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2-Amino-6-sübstitüepiridin Türevleri ile 5-Sülfosalisilik Asitin Zn(II) Komplekslerinin Sentezi ve Karakterizasyonu

Yıl 2024, Cilt: 50 Sayı: 2, 43 - 48, 01.10.2024

Halil İlkimen , Cengiz Yenikaya , Zeynep Alkan Alkaya

https://doi.org/10.35238/sufefd.1454696

Öz

Bu çalışmada, dört yeni Zn(II) kompleksleri {(HX)2[Zn(Hssal)2(H2O)2], H3ssal: 5-sülfosalisilik asit, X = 5 için 2-amino-6-metilpiridin (1), 6 için 2-amino-3-etil-6-metilpiridin (2) ve 7 için 2-amino-3-nitro-6-metilpiridin (3)} ve {[Zn(Hssal)(X)2(H2O)2] {X = 8 için 2-amino-3-nitro-6-kloropiridin (4)} elde edildi. Zn(II) komplekslerinin yapıları element analizi, AAS, FT-IR, molar iletkenlik ve manyetik duyarlılık analizleri ile karakterize edildi. IR ve iletkenlik analizleri sonucunda 5-7 metal komplekslerinin iyonik olduğu ve 8 metal kompleksinin ise iyonik olmadığı gözlenmiştir. Bu sonuçları AAS ve elementel analiz testleri de desteklemektedir. Manyetik duyarlılık çalışmalarında Zn(II) (d10) metal komplekslerinin beklendiği gibi eşleşmemiş elektron taşımadıkları gözlenmiştir. Yapılan spektroskopik analiz sonuçlarında tüm komplekslerin (5-8) oktahedral yapıya sahip oldukları önerilmiştir.

