Synthesis and Toxicity Test of Schiff Base Compound from 4-Formylpyridine and p¬-Anisidine Using Stirrer Method with Water Solvent
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Nov 3, 2021
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Abstract
Abstract- Schiff base is a compound that is produced when primary amine and aldehydes or ketones reacted under certain situations. Schiff base compounds have the characteristic of a C=N (imine) functional group. The Schiff base compound was synthesized from 4-formylpyridine and p-anisidine using a stirrer method with water as the solvent and a 15-minute synthesis time. FTIR spectrophotometer and GC-MS are being used to identify the product of Schiff base compound. The BSLT (Brine Shrimp Lethality Test) method has been used to test the toxicity and LC50 values are used as parameters for the toxic levels of Schiff base compound. The results showed the synthesis product have a yield 99.86%. The product of the synthesis of Schiff base compounds has a physical characteristics such as: greenish-gray solid with a melting point of 91-93.5 oC. The results of characterization using FTIR showed a typical absorption of the C=N group with the target compound at a wavenumber of 1620 cm-1. The results of the GC-MS characterization showed one signal with a retention time of 36.5 minutes and a 100% area. The molecular ion of the m/z was 212, which also corresponded to the molecular weight of the compound 4-methoxy-N-(pyridine-4-ylmethylene)aniline. The results of the toxicity test of Schiff's base compound using the BSLT (Bhrine Shrimp Lethality Test) method showed the presence of toxic properties that have potential as anti-cancer with an LC50 value of 18.66 ppm.
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ALFIN, Mohammad.
Synthesis and Toxicity Test of Schiff Base Compound from 4-Formylpyridine and p¬-Anisidine Using Stirrer Method with Water Solvent.
Proceedings of the International Conference on Green Technology, [S.l.], v. 11, n. 1, p. 33 - 36, nov. 2021.
ISSN 2580-7099.
Available at: <http://conferences.uin-malang.ac.id/index.php/ICGT/article/view/1399>. Date accessed: 19 apr. 2024.
doi: https://doi.org/10.18860/icgt.v11i1.1399.
Section
Chemistry
References
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[26] A.S. Abed, K.M. Ziadan, and A.Q. Abdullah, “Synthesis and Study Some Optical Properties of Conducting Polymer Poly p-Anisidine (PPANS) Doped with Camphor Sulphonic Acid (CSA)” Basrah Journal of Science, vol. 33, No 1A, pp.137-155, 2015.
[27] Mustofa “Toxicity Test of Schiff Base Compound of Synthesis Result from Vanilin and p-Anisidine,” Theses, Department of Chemistry, Faculty of Sains and Technology, State Islamic University (UIN) Maulana Malik Ibrahim Malang, 2019.
[28] Z.B. Laili, “Synthesis of Schiff Base Compound from 4-Formylpyridine and p-Toluidine Using Stirring Method (Water Solvent) and its Toxicity Test agains Artemia Salina L,” Theses, Department of Chemistry, Faculty of Sains and Technology, State Islamic University (UIN) Maulana Malik Ibrahim Malang, 2020.
[2] H.H. Abass, R.A. Salih, and A.A. Salih, “Synthesis, Characterization and Biological Activity of Two Phenol-Schiff Bases and Formaldehyde Resin Cobalt (II)-Complexes,” Global Journal of Pure and Applied Chemistry Research, vol. 3, No. 2, pp.14-23, July 2015.
[3] E.B. Poormohammadi, M. Behzad, Z. Abbasi, and S.D.A. Astaneh, “Copper Complexes of Pyrazolone-Based Schiff Base Ligands: Synthesis, Crystal Structures and Antibacterial Properties,” Journal of Molecular Structure, 1205, 127603, December 2019.
[4] Y. Xu, Y. Shi, F. Lei, and L. Dai, “A Novel and Green Cellulose-Based Schiff Base-Cu(II) Complex and its Excellent Antibacterial Activity,” Carbohydrate Polymers, 230, 115671, November 2019.
