Yıl: 2020 Cilt: 10 Sayı: 1 Sayfa Aralığı: 179 - 188 Metin Dili: İngilizce DOI: 10.37094/adyujsci.633080 İndeks Tarihi: 13-12-2021

Preparation and Characterization of Some Schiff Base Compounds

Öz:
Schiff bases (imines) have been frequently used in various fields such as medicine, pharmaceutical purposes due to their various biological properties. In this study, nine new imine compounds (3a-h) were synthesized from 1-naphthyl amine with aromatic aldehydes in MeOH and their chemical structures were defined by 1H/13C NMR, IR and elemental analysis studies. We observed a singlet one hydrogen of the imines (–CH=N–) at 8.56–8.86 ppm in the 1H NMR spectra and also carbon of the Schiff bases (–CH=N–) at 158.2-163.4 ppm in the 13C NMR spectra. Also the IR spectra displayed the (–C=N–) characteristic absorption band at around 1600 cm -1 . The obtained characteristic peaks at the expected locations proved the structural accuracy of the synthesized new derivative Schiff bases. Keywords: Schiff bases; Imines; 2-naphthylamine; Aromatic Aldehyde.
Anahtar Kelime:

Bazı Schiff Baz Bileşiklerinin Hazırlanması ve Karakterizasyonu

Öz:
Schiff bazları (iminler), çeşitli biyolojik özellikleri nedeniyle tıp, farmasötik amaçlar gibi çeşitli alanlarda sıkça kullanılmaktadır. Bu çalışmada, 1-naftil aminden MeOH içerisinde aromatik aldehitler ile dokuz yeni imin bileşiğinin (3a-h) sentezi yapılarak ve kimyasal yapıları; 1H/13C NMR, IR ve elemantel analiz yöntemleri aydınlatılmıştır. 1H/13C NMR analiz sonuçları incelendiğinde iminlerin (–CH=N–) protonu 8.56-8.86 ppm ve karbonunun ise 158.2-163.4 ppm de geldiği gözlemlenmiştir. Ayrıca IR spektrumundada (–C=N–) piki 1600 cm -1 civarında görülmüştür. Elde edilen bu karakteristik piklerin beklenen yerlerde gelmesi sentezlenen yeni türev Shifft bazların yapısal doğruluğunu kanıtlamıştır. Anahtar Kelimeler: Schiff bazları; İminler; 2-naftilamin; Aromatik aldehit.
Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • Schiff, H., Untersuchungen über salicinderivate, Justus Liebigs Annalen der Chemie, 150 (2), 193-200, 1869.
  • Patel, P.R., Thaker, B.T., Zele, S., Preparation and characterisation of some lanthanide complexes involving a heterocyclic β–diketone, NISCAIR-CSIR, India, 38A(6), 563-567, 1999.
  • Berg, M.A., The bromine addition products of the schiff bases, Bulletin de la Societe Chimique de France, 37, 637-641, 1925.
  • Hania, M.M., Synthesis of some imines and investigation of their biological activity, Journal of Chemistry, 6(3), 629-632, 2009.
  • Cohen, A.B., The interaction of α-1-antitrypsin with chymotrypsin, trypsin and elastase, Biochimica et Biophysica Acta (BBA)-Enzymology, 391(1), 193-200, 1975.
  • Badwaik, V.B., Deshmukh, R.D., Aswar A.S., Transition metal complexes of a schiff base: synthesis, characterization, and antibacterial studies, Journal of Coordination Chemistry, 62(12), 2037-2047, 2009.
  • Hussain, Z., Yousif, E., Ahmed, A., Altaie, A., Synthesis and characterization of schiff's bases of sulfamethoxazole, Organic and Medicinal Chemistry Letters, 4(1), 1, 2014.
  • Yamada, S., Advancement in stereochemical aspects of schiff base metal complexes, Coordination Chemistry Reviews, 190, 537-555, 1999.
  • Sharaby, C.M., Amine, M.F., Hamed, A.A., 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, 208-216, 2017.
  • Abbaspour, A., Esmaeilbeig, A.R., Jarrahpour, A.A., Khajeh, B., Kia, R., Aluminium (III)-selective electrode based on a newly synthesized tetradentate schiff base, Talanta, 58(2), 397-403, 2002.
  • Pfeiffer, P., Breith, E., Lubbe, E., Tsumaki, T., Tricyclische orthokondenzierte nebenvolenzringe, Annalen der Chemie, 503, 84-127, 1933.
  • Redshaw, C., Use of metal catalysts bearing schiff base macrocycles for the ring opening polymerization (ROP) of cyclic esters, Catalysts, 7(5), 165-176, 2017.
  • Tiwari, V., Meshram, J., Ali, P., Microwave assisted synthesis of of quinolinyl thiazolidinones using zeolite as an efficient and recyclable activation surface: SAR and biological activity, Der Pharma Chemica, 2(3), 187-195, 2010.