Anahtar Kelimeler

5-Sülfosalisilik asit 2-Aminopiridin Zn(II) kompleksi Oktahedral yapı

Kaynakça

  • Banowski, B., Kropf, C., (2015), Cosmetic antiperspirants with aromatic sulphonic acids. Germany, DE102013220789 A1 2015-04-16a.
  • Banowski, B., Kropf, C., (2015), Cosmetic antiperspirants with aromatic sulphonic acids. World Intellectual Property Organization, WO2015055198 A1 2015-04-23b.
  • Buyukkidan, N., Yenikaya, C., Ilkimen, H., Karahan, C., Darcan, C., Şahin, E., (2013), Synthesis, characterization and antimicrobial activity of a novel proton salt and its Cu(II) complex. Russian Journal of Coordination Chemistry, 39(1), 96-103.
  • Chen, Z. F., Shi, S. M., Hu, R. X., Zhang, M., Liang, H., Zhou, Z. Y., (2003), Synthesis, crystal structure, fluorescence property and antibacterial activity of two unprecedented one-dimensional chain metalorganic coordination polymers: Zn(H-SSA)(Phen)(H2O)2 and Cu(H-SSA)(Phen)(H2O)2. Chinese Journal of Chemistry, 21(8), 1059-1065.
  • Cook, D., (1961), Vibrational spectra of pyridinium salts. Canadian Journal of Chemistry, 39(10), 2009-2024.
  • Du, Z. X., Li, J. X., Wang, L. Y., (2009), Syntheses, crystal structures and fluorescent properties of two 4,4'-dipyridylsulfide based zinc(II) and cadmium(II) helical complexes. Journal of Coordination Chemistry, 62(15), 2411-2420.
  • Duan, X., Li, D., Lin, Y., Zhang, L., Tuo, Z., (2006), Method for preparing layered double hydroxides-sulfosalicylic acid having supramol İntercalating structure and its application. China, CN1861702 A 2006-11-15.
  • Fan, S. R., Zhu, L. G., Xiao, H. P., (2005), catena-Poly[[cis-diaqua(2,2'-bipyridine)zinc(II)]-μ-5-sulfonatosalicylato]. Acta Crystallographica, E61(5), m804-m806.
  • Geary, W. J., (1971), The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coordination Chemistry Reviews, 7, 81-122.
  • Han, Q., Wang, X. C., Li, X. Y., Yao, G. X., Yan, Y. S., (2009), Aqua(2-hydroxy-5-sulfonatobenzoato-κO1)bis(2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene-κ2N7,N8)zinc(II). Acta Crystallographica, E65(11), m1282-m1283.
  • Hecht, E., (2004), catena-Poly[[tetraaquazinc(II)]-μ-5-sulfosalicylato-κ2O:O'] Acta Crystallographica, E60(9), m1286-m1288.
  • Heleno, S. A., Martins, A., Queiroz, M. J. R. P, Ferreira, I. C. F. R., (2015), Bioactivity of phenolic acids: metabolites versus parent compounds: a review. Food Chemistry, 173, 501-513.
  • Ilkimen, H., İlkimen, B., Yenikaya, C., (2022), Metal complexes of 5-sulfosalicylic acid. New developments in science and mathematics, Bölüm 2.3, ss 221-234, Hiperyayın Evi.
  • Ivanova, B., Spiteller, M., (2017), On the nature of the coordination bonding of metal-organics for ions with the d10 electronic configuration - Experimental and theoretical analyses. Polyhedron, 137, 256-264.
  • Khadikar, P. V., Joshi, S., Kashkhedikar, S. G., Heda, B. D., (1984), Metal-complexes of 5-sulfosalicylic acid and their antimicrobial activity. Indian Journal of Pharmaceutical Sciences, 46(6), 209-211.
  • Koksharova, T., Slyvka, Y., Savchenko, O., Mandzii, T., Smola, S., (2023), 5-Sulfosalicylato Cu(II), Zn(II) and Ni(II) coordination compounds with benzohydrazide: Synthesis, structure and luminescent properties. Journal of Molecular Structure, 1271, 133980.
  • Lamshoeft, M., Storp, J., Ivanova, B., Spiteller, M., (2011), Gas-phase CT-stabilized Ag(I) and Zn(II) metal-organic complexes - Experimental versus theoretical study. Polyhedron, 30(15), 2564-2573.
  • Ma, J. F., Yang, J., Liu, J. F., (2003), Hexaaquazinc(II) 3-carboxy-4-hydroxybenzenesulfonate tetrahydrate. Acta Crystallographica, E59(7), m487-m488.
  • Ma, W. X., Qian, B. H., Gao, J., Xu, X. Y., Lu, L. D., Yang, X. J., Wang, X., Song, H. B., (2005), Synthesis, crystal structure and spectral characterization of the complex [Zn(tren)(SSA)]. Wuji Huaxue Xuebao, 21(4), 612-616.
  • Marinescu, M., (2017), 2-Aminopyridine – a classic and trendy pharmacophore. International Journal of Pharma and Bio Sciences, 8(2), 338-335.
  • Nakamoto, K., Infrared and raman spectra of inorganic and coordination compounds, 5th ed Wiley-Interscience, New York, 1997.
  • Rajagopalan, K. V., Kalyanaraman, R., Sundaresan, M., (1988), Thermal decompositions of sulfosalicylates of magnesium(II), calcium(II) and zinc(II). Journal of Thermal Analysis and Calorimetry, 34(1), 329-334.
  • Randjelović, P., Veljković, S., Stojiljković, N., Sokolović, D., Ilić, I., Laketić, D., Randjelović, D., Randjelović, N., (2015), The beneficial biological properties of salicylic acid. Acta Facultatis Medicae Naissensis, 32, 259-265.
  • Sharma, G., Tandon, J. P., (1970), Potentiometric studies on stepwise mixed ligand complex formation copper(II), nickel(II), or zinc(II)-nitrilotriacetic acid-hydroxy acid. Journal of Inorganic and Nuclear Chemistry, 32(4), 1273-1278.
  • Song, J. H., Kim, D. W., Kang, D. W., Lee, W. R., Hong, C.S., (2019), Humidity-triggered single-crystal-to-single-crystal structural transformations in a Zn(II) coordination polymer displaying unusual activation energy change in proton conductivity. Chemical Communications, 55(65), 9713-9716.
  • Tunca, E., Bülbül, M., İlkimen, H., Canlıdinç, R.S., Yenikaya, C., (2020), Investigation of the effects of the proton transfer salts of 2-aminopyridine derivatives with 5-sulfosalicylic acid and their Cu(II) complexes on cancer-related carbonic anhydrases: CA IX and CA XII. Chemical Papers, 74, 2365-2374.
  • Xu, T. Y., Wang, H., Li, J. M., Zhao, Y. L., Han, Y. H., Wang, X. L., He, K. H., Wang, A. R., Shi, Z. F., (2019), A water-stable luminescent Zn(II) coordination polymer based on 5-sulfosalicylic acid and 1,4-bis(1Himidazol-1-yl)benzene for highly sensitive and selective sensing of Fe ion. Inorganica Chimica Acta, 493, 72-80.
  • Xu, T. Y., Nie, H. J., Li, J. M., Shi, Z. F., (2020), Highly selective sensing of Fe3+/Hg2+ and proton conduction using two fluorescent Zn(II) coordination polymers. Dalton Transactions, 49(32), 11129-11141.
  • Yang, Y., Du, P., Ma, J. F., Kan, W. Q., Liu, B., Yang, J., (2011), Series of metal-organic frameworks based on different salicylic derivatives and 1,1'-(1,4-butanediyl)bis(imidazole) ligand: syntheses, structures, and luminescent properties. Crystal Growth Design, 11(12), 5540-5553.
  • Zhang, K. L., Yang, B., Ng, S. W., (2009), Diaquabis(1,10-phenanthroline-κ2N,N')zinc(II) 2-hydroxy-5-sulfonatobenzoate tetrahydrate. Acta Crystallographica, E65(2), m239-m240.
  • Zordok, W. A., Sadeek, S. A., El-Farargy, A. F., (2017), Synthesis, characterization, DFT modeling and biological studies of new Co(II), Ni(II) and Cu(II) 4,6-bis(4-chlorophenyl)-2-amino-1,2-dihydropyridine-3-carbinitrile complexes. Journal of the Iranian Chemical Society, 14(12), 2529-2547.
  • Zotkin, I. I., Kuznetsova, N. V., Kabanova, L., (2013), Zinc or copper(2+) salts used as biocides in polymer materials. Russian Federation, RU2497857 C1 2013-11-10.