[5] L. Zhang, P. Yan, Y. Li, X. He, Y. Dai, and Z. Tan, “Preparation and Antibacterial Activity of a Cellulose-Based Schiff Base Derived from Dialdehyde Cellulose and L-Lysine,” Industrial Crops and Products, 145, 112126, January 2020.
[6] R.K. Mohapatra, A.K. Sarangi, M. Azam, M.M. El-ajaily, M. Kudrat-E-Zahan, S.B. Patjoshi, and 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, 1179, pp.65–75, October 2018.
[7] W.H. Mahmoud, R.G. Deghadi, and G.G. Mohamed, “Metal Complexes of Ferrocenyl-Substituted Schiff Base: Preparation, Characterization, Molecular Structure, Molecular Docking Studies, and Biological Investigation,” Journal of Organometallic Chemistry, 121113, January 2020.
[8] C.M. Sharaby, M.F. Amine, and A.A. Hamed, “Synthesis, structure characterization and biological activity of selected metal complexes of sulfonamide Schiff base as a primary ligand and some mixed ligand complexes with glycine as a secondary ligand,” Journal of Molecular Structure, 1134, pp.208–216, December 2016.
[9] R.S. Hunoor, B.R. Patil, D.S. Badiger, R.S. Vadavi, K.B. Gudasi, V.M. Chandrashekhar, and I.S. Muchchandi, “Spectroscopic, Magnetic and Thermal Studies of Co(II), Ni(II), Cu(II) and Zn(II) Complexes of 3-Acetylcoumarin–Isonicotinoylhydrazone and Their Antimicrobial and Anti-Tubercular Activity Evaluation,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 77, pp.838–844, August 2010.
[10] Y. Chen, Y. Mi, Q. Li, F. Dong, and Z. Guo, “Synthesis of Schiff Bases Modified Inulin Derivatives For Potential Antifungal and Antioxidant Applications,” International Journal of Biological Macromolecules, vol. 143, pp.714–723, September 2019.
[11] S. Shokrollahi, A. Amiri, F. Fadaei-Tirani, and K. Schenk-Joß, “Promising Anti-Cancer Potency of 4,5,6,7-Tetrahydrobenzo[D]Thiazole-Based Schiff-Bases,” Journal of Molecular Liquids, 300, 112262, December 2019.
[12] J. M. Dinore, A. A. Yelwande, M. P. Palve and A.V. Sapkal, 2016. Citric Acid Catalyzed Synthesis of Hydrazones Schiff Bases of 2,4-Dinitrophenyl Hydrazine. International Journal of Pharmacy & Pharmaceutical Research, vol. 6, No. 1, pp.349-354, April 2016.
[13] S. Shamim, S. Murtaza, and M.F. Nazar, “Synthesis of Schiff Bases of Pyridine-4-Carbaldehyde and their Antioxidant and DNA Binding Studies,” Journal of the Chemical Society of Pakistan, vol. 38, No. 3, January 2016.
[14] A.B. Thomas, P.N. Tupe, R.V. Badhe, R.K. Nanda, L.P. Kothapalli, O.D. Paradkar, P.A. Sharma and A.D. Deshpande, “Green Route Synthesis of Schiff's Bases of Isonicotinic Acid Hydrazide,” Green Chemistry Letters and Reviews, vol. 2, No. 1, pp.23-27, March 2009.
[15] V. K. Rao, S. S. Reddy, B. S. Krishna, K. R. M. Naidu, C. N. Raju and S. K. Ghosh, “Synthesis of Schiff's bases in aqueous medium: a green alternative approach with effective mass yield and high reaction rates,” Green Chemistry Letters and Reviews, vol. 3, No. 3, pp.217-223, September 2010.
