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Bazı benzotiyoat türevlerinin sentezi, karakterizasyonu ve Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ iyonları ile ekstraksiyonlarının incelenmesi

Yıl 2022, Cilt: 24 Sayı: 1, 212 - 221, 05.01.2022
https://doi.org/10.25092/baunfbed.937720

Öz

Tiyol bileşiklerinin biyolojik öneme sahip olması son yıllarda bu bileşiklere olan ilgiyi artırmıştır. Tiyol bileşiklerinden elde edilen tiyoester, tiyoeter ve disülfid bileşikleri altın, gümüş, demir, cıva, kadmiyum, çinko gibi metalleri seçimli olarak bağlamaktadır. Bu sebeple elde edilen komplekslerin lüminesans, güneş pilleri ve panelleri, katalizör sistemleri, adsorbanlar, fotovoltaik hücreler, vb. birçok kullanım alanı bulunmaktadır. Bu çalışmada disülfid bağı içeren orto/meta/para-kloro-aromatik benzotioat türevleri (L1-L3) tiyoesterleşme reaksiyonuyla sentezlenmiştir. Karakterizasyonları, FT-IR, 1H-NMR, 13C-NMR ve LC-MS/MS teknikleriyle gerçekleştirilmiştir. Sentezlenen benzotioat türevleri ile Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ iyonlarının kompleksleşmeleri sıvı-sıvı iyon çiftleri ekstraksiyonu (diklorometan:su (1:1)) ile belirlenmiştir. Ekstraksiyon denge sabitleri Kext, KD, %Ext, ΔGoext değerleri belirlenmiştir. L1 ve L2 ligandı en çok Cr3+ iyonunu (sırasıyla %Ext: %47.84 ve %78.96), L3 ligandı en fazla Fe3+ iyonunu (%Ext: %98.95) ekstrakte etmiştir.

Teşekkür

Bu çalışmanın bir kısmı Balıkesir Üniversitesi Fen Edebiyat Fakültesi Kimya Bölümü Organik Kimya Laboratuvarında gerçekleştirilmiştir. Laboratuvar yöneticisi Prof. Dr. Baki ÇİÇEK’e teşekkür ederim.