Synthesis and Characterization of Zn(II) Complexes of 2-Amino-6-substituepyridine Derivatives and 5-Sulfosalicylic Acid

Yıl 2024, Cilt: 50 Sayı: 2, 43 - 48, 01.10.2024

Halil İlkimen , Cengiz Yenikaya , Zeynep Alkan Alkaya

https://doi.org/10.35238/sufefd.1454696

Öz

This study, four new Zn(II) complexes {(HX)2[Zn(Hssal)2(H2O)2], (H3ssal: 5-sulfosalicylic acid, X = 2-amino-6-methylpyridine (1) for 5, 2-amino-3-ethyl-6-methylpyridine (2) for 6, 2-amino-3-nitro-6-methylpyridine (3) for 7, and [Zn(Hssal)(X)2(H2O)2], X = 2-amino-3-nitro-6-chloropyridine (4) for 8} were synthesized. The structures of Zn(II) complexes (5-8) were characterized by elemental analysis, AAS, FT-IR, molar conductivity and magnetic susceptibility analyses. The results of IR and conductivity analyses, it was observed that 5-7 metal complexes were ionic, while 8 metal complexes were non-ionic. AAS and elemental analysis tests also support these results. In magnetic susceptibility studies, it was observed that Zn(II) (d10) metal complexes did not carry unpaired electrons as expected. The results of the spectroscopic analysis of complexes 5-8 have an octahedral structure.

