organic Spectroscopic Analysis, Antimicrobial Agents and Chemotherapy. Available at: http://www.ncbi.nlm.nih.gov/pubmed/25246403%0Ahttp://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=PMC4249520%0Ahttp://aac.asm.org/lookup/doi/10.1128/AAC.03728-14%0Ahttp://arxiv.org/abs/1011.1669%0Ahttp://dx.doi.org/10.1088/1751-8113/44/8/085201.
Sherif, O.E. and Abdel-kader, N.S. (2015) ‘DFT calculations , spectroscopic studies , thermal analysis and biological activity of supra molecular Schiff base complexes’, ARABIAN JOURNAL OF CHEMISTRY [Preprint]. Available at: https://doi.org/10.1016/j.arabjc.2015.07.008.
Singh, G. et al. (2021) ‘A quick microwave preparation of isatin hydrazone schiff base conjugated organosilicon compounds : Exploration of their antibacterial , antifungal , and antioxidative potentials’, Journal of Organometallic Chemistry, 953, p. 122051. Available at: https://doi.org/10.1016/j.jorganchem.2021.122051.
Singh, N., Ranjana, R. and Kumari, M. (2016) ‘A Review on Biological Activities of Hydrazone Derivatives’, 8(3), pp. 162–166.
Singh, R.K. et al. (2017) ‘Synthesis, molecular structure, spectral analysis and cytotoxic activity of two new aroylhydrazones’, Journal of Molecular Structure, 1135, pp. 82–97. Available at: https://doi.org/10.1016/j.molstruc.2017.01.059.
Sıcak, Y. et al. (2019) ‘Novel fluorine-containing chiral hydrazide-hydrazones: Design, synthesis, structural elucidation, antioxidant and anticholinesterase activity, and in silico studies’, Chirality, 31(8), pp. 603–615. Available at: https://doi.org/10.1002/chir.23102.
Srivastava, K.P., Yadav, U.S. and Singh, P. (2021) ‘EVALUATION OF ANTIMICROBIAL ACTIVITIES OF MICROWAVE-IRRADIATION SYNTHESIZED TETRADENTATE ( N 2 O 2 DONOR ) SCHIFF BASE AND ITS Cu ( II ) COMPLEXES’, 14(4), pp. 2604–2612.
Su, X. et al. (2013) ‘Manipulating Liquid-Crystal Properties Using a pH Activated Hydrazone Switch’, Angewandte Chemie, 125(41), pp. 10934–10939. Available at: https://doi.org/10.1002/ange.201305514.
Tidwell, T.T. (2008) ‘Hugo ( Ugo ) Schiff , Schiff Bases , and a Century of b -Lactam Synthesis **’, pp. 1016–1020. Available at: https://doi.org/10.1002/anie.200702965.
Turan, B. et al. (2016) ‘The synthesis of some β -lactams and investigation of their metal-chelating activity , carbonic anhydrase and acetylcholinesterase inhibition profiles’, 6366. Available at: https://doi.org/10.3109/14756366.2016.1170014.
Wu, B.X. et al. (2021) ‘Synthesis, photochemical isomerization and photophysical properties of hydrazide-hydrazone derivatives’, New Journal of Chemistry, 45(3), pp. 1651–1657. Available at: https://doi.org/10.1039/d0nj05172a.
Wu, J. et al. (2021) ‘Synthesis and Cytotoxic Activity of Novel Betulin Derivatives Containing Hydrazide-Hydrazone Moieties’, Natural Product Communications, 16(10), pp. 4–10. Available at: https://doi.org/10.1177/1934578X211055345.
Yang, Z.B., Li, P. and He, Y.J. (2020) ‘Novel pyrethrin derivatives containing hydrazone and 1,3,4-oxadiazole thioether moieties: Design, synthesis, and insecticidal activity’, Phosphorus, Sulfur and Silicon and the Related Elements, 195(8), pp. 614–619. Available at: https://doi.org/10.1080/10426507.2019.1700416.
Zhang, Y., Xu, X. and Goddard, W.A. (2009) ‘Doubly hybrid density functional for accurate descriptions of nonbond interactions, thermochemistry, and thermochemical kinetics’, Proceedings of the National Academy of Sciences of the United States of America, 106(13), pp. 4963–4968. Available at: https://doi.org/10.1073/pnas.0901093106.
Zhou, B. et al. (2009) ‘Study on THz spectrum of artemeter’, Journal of Molecular Structure, 919(1–3), pp. 325–327. Available at: https://doi.org/10.1016/j.molstruc.2008.09.025.
It is the policy of the Journal of Duhok University to own the copyright of the technical contributions. It publishes and facilitates the appropriate re-utilize of the published materials by others. Photocopying is permitted with credit and referring to the source for individuals use.
Copyright © 2017. All Rights Reserved.