Kaynakça

  • Capozzi, G. et al., The chemistry of thiol group: Part 1, 1, John Wiley & Sons Ltd., London, (1974).
  • Voss, J., 2.5-Synthesis of Thioesters and Thiolactones in Trost, B. M. ve Fleming, I., Comprehensive Organic Synthesis, Pergamon Press, 435–460, Oxford, (1991).
  • Witt, D., Klajn, R., Barski, P. ve Grzybowski, B., Applications, properties and synthesis of ω-functionalized n-alkanethiols and disulfides - the building blocks of self-assembled monolayers, Current Organic Chemistry, 8, 1763–1797, (2005).
  • Rayner, C. M., Synthesis of thiols, sulfides, sulfoxides and sulfones, Contemporary Organic Synthesis, 2, 409–440, (1995).
  • Paradisi, C., 2.1-Arene substitution via nucleophilic addition to electron deficient arenes in Trost, B. M. ve Fleming, I. Comprehensive Organic Synthesis, Pergamon Press, 423–450, Oxford, (1991).
  • Çiçek, B. ve Çalışır, Ü., The Investigation of Complexation Properties and Hard-Soft Acid-Base Relationship Between Thiacrown Ethers and Metal Ions, Letters in Organic Chemistry, 13, 572–577, (2016).
  • Çalışır, Ü. ve Çiçek, B., Taç eterlerin metal iyonları ile kompleksleşmesinin kondüktometriye Job’s Plot yönteminin uygulanması ile belirlenmesi, Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 21, 840–854, (2019).
  • Akkemik, E., Cicek, B., Camadan, Y., Calisir, U. ve Onbasioglu, Z., The determination of the carbonic anhydrases activators in vitro effect of mixed donor crown ethers, Journal of Biochemical and Molecular Toxicology, 32, 3, e22032, (2018).
  • Akkemik, E., Çalışır, Ü. ve Çiçek, B., İnsan karbonik anhidraz I,II izoenzim aktiviteleri üzerine bazı tiyocrown eterlerin etkisi, Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 19, 192–199, (2017).
  • Kiso, Y. ve Yajima, H., 2-Amide formation, deprotection, and disulfide formation in peptide synthesis in Gutte, B., Peptides, Academic Press, 39–91, (1995).
  • Jordan, A. ve Reichard, P., Ribonucleotide reductases, Annual Review of Biochemistry, 67, 71–98, (1998).
  • Malle, E., Furtmüller, P. G., Sattler, W. ve Obinger, C., Myeloperoxidase: a target for new drug development?, British Journal of Pharmacology, 152, 838–854, (2007).
  • Janssen, M. J., Thiolo, thiono and dithio acids and esters in Patai, S., Carboxylic Acids and Esters, John Wiley ve Sons Ltd., 705–764, London, (1969).
  • Fujiwara, S. ve Kambe, N., Thio-, Seleno-, and Telluro-Carboxylic Acid Esters in Kato, S., Chalcogenocarboxylic Acid Derivatives, Springer, 87–140 Berlin Heidelberg, (2005).
  • Baddiley, J., Thaın, E. M., Novellı, G. D. ve Lipmann, F., Structure of Coenzyme A, Nature, 171, 76, (1953).
  • Keating, T. A. ve Walsh, C. T., Initiation, elongation, and termination strategies in polyketide and polypeptide antibiotic biosynthesis, Current Opinion in Chemical Biology, 3, 598–606, (1999).
  • Khosla, C., Tang, Y., Chen, A. Y., Schnarr, N. A. ve Cane, D. E., Structure and Mechanism of the 6-Deoxyerythronolide B Synthase, Annual Review of Biochemistry, 76, 195–221, (2007).
  • Duarte, A. et al., Ultrasound promoted synthesis of thioesters from 2-mercaptobenzoxa(thia)zoles, Ultrasonics Sonochemistry, 17, 281–283, (2010).
  • Abenante, L. et al., Ultrasound-enhanced Ag-catalyzed decarboxylative coupling between α-keto acids and disulfides for the synthesis of thioesters, Ultrasonics Sonochemistry, 49, 41–46, (2018).
  • Lucas, C. R. ve Liu, S., Macrocylic thioether-esters and thioether-thioesters and their palladium, platinum and silver complexes, Inorganica Chimica Acta, 230, 133–138, (1995).
  • Grant, G. J. et al., Transition metal complexes with macrocyclic oxathiaethers, Inorganica Chimica Acta, 300–302, 250–263, (2000).