  • Mistry, K.M., Desai, K.R., Synthesis of novel heterocyclic 4-thiazolidinone derivatives and their antibacterial activity, Journal of Chemistry, 1(4), 189-193, 2004.
  • Hania, M.M., Synthesis of some imines and investigation of their biological activity, Journal of Chemistry, 6(3), 629-632, 2009.
  • Movrin, M., Maysinger, D., Biologically active n-mannich bases of isatin-3-(phenyl)- imines (author's transl), Die Pharmazie, 34(9), 535-536, 1979.
  • Abdulghani, J.A., Nada, M.A., Synthesis characterization and biological activity study of new schiff and mannich bases and some metal complexes derived from isatin and dithiooxamide, Bioinorganic Chemistry and Applications, 2011, 15, 2011.
  • Ebrahimi, H., Hadi, J.S., Al-Ansari, H.S., A new series of schiff bases derived from sulfa drugs and indole-3-carboxaldehyde: synthesis, characterization, spectral and DFT computational studies, Journal of Molecular Structure, 1039, 37-45, 2013.
  • Nafia, R.A., Fadhil, L.F., Synthesis and characterization of new indole schiff bases and study effect of the compounds on lymphatic cell in metaphase in human blood, Journal of Pharmaceutical Sciences and Research, 11(4), 1319-1326, 2019.
  • Berber, N., Arslan, M., Bilen, Ç, Sackes, Z., Gençer, N., Arslan, O., Synthesis and evaluation of new phthalazine substituted β-lactam derivatives as carbonic anhydrase inhibitors, Russian Journal of Bioorganic Chemistry, 41(4), 414-420, 2015.
  • Turan, B., Şendil, K., Şengül, E., Gültekin, M.S., Taslimi, P., Gulcin, I., Supuran, C.T., The synthesis of some β-lactams and investigation of their metal-chelating activity, carbonic anhydrase and acetylcholinesterase inhibition profiles, Journal of Enzyme Inhibition and Medicinal Chemistry, 31(sup1), 79-88, 2016.
  • Ostrowski, S., Wolniewicz, A.M., An approach to fused pyrimidine derivativesvia schiff bases of aromaticortho-nitrocarbaldehydes. An investigation of substituent effects on the reaction course, Chemistry of Heterocyclic Compounds, 36(6), 705-713, 2000.
  • Woodward, R.B., Heusler, K., Gosteli, J., Naegeli, P., Oppolzer, W., Ramage, R., Ranganathan, S., Vorbrüggen, H., The total synthesis of cephalosporin C1 , Journal of the American Chemical Society, 88(4), 852-853, 1966.
  • Marcantoni, E., Palmieri, A., Petrini, M., Recent synthetic applications of α-amido sulfones as precursors of n-acylimino derivatives, Organic Chemistry Frontiers, 6(13), 2142- 2182, 2019.
  • Elmacı, G., Duyar, H., Aydıner, B., Yahaya, I., Seferoglu, N., Sahin, E., Çelik, S.P., Açık, L., Seferoglu, Z., Novel benzildihydrazone based schiff bases: syntheses, characterization, thermal properties, theoretical DFT calculations and biological activity studies, Journal of Molecular Structure, 1184, 271-280, 2019.
  • Elmacı, G., Duyar, H., Aydıner, B., Seferoglu, N., Naziri, M.A., Sahin, E., Seferoglu, Z., The syntheses, molecular structure analyses and DFT studies on new benzil monohydrazone based schiff bases, Journal of Molecular Structure, 1162, 37-44, 2018.
  • Elmacı, G., Aktan, E., Seferoglu, N., Hökelek, T., Seferoglu, Z., Synthesis, molecular structure and computational study of (Z)-2-((E)-4-nitrobenzylidene) hydrazone)-1, 2-
  • Beck, J.F., Ortho metallated acetophenone imines as ligands for transition and main group metals: synthesis and organometallic reactivity and the hydroamination of allenes using a palladium allyl triflate 3-iminophosphine precatalyst, Diss. University of Toledo, 2011.
  • Shelke, V.A., Jadhav, S.M., Patharkar, V.R., Shankarwar, S.G., Munde, A.S., Chondhekar, T.K., Synthesis, spectroscopic characterization and thermal studies of some rare earth metal complexes of unsymmetrical tetradentate schiff base ligand, Arabian Journal of Chemistry. 5(4), 501-507, 2012.
  • Xu, J., Zhuang, R., Bao, L., Tang, G., Zhao, Y., KOH-mediated transition metal-free synthesis of imines from alcohols and amines, Green Chemistry, 14(9), 2384-2387, 2012.
  • Kozlov, N.G., Basalaeva, L.I., Skakovskaya, E.Y., Synthesis of benzo [a] phenanthridine derivatives by condensation of n-arylmethylene-2-naphthylamines with 5-phenyland-5-(p-Methoxyphenyl)-1, 3-cyclohexanediones, Russian Journal of General Chemistry, 72(8), 1238-1242, 2002.
