Araştırma Makalesi
Yıl 2023,
Cilt: 18 Sayı: 2, 181 - 194, 22.06.2023
Öz
In this study, two different azo dyes were synthesized from the reaction of 2-amino benzothiazole derivative amine and heterocyclic coupling compounds. The structures of the synthesized compounds were characterized such as by 1H-NMR and FT-IR spectroscopic methods. Four different possible tautomer structures are contemplated for each of the compounds. Considering the spectroscopic results analysis, the molecular structure of each tautomer was evaluated. UV-Vis. absorption properties of the obtained azo dyestuff compounds were studied using six different solvents. On the other hand, the electronic data of the spectroscopic and absorption properties of the tautomeric structures of the final products were examined theoretically at the B3LYP/6-311++G(2d,2p) theory level with the DFT approach. The experimental and theoretical results obtained in the study were compared with each other and the results were discussed.
Anahtar Kelimeler
Destekleyen Kurum
Kastamonu Üniversitesi BAP Koordinatörlüğü
Proje Numarası
KÜ-BAP01/2019-9
Teşekkür
The authors are grateful to the Scientific Research Projects Council of Kastamonu University
Kaynakça
- H. Zollinger, “Color chemistry: Syntheses, Properties and Application of Organic, Dyes and Pigments” 2nd ed. Weinheim: VCH; 1991.
- P. I. Gregory and K. Hunger, “Industrial Dyes: Chemistry, Properties and Applications”, Weinheim: Wiley-VCH, 2002,pp.543–585.
- R. J. H. Clark and R. E. Hester, “Advances In Materials Science Spectroscopy”. New York:John Wiley & Sons; 1991.
- M. Neamtu, A. Yediler, I. Siminiceanu, M. Macoveanu and A. Kettrup, “Decolorization of disperse red 354 azo dye in water by several oxidation processes - a comparative study,” Dyes and Pigments, 60 (1), 61-68, 2004.
- A. Akbari, J. C. Remigy and P. Aptel, “Treatment of textile dye effluent using a polyamide- based nanofiltration membrane,” Chemical Engineering and Processing, 41 (7), 601-609, 2002.
- J. Geng, T. Tao, S. J. Fu, W. You and W. Huang, “Structural investigations on four heterocyclic Disperse Red azo dyes having the same benzothiazole/azo/benzene skeleton,” Dyes and Pigments, 90 (1), 65-70, 2011.
- A. D. Towns, “Developments in azo disperse dyes derived from heterocyclic diazo components,” Dyes and Pigments, 42, 3–28, 1999.
- M. R. Maliyappa, J. Keshavayya, N. M. Mallikarjuna, P. M. Krishna, N. Shivakumara, T. Sandeep and M. A. Nazrulla, “Synthesis, characterization, pharmacological and computational studies of 4, 5, 6, 7-tetrahydro-1, 3-benzothiazole incorporated azo dyes,” Journal of Molecular Structure, 1179, 630-641, 2019.
- B. N. Ravi, J. Keshavayya and N. M. Mallikarjuna, “Synthesis, spectral characterization and pharmacological evaluation of Ni (II) complexes of 6-nitro-benzothiazole incorporated azo dyes,” Journal of Inorganic and Organometallic Polymers and Materials, 30 (9), 3781-3796, 2020.
- C. W. Ghanavatkar, V. R. Mishra, N. Sekar, E. Mathew, S. S. Thomas and I. H. Joe, “Benzothiazole pyrazole containing emissive azo dyes decorated with ESIPT core: linear and nonlinear optical properties, Z scan, optical limiting, laser damage threshold with comparative DFT studies,” Journal of Molecular Structure, 1203, 127401, 2020.
- S. Prakash, G. Somiya, N. Elavarasan, K. Subashini, S. Kanaga, R. Dhandapani and V. Sujatha, “Synthesis and characterization of novel bioactive azo compounds fused with benzothiazole and their versatile biological applications,” Journal of Molecular Structure, 1224, 129016, 2021.
- V. R. Mishra, C. W. Ghanavatkar, S. N. Mali, S. I. Qureshi, H. K. Chaudhari and N. Sekar, “Design, synthesis, antimicrobial activity and computational studies of novel azo linked substituted benzimidazole, benzoxazole and benzothiazole derivatives,” Computational biology and chemistry, 78, 330-337, 2019.
- A. S. Özen, P. Doruker & V. Aviyente, “Effect of cooperative hydrogen bonding in azo− hydrazone tautomerism of azo dyes,” The Journal of Physical Chemistry A, 111 (51), 13506-13514, 2007.