Anahtar Kelimeler

5-Sulfosalicylic acid 2-Aminopyridine Zn(II) complex Octahedral structure

Kaynakça

  • Banowski, B., Kropf, C., (2015), Cosmetic antiperspirants with aromatic sulphonic acids. Germany, DE102013220789 A1 2015-04-16a.
  • Banowski, B., Kropf, C., (2015), Cosmetic antiperspirants with aromatic sulphonic acids. World Intellectual Property Organization, WO2015055198 A1 2015-04-23b.
  • Buyukkidan, N., Yenikaya, C., Ilkimen, H., Karahan, C., Darcan, C., Şahin, E., (2013), Synthesis, characterization and antimicrobial activity of a novel proton salt and its Cu(II) complex. Russian Journal of Coordination Chemistry, 39(1), 96-103.
  • Chen, Z. F., Shi, S. M., Hu, R. X., Zhang, M., Liang, H., Zhou, Z. Y., (2003), Synthesis, crystal structure, fluorescence property and antibacterial activity of two unprecedented one-dimensional chain metalorganic coordination polymers: Zn(H-SSA)(Phen)(H2O)2 and Cu(H-SSA)(Phen)(H2O)2. Chinese Journal of Chemistry, 21(8), 1059-1065.
  • Cook, D., (1961), Vibrational spectra of pyridinium salts. Canadian Journal of Chemistry, 39(10), 2009-2024.
  • Du, Z. X., Li, J. X., Wang, L. Y., (2009), Syntheses, crystal structures and fluorescent properties of two 4,4'-dipyridylsulfide based zinc(II) and cadmium(II) helical complexes. Journal of Coordination Chemistry, 62(15), 2411-2420.
  • Duan, X., Li, D., Lin, Y., Zhang, L., Tuo, Z., (2006), Method for preparing layered double hydroxides-sulfosalicylic acid having supramol İntercalating structure and its application. China, CN1861702 A 2006-11-15.
  • Fan, S. R., Zhu, L. G., Xiao, H. P., (2005), catena-Poly[[cis-diaqua(2,2'-bipyridine)zinc(II)]-μ-5-sulfonatosalicylato]. Acta Crystallographica, E61(5), m804-m806.
  • Geary, W. J., (1971), The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coordination Chemistry Reviews, 7, 81-122.
  • Han, Q., Wang, X. C., Li, X. Y., Yao, G. X., Yan, Y. S., (2009), Aqua(2-hydroxy-5-sulfonatobenzoato-κO1)bis(2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene-κ2N7,N8)zinc(II). Acta Crystallographica, E65(11), m1282-m1283.
  • Hecht, E., (2004), catena-Poly[[tetraaquazinc(II)]-μ-5-sulfosalicylato-κ2O:O'] Acta Crystallographica, E60(9), m1286-m1288.
  • Heleno, S. A., Martins, A., Queiroz, M. J. R. P, Ferreira, I. C. F. R., (2015), Bioactivity of phenolic acids: metabolites versus parent compounds: a review. Food Chemistry, 173, 501-513.
  • Ilkimen, H., İlkimen, B., Yenikaya, C., (2022), Metal complexes of 5-sulfosalicylic acid. New developments in science and mathematics, Bölüm 2.3, ss 221-234, Hiperyayın Evi.
  • Ivanova, B., Spiteller, M., (2017), On the nature of the coordination bonding of metal-organics for ions with the d10 electronic configuration - Experimental and theoretical analyses. Polyhedron, 137, 256-264.
  • Khadikar, P. V., Joshi, S., Kashkhedikar, S. G., Heda, B. D., (1984), Metal-complexes of 5-sulfosalicylic acid and their antimicrobial activity. Indian Journal of Pharmaceutical Sciences, 46(6), 209-211.
  • Koksharova, T., Slyvka, Y., Savchenko, O., Mandzii, T., Smola, S., (2023), 5-Sulfosalicylato Cu(II), Zn(II) and Ni(II) coordination compounds with benzohydrazide: Synthesis, structure and luminescent properties. Journal of Molecular Structure, 1271, 133980.
  • Lamshoeft, M., Storp, J., Ivanova, B., Spiteller, M., (2011), Gas-phase CT-stabilized Ag(I) and Zn(II) metal-organic complexes - Experimental versus theoretical study. Polyhedron, 30(15), 2564-2573.