  • Blackburn, L., Taylor, R.J., In situ oxidation imine formation reduction routes from alcohols to amines, Organic Letters, 3(11), 1637-1639, 2001.
  • Vázquez, M.Á., Landa, M., Reyes, L., Miranda, R., Tamariz, J., Delgado, F., Infrared irradiation: effective promoter in the formation of n‐benzylideneanilines in the absence of solvent, Synthetic Communications, 34(15), 2705-2718, 2004.
  • Goszczyńska, A., Kwiecień, H., Fijałkowski, K., Synthesis and antibacterial activity of schiff bases and amines derived from alkyl 2-(2-formyl-4-nitrophenoxy) alkanoates, Medicinal Chemistry Research, 24(9), 3561-3577, 2015.
  • Sharma, S., Singh, T., Mittal, R., Saxena, K.K., Srivastava, V.K., Kumar, A., A study of anti‐inflammatory activity of some novel α‐amino naphthalene and β‐amino naphthalene derivatives, Archiv der Pharmazie: An International Journal Pharmaceutical and Medicinal Chemistry, 339(3), 145-152, 2006.
  • Arora, K., Parmar, A., Simulation of IR spectra of some organic compounds-a review, IOSR Journal of Applied Chemistry (IOSR-JAC), 6(1), 10-24, 2013.
  • Kozlov, N.G., Yakubovich, L.S., Murashko, V.L., Condensation of ethyl cydopentanone-2-carboxylate with N-arylmethylene-2-naphthylamines, Russian Journal of Electrochemistry, 36(6), 777-780, 2000.
  • Güngör, Ö.Ö., Intramolecular proton transfer equilibrium in salicylidene-and naphthalene-based tetraimine schiff base, Gazi University Journal of Science, 30(1), 191-214, 2017.
APA Berber N, ARSLAN M (2020). Preparation and Characterization of Some Schiff Base Compounds. , 179 - 188. 10.37094/adyujsci.633080
Chicago Berber Nurcan,ARSLAN Mustafa Preparation and Characterization of Some Schiff Base Compounds. (2020): 179 - 188. 10.37094/adyujsci.633080
MLA Berber Nurcan,ARSLAN Mustafa Preparation and Characterization of Some Schiff Base Compounds. , 2020, ss.179 - 188. 10.37094/adyujsci.633080
AMA Berber N,ARSLAN M Preparation and Characterization of Some Schiff Base Compounds. . 2020; 179 - 188. 10.37094/adyujsci.633080
Vancouver Berber N,ARSLAN M Preparation and Characterization of Some Schiff Base Compounds. . 2020; 179 - 188. 10.37094/adyujsci.633080
IEEE Berber N,ARSLAN M "Preparation and Characterization of Some Schiff Base Compounds." , ss.179 - 188, 2020. 10.37094/adyujsci.633080
ISNAD Berber, Nurcan - ARSLAN, Mustafa. "Preparation and Characterization of Some Schiff Base Compounds". (2020), 179-188. https://doi.org/10.37094/adyujsci.633080
APA Berber N, ARSLAN M (2020). Preparation and Characterization of Some Schiff Base Compounds. Adıyaman Üniversitesi Fen Bilimleri Dergisi, 10(1), 179 - 188. 10.37094/adyujsci.633080
Chicago Berber Nurcan,ARSLAN Mustafa Preparation and Characterization of Some Schiff Base Compounds. Adıyaman Üniversitesi Fen Bilimleri Dergisi 10, no.1 (2020): 179 - 188. 10.37094/adyujsci.633080
MLA Berber Nurcan,ARSLAN Mustafa Preparation and Characterization of Some Schiff Base Compounds. Adıyaman Üniversitesi Fen Bilimleri Dergisi, vol.10, no.1, 2020, ss.179 - 188. 10.37094/adyujsci.633080
AMA Berber N,ARSLAN M Preparation and Characterization of Some Schiff Base Compounds. Adıyaman Üniversitesi Fen Bilimleri Dergisi. 2020; 10(1): 179 - 188. 10.37094/adyujsci.633080
Vancouver Berber N,ARSLAN M Preparation and Characterization of Some Schiff Base Compounds. Adıyaman Üniversitesi Fen Bilimleri Dergisi. 2020; 10(1): 179 - 188. 10.37094/adyujsci.633080
IEEE Berber N,ARSLAN M "Preparation and Characterization of Some Schiff Base Compounds." Adıyaman Üniversitesi Fen Bilimleri Dergisi, 10, ss.179 - 188, 2020. 10.37094/adyujsci.633080
ISNAD Berber, Nurcan - ARSLAN, Mustafa. "Preparation and Characterization of Some Schiff Base Compounds". Adıyaman Üniversitesi Fen Bilimleri Dergisi 10/1 (2020), 179-188. https://doi.org/10.37094/adyujsci.633080