  • Calisir, U. ve Çiçek, B., Comparison of classic and microwave-assisted synthesis of benzo-thio crown ethers, and investigation of their ion pair extractions, Journal Molecular Structure, 1148, 505–511, (2017).
  • Çiçek, B. ve Onbaşıoğlu, Z., Synthesis and characterization of 1,3,4-thiadiazole-2,5-dithio crown ethers, Heterocyclic Communications, 22, 329–332, (2016).
  • Çiçek, B. ve Yıldız, A., Synthesis, Metal Ion Complexation and Computational Studies of Thio Oxocrown Ethers, Molecules, 16, 8670–8683, (2011).
  • Erk, C., Cakir, U. ve Cicek, B., Estimation of Li+, K+ and Ca2+ complexation with 12 crown-4, 15 crown-5 and 18 crown-6 using a Na+ISE in dioxane-water, part IV - Cation equilibrium constants of macrocyclic ethers with ion selective electrodes, Mikrochimica Acta, 132, 79–82, (1999).
  • Ahmad, S. ve Iqbal, J., Cobalt(II) chloride catalysed coupling of thiols and anhydrides: A new and efficient synthesis of thiol esters, Tetrahedron Letters, 27, 3791–3794, (1986).
  • Reißig, H.-U. ve Scherer, B., A simple synthesis of thiol esters from copper-I-mercaptides and acyl chlorides, Tetrahedron Letters, 21, 4259–4262, (1980).
  • Bandgar, S. B., Bandgar, B. P., Korbad, B. L. ve Sawant, S. S., Dess–Martin periodinane mediated synthesis of thioesters from aldehydes, Tetrahedron Letters, 48, 1287–1290, (2007).
  • Yan, F., Zhu, Q., Li, Q.-L., Zhang, R.-F. ve Ma, C.-L., Triorganotin coordination polymers based on three dicarboxylate ligands containing flexible SS bonds: synthesis, structures and in vitro anti-tumor activity, Journal Organometalic Chemistry, 880, 156–162, (2019).
  • Sepehrikia, S., Arefi, D. ve Shams, A., Fluorescence quantum yield of the two novel macrocyclic lactams, Russian Journal of Physical Chemistry A, 88, 2462–2465, (2014).
  • Bukonjić, A. M. et al., Antibacterial, antibiofilm and antioxidant screening of copper(II)-complexes with some S-alkyl derivatives of thiosalicylic acid. Crystal structure of the binuclear copper(II)-complex with S-propyl derivative of thiosalicylic acid, Journal of Molecular Structure, 1128, 330–337, (2017).
  • Çakir, Ü., Çiçek, B., Yildiz, Y. K. ve Alkan, M., Solvent effect upon ion-pair extraction of different sodium dyes using some crown ethers, Journal of Inclusion Phenomena Macrocyclic Chemistry, 34, 153–165, (1999).
  • Çakir, Ü. ve Çiçek, B., Extraction-ability and -selectivity of tetra-aza-crown ethers for transition metal cations, Transition Metal Chemistry, 29, 263-268, (2004).
  • Çiçek, B., Çakir, Ü. ve Azizoglu, A., The associations of macrocyclic ethers with cations in 1,4-dioxane/ water mixtures; Potentiometric Na+ and K+ binding measurements and computational study, Journal of Inclusion Phenomena Macrocyclic Chemistry, 72, 121–125, (2012).
  • Eshghi, H., Seyedi, S. M. ve Sandarooss, R., Synthesis of novel disulfide-bridged dilactam crown ethers, Chinese Chemical. Letters, 18, 1439–1442, (2007).
  • Çiçek, B., The synthesis of coronands and studies of their complexation ability using potentiometric, conductometric and liquid-liquid extraction methods, Doktora Tezi, Balıkesir Üniversitesi, Fen Bilimleri Enstitüsü, Balıkesir, (2002).
  • Hassine, A. et al., Natural phosphate-supported palladium: A highly efficient and recyclable catalyst for the Suzuki-Miyaura Coupling under microwave irradiation, Current Organic Chemistry, 18, 3141–3148, (2014).
  • Çalışır, Ü. ve Çiçek, B., Synthesis of thiol-glycol-functionalized carbon nanotubes and characterization with FTIR, TEM, TGA, and NMR technics, Chemical Papers, 74, 3293–3302, (2020).