- M. R. Maliyappa, J. Keshavayya, M. Mahanthappa, Y. Shivaraj and K. V. Basavarajappa, “6-Substituted benzothiazole based dispersed azo dyes having pyrazole moiety: synthesis, characterization, electrochemical and DFT studies,” Journal of Molecular Structure, 1199, 126959, 2020.
- S. Kınalı, S. Demirci, Z. Çalışır, M. Kurt and A. Ataç, “DFT, FT-IR, FT-Raman and NMR studies of 4-(substituted phenylazo)-3, 5-diacetamido-1H-pyrazoles,” Journal of Molecular Structure, 993 (1-3), 254-258, 2011.
- C. W. Ghanavatkar, V. R. Mishra, S. N. Mali, H. K. Chaudhari and N. Sekar, “Synthesis, bioactivities, DFT and in-silico appraisal of azo clubbed benzothiazole derivatives,” Journal of Molecular Structure, 1192, 162-171, 2019.
- S. Harisha, J. Keshavayya, S. M. Prasanna and H. J. Hoskeri, “Synthesis, characterization, pharmacological evaluation and molecular docking studies of benzothiazole azo derivatives,” Journal of Molecular Structure, 1218, 128477, 2020.
- B. Manjunatha, Y. D. Bodke, O. Nagaraja, G. Nagaraju and M. A. Sridhar, “Coumarin-benzothiazole based azo dyes: synthesis, characterization, computational, photophysical and biological studies,” Journal of Molecular Structure, 1246, 131170, 2021.
- M. R. Maliyappa, J. Keshavayya, M. S. Sudhanva and I. Pushpavathi, “Heterocyclic azo dyes derived from 2-(6-chloro-1, 3-benzothiazol-2-yl)-5-methyl-2, 4-dihydro-3H-pyrazol-3-one having benzothiazole skeleton: synthesis, structural, computational and biological studies,” Journal of Molecular Structure, 1247, 131321, 2022.
- M. R. Maliyappa, J. Keshavayya, M. Mahanthappa, Y. Shivaraj, K.V. Basavarajappa, “6-Substituted benzothiazole based dispersed azo dyes having pyrazole moiety: Synthesis, characterization, electrochemical and DFT studies”, Journal of Molecular Structure, 1199, 126959, 2020.
- C. W. Ghanavatkar, V. R. Mishra, N. Sekar, E. Mathew, S. Sijo Thomas, I. H. Joe, “Benzothiazole pyrazole containing emissive azo dyes decorated with ESIPT core: Linear and nonlinear optical properties, Z scan, optical limiting, laser damage threshold with comparative DFT studies”, Journal of Molecular Structure, 1203, 127401, 2020.
- M. Gökalp, T. Tilki, Ç. Karabacak Atay, “Newly Synthesized Aminothiazole Based Disazo Dyes and Their Theoretical Calculations”, Polycyclic Aromatic Compounds, 1(23), 2023.
- S. Erişkin, N. Şener, S. Yavuz and İ. Şener, “Synthesis, characterization, and biological activities of 4-imino-3-arylazo-4H-pyrimido[2, 1-b][1, 3]benzothiazole-2-oles,” Medicinal Chemistry Research, 23 (8), 3733-3743, 2014.
- P. Hohenberg and W. Kohn, Phys. Rev., 1964, 136, 864-871.
- W. Kohn and L. J. Sham, Phys. Rev., 1965, 140, 1133-1138.
- M. J. Frisch, G. Trucks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, G. Scalmani, V. Barone, B. Mennucci and G. Petersson, Inc.: Wallingford, CT, 2009.
- R. F. Bader, Acc. Chem. Res., 1985, 18, 9-15.
- R. F. Bader, Chem. Rev., 1991, 91, 893-928.
- Tian Lu and Qinxue Chen, “Interaction Region Indicator: A Simple Real Space Function Clearly Revealing Both Chemical Bonds and Weak Interactions,” Chemistry—Methods, 1 (5), 231-239, 2021.
- T. Lu and F. Chen, J. Comput. Chem., 2012, 33, 580-592.
- M. R. Maliyappa, J. Keshavayya, R. A. Shoukat Ali and S. Harisha, “Synthesis, Characterization, Solvatochromic and Biological studies of novel Benzothiazole based azo dyes,” Journal of Chemical and Pharmaceutical Sciences, Special Issue 1 (10-15), 2018.