  • Ma, J. F., Yang, J., Liu, J. F., (2003), Hexaaquazinc(II) 3-carboxy-4-hydroxybenzenesulfonate tetrahydrate. Acta Crystallographica, E59(7), m487-m488.
  • Ma, W. X., Qian, B. H., Gao, J., Xu, X. Y., Lu, L. D., Yang, X. J., Wang, X., Song, H. B., (2005), Synthesis, crystal structure and spectral characterization of the complex [Zn(tren)(SSA)]. Wuji Huaxue Xuebao, 21(4), 612-616.
  • Marinescu, M., (2017), 2-Aminopyridine – a classic and trendy pharmacophore. International Journal of Pharma and Bio Sciences, 8(2), 338-335.
  • Nakamoto, K., Infrared and raman spectra of inorganic and coordination compounds, 5th ed Wiley-Interscience, New York, 1997.
  • Rajagopalan, K. V., Kalyanaraman, R., Sundaresan, M., (1988), Thermal decompositions of sulfosalicylates of magnesium(II), calcium(II) and zinc(II). Journal of Thermal Analysis and Calorimetry, 34(1), 329-334.
  • Randjelović, P., Veljković, S., Stojiljković, N., Sokolović, D., Ilić, I., Laketić, D., Randjelović, D., Randjelović, N., (2015), The beneficial biological properties of salicylic acid. Acta Facultatis Medicae Naissensis, 32, 259-265.
  • Sharma, G., Tandon, J. P., (1970), Potentiometric studies on stepwise mixed ligand complex formation copper(II), nickel(II), or zinc(II)-nitrilotriacetic acid-hydroxy acid. Journal of Inorganic and Nuclear Chemistry, 32(4), 1273-1278.
  • Song, J. H., Kim, D. W., Kang, D. W., Lee, W. R., Hong, C.S., (2019), Humidity-triggered single-crystal-to-single-crystal structural transformations in a Zn(II) coordination polymer displaying unusual activation energy change in proton conductivity. Chemical Communications, 55(65), 9713-9716.
  • Tunca, E., Bülbül, M., İlkimen, H., Canlıdinç, R.S., Yenikaya, C., (2020), Investigation of the effects of the proton transfer salts of 2-aminopyridine derivatives with 5-sulfosalicylic acid and their Cu(II) complexes on cancer-related carbonic anhydrases: CA IX and CA XII. Chemical Papers, 74, 2365-2374.
  • Xu, T. Y., Wang, H., Li, J. M., Zhao, Y. L., Han, Y. H., Wang, X. L., He, K. H., Wang, A. R., Shi, Z. F., (2019), A water-stable luminescent Zn(II) coordination polymer based on 5-sulfosalicylic acid and 1,4-bis(1Himidazol-1-yl)benzene for highly sensitive and selective sensing of Fe ion. Inorganica Chimica Acta, 493, 72-80.
  • Xu, T. Y., Nie, H. J., Li, J. M., Shi, Z. F., (2020), Highly selective sensing of Fe3+/Hg2+ and proton conduction using two fluorescent Zn(II) coordination polymers. Dalton Transactions, 49(32), 11129-11141.
  • Yang, Y., Du, P., Ma, J. F., Kan, W. Q., Liu, B., Yang, J., (2011), Series of metal-organic frameworks based on different salicylic derivatives and 1,1'-(1,4-butanediyl)bis(imidazole) ligand: syntheses, structures, and luminescent properties. Crystal Growth Design, 11(12), 5540-5553.
  • Zhang, K. L., Yang, B., Ng, S. W., (2009), Diaquabis(1,10-phenanthroline-κ2N,N')zinc(II) 2-hydroxy-5-sulfonatobenzoate tetrahydrate. Acta Crystallographica, E65(2), m239-m240.
  • Zordok, W. A., Sadeek, S. A., El-Farargy, A. F., (2017), Synthesis, characterization, DFT modeling and biological studies of new Co(II), Ni(II) and Cu(II) 4,6-bis(4-chlorophenyl)-2-amino-1,2-dihydropyridine-3-carbinitrile complexes. Journal of the Iranian Chemical Society, 14(12), 2529-2547.
  • Zotkin, I. I., Kuznetsova, N. V., Kabanova, L., (2013), Zinc or copper(2+) salts used as biocides in polymer materials. Russian Federation, RU2497857 C1 2013-11-10.
Toplam 32 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Geçiş Metal Kimyası
Bölüm Araştırma Makaleleri
Yazarlar