Synthesis and characterization of some benzothioate derivatives and investigation of extractions with Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ ions

Yıl 2022, Cilt: 24 Sayı: 1, 212 - 221, 05.01.2022
https://doi.org/10.25092/baunfbed.937720

Öz

The biological importance of thiol compounds has increased the interest in these compounds in recent years. Thioester, thioether and disulfide compounds obtained from thiol compounds selectively bind metals such as gold, silver, iron, mercury, cadmium, zinc. Therefore, the complexes obtained have many usage areas such as luminescence, solar cells and panels, catalyst systems, adsorbents, photovoltaic cells, etc. In this study, ortho/meta/para-chloro-aromatic benzothioate derivatives (L1-L3) containing disulfide bonds were synthesized by thioesterification reaction. Characterizations were carried out by FT-IR, 1H-NMR, 13C-NMR and LC-MS/MS techniques. The complexes of synthesized benzothioate derivatives and Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ ions were determined by liquid-liquid extraction (dichloromethane:water (1:1)). Extraction equilibrium constants Kext, KD, Ext%, ΔGoext values were determined. L1 and L2 ligand extracted the most Cr3+ ion (Ext%: 47.84% and 78.96%, respectively), and L3 ligand extracted the most Fe3+ ion (Ext%: 98.95%).

Kaynakça

  • Capozzi, G. et al., The chemistry of thiol group: Part 1, 1, John Wiley & Sons Ltd., London, (1974).
  • Voss, J., 2.5-Synthesis of Thioesters and Thiolactones in Trost, B. M. ve Fleming, I., Comprehensive Organic Synthesis, Pergamon Press, 435–460, Oxford, (1991).
  • Witt, D., Klajn, R., Barski, P. ve Grzybowski, B., Applications, properties and synthesis of ω-functionalized n-alkanethiols and disulfides - the building blocks of self-assembled monolayers, Current Organic Chemistry, 8, 1763–1797, (2005).
  • Rayner, C. M., Synthesis of thiols, sulfides, sulfoxides and sulfones, Contemporary Organic Synthesis, 2, 409–440, (1995).
  • Paradisi, C., 2.1-Arene substitution via nucleophilic addition to electron deficient arenes in Trost, B. M. ve Fleming, I. Comprehensive Organic Synthesis, Pergamon Press, 423–450, Oxford, (1991).
  • Çiçek, B. ve Çalışır, Ü., The Investigation of Complexation Properties and Hard-Soft Acid-Base Relationship Between Thiacrown Ethers and Metal Ions, Letters in Organic Chemistry, 13, 572–577, (2016).
  • Çalışır, Ü. ve Çiçek, B., Taç eterlerin metal iyonları ile kompleksleşmesinin kondüktometriye Job’s Plot yönteminin uygulanması ile belirlenmesi, Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 21, 840–854, (2019).
  • Akkemik, E., Cicek, B., Camadan, Y., Calisir, U. ve Onbasioglu, Z., The determination of the carbonic anhydrases activators in vitro effect of mixed donor crown ethers, Journal of Biochemical and Molecular Toxicology, 32, 3, e22032, (2018).
  • Akkemik, E., Çalışır, Ü. ve Çiçek, B., İnsan karbonik anhidraz I,II izoenzim aktiviteleri üzerine bazı tiyocrown eterlerin etkisi, Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 19, 192–199, (2017).
  • Kiso, Y. ve Yajima, H., 2-Amide formation, deprotection, and disulfide formation in peptide synthesis in Gutte, B., Peptides, Academic Press, 39–91, (1995).
  • Jordan, A. ve Reichard, P., Ribonucleotide reductases, Annual Review of Biochemistry, 67, 71–98, (1998).
  • Malle, E., Furtmüller, P. G., Sattler, W. ve Obinger, C., Myeloperoxidase: a target for new drug development?, British Journal of Pharmacology, 152, 838–854, (2007).
  • Janssen, M. J., Thiolo, thiono and dithio acids and esters in Patai, S., Carboxylic Acids and Esters, John Wiley ve Sons Ltd., 705–764, London, (1969).
  • Fujiwara, S. ve Kambe, N., Thio-, Seleno-, and Telluro-Carboxylic Acid Esters in Kato, S., Chalcogenocarboxylic Acid Derivatives, Springer, 87–140 Berlin Heidelberg, (2005).
  • Baddiley, J., Thaın, E. M., Novellı, G. D. ve Lipmann, F., Structure of Coenzyme A, Nature, 171, 76, (1953).
  • Keating, T. A. ve Walsh, C. T., Initiation, elongation, and termination strategies in polyketide and polypeptide antibiotic biosynthesis, Current Opinion in Chemical Biology, 3, 598–606, (1999).
  • Khosla, C., Tang, Y., Chen, A. Y., Schnarr, N. A. ve Cane, D. E., Structure and Mechanism of the 6-Deoxyerythronolide B Synthase, Annual Review of Biochemistry, 76, 195–221, (2007).