Benzotiyazolden Elde Edilen Bazı Azo Boyarmaddelerin Sentezi ve Yoğunluk Fonksiyonel Teorisi ile Analizi
Öz
Yapılan bu çalışmada, 2-amino benzotiyazol türevi amin bileşikleri ve heterosiklik kenetleme bileşiğinin reaksiyonundan iki farklı azo boyarmadde sentezlenmiştir. Sentezlenen bileşiklerin molekül yapıları, 1H-NMR ve FT-IR gibi spektroskopik yöntemlerle karakter analizine tabi tutulmuştur. Bileşiklerin her biri için muhtemel olan dört farklı tautomer yapı öngörülmüştür. Spektroskopik sonuç analizleri dikkate alınarak, herbir tautomer molekül yapısı değerlendirilmiştir. Elde edilen azo boyarmadde bileşiklerinin UV-Vis. absorpsiyon özellikleri altı farklı çözücü kullanılarak çalışılmıştır. Öte yandan elde edilen nihai ürünlerin tautomerik yapılarının spektroskopik ve absorpsiyon özelliklerinin elektronik verileri DFT yaklaşımıyla B3LYP/6-311++g(2d,2p) teori seviyesinde teorik olarak incelenmiştir. Çalışma sonucunda elde edilen deneysel ve teorik sonuçlar birbirleri ile karşılaştırılmış ve sonuçlar tartışılmıştır
Anahtar Kelimeler
Proje Numarası
KÜ-BAP01/2019-9
Kaynakça
- H. Zollinger, “Color chemistry: Syntheses, Properties and Application of Organic, Dyes and Pigments” 2nd ed. Weinheim: VCH; 1991.
- P. I. Gregory and K. Hunger, “Industrial Dyes: Chemistry, Properties and Applications”, Weinheim: Wiley-VCH, 2002,pp.543–585.
- R. J. H. Clark and R. E. Hester, “Advances In Materials Science Spectroscopy”. New York:John Wiley & Sons; 1991.
- M. Neamtu, A. Yediler, I. Siminiceanu, M. Macoveanu and A. Kettrup, “Decolorization of disperse red 354 azo dye in water by several oxidation processes - a comparative study,” Dyes and Pigments, 60 (1), 61-68, 2004.
- A. Akbari, J. C. Remigy and P. Aptel, “Treatment of textile dye effluent using a polyamide- based nanofiltration membrane,” Chemical Engineering and Processing, 41 (7), 601-609, 2002.
- J. Geng, T. Tao, S. J. Fu, W. You and W. Huang, “Structural investigations on four heterocyclic Disperse Red azo dyes having the same benzothiazole/azo/benzene skeleton,” Dyes and Pigments, 90 (1), 65-70, 2011.
- A. D. Towns, “Developments in azo disperse dyes derived from heterocyclic diazo components,” Dyes and Pigments, 42, 3–28, 1999.
- M. R. Maliyappa, J. Keshavayya, N. M. Mallikarjuna, P. M. Krishna, N. Shivakumara, T. Sandeep and M. A. Nazrulla, “Synthesis, characterization, pharmacological and computational studies of 4, 5, 6, 7-tetrahydro-1, 3-benzothiazole incorporated azo dyes,” Journal of Molecular Structure, 1179, 630-641, 2019.
- B. N. Ravi, J. Keshavayya and N. M. Mallikarjuna, “Synthesis, spectral characterization and pharmacological evaluation of Ni (II) complexes of 6-nitro-benzothiazole incorporated azo dyes,” Journal of Inorganic and Organometallic Polymers and Materials, 30 (9), 3781-3796, 2020.
- C. W. Ghanavatkar, V. R. Mishra, N. Sekar, E. Mathew, S. S. Thomas and I. H. Joe, “Benzothiazole pyrazole containing emissive azo dyes decorated with ESIPT core: linear and nonlinear optical properties, Z scan, optical limiting, laser damage threshold with comparative DFT studies,” Journal of Molecular Structure, 1203, 127401, 2020.
- S. Prakash, G. Somiya, N. Elavarasan, K. Subashini, S. Kanaga, R. Dhandapani and V. Sujatha, “Synthesis and characterization of novel bioactive azo compounds fused with benzothiazole and their versatile biological applications,” Journal of Molecular Structure, 1224, 129016, 2021.
- V. R. Mishra, C. W. Ghanavatkar, S. N. Mali, S. I. Qureshi, H. K. Chaudhari and N. Sekar, “Design, synthesis, antimicrobial activity and computational studies of novel azo linked substituted benzimidazole, benzoxazole and benzothiazole derivatives,” Computational biology and chemistry, 78, 330-337, 2019.
- A. S. Özen, P. Doruker & V. Aviyente, “Effect of cooperative hydrogen bonding in azo− hydrazone tautomerism of azo dyes,” The Journal of Physical Chemistry A, 111 (51), 13506-13514, 2007.
- M. R. Maliyappa, J. Keshavayya, M. Mahanthappa, Y. Shivaraj and K. V. Basavarajappa, “6-Substituted benzothiazole based dispersed azo dyes having pyrazole moiety: synthesis, characterization, electrochemical and DFT studies,” Journal of Molecular Structure, 1199, 126959, 2020.