Halil İlkimen 0000-0003-1747-159X

Cengiz Yenikaya 0000-0002-5867-9146

Zeynep Alkan Alkaya 0000-0003-0934-4195

Erken Görünüm Tarihi 21 Eylül 2024
Yayımlanma Tarihi 1 Ekim 2024
Gönderilme Tarihi 18 Mart 2024
Kabul Tarihi 24 Haziran 2024
Yayımlandığı Sayı Yıl 2024 Cilt: 50 Sayı: 2

Kaynak Göster

APA İlkimen, H., Yenikaya, C., & Alkan Alkaya, Z. (2024). 2-Amino-6-sübstitüepiridin Türevleri ile 5-Sülfosalisilik Asitin Zn(II) Komplekslerinin Sentezi ve Karakterizasyonu. Selcuk University Journal of Science Faculty, 50(2), 43-48. https://doi.org/10.35238/sufefd.1454696
AMA İlkimen H, Yenikaya C, Alkan Alkaya Z. 2-Amino-6-sübstitüepiridin Türevleri ile 5-Sülfosalisilik Asitin Zn(II) Komplekslerinin Sentezi ve Karakterizasyonu. Selcuk University Journal of Science Faculty. Ekim 2024;50(2):43-48. doi:10.35238/sufefd.1454696
Chicago İlkimen, Halil, Cengiz Yenikaya, ve Zeynep Alkan Alkaya. “2-Amino-6-sübstitüepiridin Türevleri Ile 5-Sülfosalisilik Asitin Zn(II) Komplekslerinin Sentezi Ve Karakterizasyonu”. Selcuk University Journal of Science Faculty 50, sy. 2 (Ekim 2024): 43-48. https://doi.org/10.35238/sufefd.1454696.
EndNote İlkimen H, Yenikaya C, Alkan Alkaya Z (01 Ekim 2024) 2-Amino-6-sübstitüepiridin Türevleri ile 5-Sülfosalisilik Asitin Zn(II) Komplekslerinin Sentezi ve Karakterizasyonu. Selcuk University Journal of Science Faculty 50 2 43–48.
IEEE H. İlkimen, C. Yenikaya, ve Z. Alkan Alkaya, “2-Amino-6-sübstitüepiridin Türevleri ile 5-Sülfosalisilik Asitin Zn(II) Komplekslerinin Sentezi ve Karakterizasyonu”, Selcuk University Journal of Science Faculty, c. 50, sy. 2, ss. 43–48, 2024, doi: 10.35238/sufefd.1454696.
ISNAD İlkimen, Halil vd. “2-Amino-6-sübstitüepiridin Türevleri Ile 5-Sülfosalisilik Asitin Zn(II) Komplekslerinin Sentezi Ve Karakterizasyonu”. Selcuk University Journal of Science Faculty 50/2 (Ekim 2024), 43-48. https://doi.org/10.35238/sufefd.1454696.
JAMA İlkimen H, Yenikaya C, Alkan Alkaya Z. 2-Amino-6-sübstitüepiridin Türevleri ile 5-Sülfosalisilik Asitin Zn(II) Komplekslerinin Sentezi ve Karakterizasyonu. Selcuk University Journal of Science Faculty. 2024;50:43–48.
MLA İlkimen, Halil vd. “2-Amino-6-sübstitüepiridin Türevleri Ile 5-Sülfosalisilik Asitin Zn(II) Komplekslerinin Sentezi Ve Karakterizasyonu”. Selcuk University Journal of Science Faculty, c. 50, sy. 2, 2024, ss. 43-48, doi:10.35238/sufefd.1454696.
Vancouver İlkimen H, Yenikaya C, Alkan Alkaya Z. 2-Amino-6-sübstitüepiridin Türevleri ile 5-Sülfosalisilik Asitin Zn(II) Komplekslerinin Sentezi ve Karakterizasyonu. Selcuk University Journal of Science Faculty. 2024;50(2):43-8.
 Kapak Resmi İndir

Journal Owner: On behalf of Selçuk University Faculty of Science, Rector Prof. Dr. Hüseyin YILMAZ
Selcuk University Journal of Science Faculty accepts articles in Turkish and English with original results in basic sciences and other applied sciences. The journal may also include compilations containing current innovations.

It was first published in 1981 as "S.Ü. Fen-Edebiyat Fakültesi Dergisi" and was published under this name until 1984 (Number 1-4).
In 1984, its name was changed to "S.Ü. Fen-Edeb. Fak. Fen Dergisi" and it was published under this name as of the 5th issue.
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