  • Duarte, A. et al., Ultrasound promoted synthesis of thioesters from 2-mercaptobenzoxa(thia)zoles, Ultrasonics Sonochemistry, 17, 281–283, (2010).
  • Abenante, L. et al., Ultrasound-enhanced Ag-catalyzed decarboxylative coupling between α-keto acids and disulfides for the synthesis of thioesters, Ultrasonics Sonochemistry, 49, 41–46, (2018).
  • Lucas, C. R. ve Liu, S., Macrocylic thioether-esters and thioether-thioesters and their palladium, platinum and silver complexes, Inorganica Chimica Acta, 230, 133–138, (1995).
  • Grant, G. J. et al., Transition metal complexes with macrocyclic oxathiaethers, Inorganica Chimica Acta, 300–302, 250–263, (2000).
  • Calisir, U. ve Çiçek, B., Comparison of classic and microwave-assisted synthesis of benzo-thio crown ethers, and investigation of their ion pair extractions, Journal Molecular Structure, 1148, 505–511, (2017).
  • Çiçek, B. ve Onbaşıoğlu, Z., Synthesis and characterization of 1,3,4-thiadiazole-2,5-dithio crown ethers, Heterocyclic Communications, 22, 329–332, (2016).
  • Çiçek, B. ve Yıldız, A., Synthesis, Metal Ion Complexation and Computational Studies of Thio Oxocrown Ethers, Molecules, 16, 8670–8683, (2011).
  • Erk, C., Cakir, U. ve Cicek, B., Estimation of Li+, K+ and Ca2+ complexation with 12 crown-4, 15 crown-5 and 18 crown-6 using a Na+ISE in dioxane-water, part IV - Cation equilibrium constants of macrocyclic ethers with ion selective electrodes, Mikrochimica Acta, 132, 79–82, (1999).
  • Ahmad, S. ve Iqbal, J., Cobalt(II) chloride catalysed coupling of thiols and anhydrides: A new and efficient synthesis of thiol esters, Tetrahedron Letters, 27, 3791–3794, (1986).
  • Reißig, H.-U. ve Scherer, B., A simple synthesis of thiol esters from copper-I-mercaptides and acyl chlorides, Tetrahedron Letters, 21, 4259–4262, (1980).
  • Bandgar, S. B., Bandgar, B. P., Korbad, B. L. ve Sawant, S. S., Dess–Martin periodinane mediated synthesis of thioesters from aldehydes, Tetrahedron Letters, 48, 1287–1290, (2007).
  • Yan, F., Zhu, Q., Li, Q.-L., Zhang, R.-F. ve Ma, C.-L., Triorganotin coordination polymers based on three dicarboxylate ligands containing flexible SS bonds: synthesis, structures and in vitro anti-tumor activity, Journal Organometalic Chemistry, 880, 156–162, (2019).
  • Sepehrikia, S., Arefi, D. ve Shams, A., Fluorescence quantum yield of the two novel macrocyclic lactams, Russian Journal of Physical Chemistry A, 88, 2462–2465, (2014).
  • Bukonjić, A. M. et al., Antibacterial, antibiofilm and antioxidant screening of copper(II)-complexes with some S-alkyl derivatives of thiosalicylic acid. Crystal structure of the binuclear copper(II)-complex with S-propyl derivative of thiosalicylic acid, Journal of Molecular Structure, 1128, 330–337, (2017).
  • Çakir, Ü., Çiçek, B., Yildiz, Y. K. ve Alkan, M., Solvent effect upon ion-pair extraction of different sodium dyes using some crown ethers, Journal of Inclusion Phenomena Macrocyclic Chemistry, 34, 153–165, (1999).
  • Çakir, Ü. ve Çiçek, B., Extraction-ability and -selectivity of tetra-aza-crown ethers for transition metal cations, Transition Metal Chemistry, 29, 263-268, (2004).
  • Çiçek, B., Çakir, Ü. ve Azizoglu, A., The associations of macrocyclic ethers with cations in 1,4-dioxane/ water mixtures; Potentiometric Na+ and K+ binding measurements and computational study, Journal of Inclusion Phenomena Macrocyclic Chemistry, 72, 121–125, (2012).
  • Eshghi, H., Seyedi, S. M. ve Sandarooss, R., Synthesis of novel disulfide-bridged dilactam crown ethers, Chinese Chemical. Letters, 18, 1439–1442, (2007).
  • Çiçek, B., The synthesis of coronands and studies of their complexation ability using potentiometric, conductometric and liquid-liquid extraction methods, Doktora Tezi, Balıkesir Üniversitesi, Fen Bilimleri Enstitüsü, Balıkesir, (2002).
  • Hassine, A. et al., Natural phosphate-supported palladium: A highly efficient and recyclable catalyst for the Suzuki-Miyaura Coupling under microwave irradiation, Current Organic Chemistry, 18, 3141–3148, (2014).
  • Çalışır, Ü. ve Çiçek, B., Synthesis of thiol-glycol-functionalized carbon nanotubes and characterization with FTIR, TEM, TGA, and NMR technics, Chemical Papers, 74, 3293–3302, (2020).
Toplam 38 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Bölüm Araştırma Makalesi
Yazarlar