- S. Kınalı, S. Demirci, Z. Çalışır, M. Kurt and A. Ataç, “DFT, FT-IR, FT-Raman and NMR studies of 4-(substituted phenylazo)-3, 5-diacetamido-1H-pyrazoles,” Journal of Molecular Structure, 993 (1-3), 254-258, 2011.
- C. W. Ghanavatkar, V. R. Mishra, S. N. Mali, H. K. Chaudhari and N. Sekar, “Synthesis, bioactivities, DFT and in-silico appraisal of azo clubbed benzothiazole derivatives,” Journal of Molecular Structure, 1192, 162-171, 2019.
- S. Harisha, J. Keshavayya, S. M. Prasanna and H. J. Hoskeri, “Synthesis, characterization, pharmacological evaluation and molecular docking studies of benzothiazole azo derivatives,” Journal of Molecular Structure, 1218, 128477, 2020.
- B. Manjunatha, Y. D. Bodke, O. Nagaraja, G. Nagaraju and M. A. Sridhar, “Coumarin-benzothiazole based azo dyes: synthesis, characterization, computational, photophysical and biological studies,” Journal of Molecular Structure, 1246, 131170, 2021.
- M. R. Maliyappa, J. Keshavayya, M. S. Sudhanva and I. Pushpavathi, “Heterocyclic azo dyes derived from 2-(6-chloro-1, 3-benzothiazol-2-yl)-5-methyl-2, 4-dihydro-3H-pyrazol-3-one having benzothiazole skeleton: synthesis, structural, computational and biological studies,” Journal of Molecular Structure, 1247, 131321, 2022.
- M. R. Maliyappa, J. Keshavayya, M. Mahanthappa, Y. Shivaraj, K.V. Basavarajappa, “6-Substituted benzothiazole based dispersed azo dyes having pyrazole moiety: Synthesis, characterization, electrochemical and DFT studies”, Journal of Molecular Structure, 1199, 126959, 2020.
- C. W. Ghanavatkar, V. R. Mishra, N. Sekar, E. Mathew, S. Sijo Thomas, I. H. Joe, “Benzothiazole pyrazole containing emissive azo dyes decorated with ESIPT core: Linear and nonlinear optical properties, Z scan, optical limiting, laser damage threshold with comparative DFT studies”, Journal of Molecular Structure, 1203, 127401, 2020.
- M. Gökalp, T. Tilki, Ç. Karabacak Atay, “Newly Synthesized Aminothiazole Based Disazo Dyes and Their Theoretical Calculations”, Polycyclic Aromatic Compounds, 1(23), 2023.
- S. Erişkin, N. Şener, S. Yavuz and İ. Şener, “Synthesis, characterization, and biological activities of 4-imino-3-arylazo-4H-pyrimido[2, 1-b][1, 3]benzothiazole-2-oles,” Medicinal Chemistry Research, 23 (8), 3733-3743, 2014.
- P. Hohenberg and W. Kohn, Phys. Rev., 1964, 136, 864-871.
- W. Kohn and L. J. Sham, Phys. Rev., 1965, 140, 1133-1138.
- M. J. Frisch, G. Trucks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, G. Scalmani, V. Barone, B. Mennucci and G. Petersson, Inc.: Wallingford, CT, 2009.
- R. F. Bader, Acc. Chem. Res., 1985, 18, 9-15.
- R. F. Bader, Chem. Rev., 1991, 91, 893-928.
- Tian Lu and Qinxue Chen, “Interaction Region Indicator: A Simple Real Space Function Clearly Revealing Both Chemical Bonds and Weak Interactions,” Chemistry—Methods, 1 (5), 231-239, 2021.
- T. Lu and F. Chen, J. Comput. Chem., 2012, 33, 580-592.
- M. R. Maliyappa, J. Keshavayya, R. A. Shoukat Ali and S. Harisha, “Synthesis, Characterization, Solvatochromic and Biological studies of novel Benzothiazole based azo dyes,” Journal of Chemical and Pharmaceutical Sciences, Special Issue 1 (10-15), 2018.
Toplam 31 adet kaynakça vardır.
Ayrıntılar
| Birincil Dil | İngilizce |
|---|---|
| Konular | Kimya Mühendisliği |
| Bölüm | Makaleler |
| Yazarlar | |
| Proje Numarası | KÜ-BAP01/2019-9 |
| Yayımlanma Tarihi | 22 Haziran 2023 |
| Yayımlandığı Sayı | Yıl 2023 Cilt: 18 Sayı: 2 |