[16] D. Bhai R., C.R. Girija, and R. Reddy K., “Green Synthesis of Novel Schiff Bases Derived from 2, 6 Diamino Pyridine-Characterization and Biological Activity,” Journal of Advances in chemistry, vol. 10, No. 5, pp.2705-2710, September 2014.
[17] U. Hasanah, A. Hanapi, and R. Ningsih, “Synthesis of Schiff Base Compound from Vanillin and p-Toluidine by Solvent Free-Mechanochemical Method,” In Proceedings of the International Conference on Green Technology, vol. 8, No. 1, pp.278-281, October 2017.
[18] S. Patil, S.D. Jadhav, M.B. Deshmukh and U.P. Patil, “Natural Acid Catalyzed Synthesis of Schiff under Solvent-Free Condition: As a Green Approach,” International Journal of Organic Chemistry, vol. 2, No. 2, pp.166-171, 2012.
[19] S. Bhagat, N. Sharma and T.S. Chundawat, “Synthesis of Some Salicylaldehyde-Based Schiff Bases in Aqueous Media,” Journal of Chemistry, vol. 2013, August 2012.
[20] Z. Zuraida, “Analisis Toksisitas Beberapa Tumbuhan Hutan dengan Metode Brine Shrimp Lethality Test (BSLT),” Jurnal Penelitian Hasil Hutan, vol. 36, No. 3, pp.239-246, November 2018.
[21] M.R. Hamidi, B. Jovanova, and T.K. Panovska, “Toxicоlogical Evaluation of The Plant Products Using Brine Shrimp (Artemia Salina L.) Model,” Maced pharm bull, vol. 60, No. 1, pp.9-18, April 2014.
[22] H.D. Salusu, E. Obeth, A.R. Zarta, E. Nurmarini, H. Nurkaya, I.W. Kusuma, and E.T. Arung, “The Toxicity and Antibacterial Properties of Calamus ornatus Bl,” Rattan Fruit. agriTECH, vol. 39, No. 4, pp.350-354, September 2019.
[23] M.F. Jasmarullah, “The Activity Test of Antioxidant and Toxicity Test of Schiff Base Compound from Vanilin and Aniline,” Theses, Department of Chemistry, Faculty of Sains and Technology, State Islamic University (UIN) Maulana Malik Ibrahim Malang, 2018.
[24] N. Millati, “Toxicity Test using BSLT Method of Steroid Compound in Petroleum ether Fraction from Microalgae Chlorella sp.,” Theses, Department of Chemistry, Faculty of Sains and Technology, State Islamic University (UIN) Maulana Malik Ibrahim Malang, 2016.
[25] A. Saglam, F. Ucun, and V. Guclu, “Molecular Structures and Vibrational Frequencies 2,3 and 4-Pyridinecarboxaldehydes by Abinition Hartree Fock and Density Functional Theory Calculations,” Spectrochimica Acta Part A: Moleculer and Biomolecular Spectroscopy, vol. 67, No. 2, pp.465-471, August 2007.
[26] A.S. Abed, K.M. Ziadan, and A.Q. Abdullah, “Synthesis and Study Some Optical Properties of Conducting Polymer Poly p-Anisidine (PPANS) Doped with Camphor Sulphonic Acid (CSA)” Basrah Journal of Science, vol. 33, No 1A, pp.137-155, 2015.
[27] Mustofa “Toxicity Test of Schiff Base Compound of Synthesis Result from Vanilin and p-Anisidine,” Theses, Department of Chemistry, Faculty of Sains and Technology, State Islamic University (UIN) Maulana Malik Ibrahim Malang, 2019.
[28] Z.B. Laili, “Synthesis of Schiff Base Compound from 4-Formylpyridine and p-Toluidine Using Stirring Method (Water Solvent) and its Toxicity Test agains Artemia Salina L,” Theses, Department of Chemistry, Faculty of Sains and Technology, State Islamic University (UIN) Maulana Malik Ibrahim Malang, 2020.