Ümit Çalışır 0000-0001-7699-2008

Yayımlanma Tarihi 5 Ocak 2022
Gönderilme Tarihi 15 Mayıs 2021
Yayımlandığı Sayı Yıl 2022 Cilt: 24 Sayı: 1

Kaynak Göster

APA Çalışır, Ü. (2022). Bazı benzotiyoat türevlerinin sentezi, karakterizasyonu ve Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ iyonları ile ekstraksiyonlarının incelenmesi. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 24(1), 212-221. https://doi.org/10.25092/baunfbed.937720
AMA Çalışır Ü. Bazı benzotiyoat türevlerinin sentezi, karakterizasyonu ve Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ iyonları ile ekstraksiyonlarının incelenmesi. BAUN Fen. Bil. Enst. Dergisi. Ocak 2022;24(1):212-221. doi:10.25092/baunfbed.937720
Chicago Çalışır, Ümit. “Bazı Benzotiyoat türevlerinin Sentezi, Karakterizasyonu Ve Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ Iyonları Ile ekstraksiyonlarının Incelenmesi”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 24, sy. 1 (Ocak 2022): 212-21. https://doi.org/10.25092/baunfbed.937720.
EndNote Çalışır Ü (01 Ocak 2022) Bazı benzotiyoat türevlerinin sentezi, karakterizasyonu ve Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ iyonları ile ekstraksiyonlarının incelenmesi. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 24 1 212–221.
IEEE Ü. Çalışır, “Bazı benzotiyoat türevlerinin sentezi, karakterizasyonu ve Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ iyonları ile ekstraksiyonlarının incelenmesi”, BAUN Fen. Bil. Enst. Dergisi, c. 24, sy. 1, ss. 212–221, 2022, doi: 10.25092/baunfbed.937720.
ISNAD Çalışır, Ümit. “Bazı Benzotiyoat türevlerinin Sentezi, Karakterizasyonu Ve Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ Iyonları Ile ekstraksiyonlarının Incelenmesi”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 24/1 (Ocak 2022), 212-221. https://doi.org/10.25092/baunfbed.937720.
JAMA Çalışır Ü. Bazı benzotiyoat türevlerinin sentezi, karakterizasyonu ve Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ iyonları ile ekstraksiyonlarının incelenmesi. BAUN Fen. Bil. Enst. Dergisi. 2022;24:212–221.
MLA Çalışır, Ümit. “Bazı Benzotiyoat türevlerinin Sentezi, Karakterizasyonu Ve Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ Iyonları Ile ekstraksiyonlarının Incelenmesi”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, c. 24, sy. 1, 2022, ss. 212-21, doi:10.25092/baunfbed.937720.
Vancouver Çalışır Ü. Bazı benzotiyoat türevlerinin sentezi, karakterizasyonu ve Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ iyonları ile ekstraksiyonlarının incelenmesi. BAUN Fen. Bil. Enst. Dergisi. 2022;24(1):212-21.