Synthesis and Theoretical Calculations of Benzoic Acid-Based New Mono Azo Dye

Abstract

This study describes the synthesis, characterization and theoretical calculation of 3,5-dihydroxy-2-(naphthalen-2-yldiazenyl) benzoic acid. The synthesized compound was obtained through efficient synthetic route using 2-Naphthylamine and 3,5-dihydroxybenzoic acid as starting materials and characterized by various spectroscopic techniques such as Fouirer Transform Infrared Spectroscopy (FTIR), Proton Nuclear Magnetic Resonance Spectroscopy (1H-NMR), Carbon Nuclear Magnetic Resonance Spectroscopy (13C-NMR), Ultraviolet–visible spectroscopy (UV-Vis). All theoretical calculation was performed with Density Functional Theory (DFT). Optimized molecular structure, vibrational spectra, NMR chemical shift values, frontier molecular orbitals, bond lengths (Å), bond angles (°) and Molecular Electrostatic Potential (MEP) diagram of molecule were calculated using the 6-311G(d,p) basis set. It has been observed that the results obtained from the experimental and theoretical calculations support each other and were in harmony.

Keywords

• Benzoic acid
• Mono azo dye
• Theoretical Calculation

Benzoik Asit Bazlı Yeni Azo Boyar Madde Sentezi ve Teorik Hesaplamaları

Abstract

Bu çalışmada 3,5-dihidroksi-2-(naftalen-2-ildiazenil) benzoik asidin sentezi, karakterizasyonu ve teorik hesaplaması anlatılmaktadır. Sentezlenen bileşik, başlangıç malzemeleri olarak 2-Naftilamin ve 3,5-dihidroksibenzoik asit kullanılarak verimli sentetik yoldan elde edildi ve Fourier Dönüşümlü Kızılötesi Spektroskopisi (FTIR), Proton Nükleer Manyetik Rezonans Spektroskopisi (1H-NMR), Karbon Nükleer Manyetik Rezonans Spektroskopisi (13C-NMR), Ultraviyole-Görünür Spektroskopi (UV-Vis) gibi çeşitli spektroskopik tekniklerle karakterize edildi. Tüm teorik hesaplamalar Yoğunluk Fonksiyonel Teorisi (DFT) ile yapıldı. Optimize edilmiş moleküler yapı, titreşim spektrumları, NMR kimyasal kayma değerleri, sınır moleküler orbitalleri, bağ uzunlukları, bağ açıları ve molekülün Moleküler Elektrostatik Potansiyel (MEP) diyagramı 6-311G(d,p) temel seti kullanılarak hesaplandı. Deneysel ve teorik hesaplamalardan elde edilen sonuçların birbirini desteklediği ve uyum içinde olduğu görüldü.

Keywords

• Benzoik asit
• Mono azo boya
• Teorik hesaplama

References

1. S. Liu, H. Xue, X. Feng, and S. Pyo, “Electrostimulation for promoted microbial community and enhanced biodegradation of refractory azo dyes,” J. Environ. Chem. Eng.,10, 108626, 2022.
2. F. Tsukasa, M. Keisuke, H. Yoshihiro, K. Susumu, and N. Hiroyuki, “Design, synthesis, and evaluation of azo D–π-A dyes as photothermal agents,” Org. Biomol. Chem., 18(1), 93–101, 2020.
3. X. Li, C. P. Chen, H. Gao, Z. He, Y. Xiong, H. Li, W. Hu, Z. Ye, G. He, J. Lu, and Y. Su, “Video-rate holographic display using azo-dye-doped liquid crystal.” J. Disp. Technol., 10(6), 438–443, 2014.
4. A. Ozarslan, D. Çakmak, F. Erol, H. Şenöz, N. Seferoğlu, A. Barsella, and Z. Seferoğlu, “Synthesis and investigation of photophysical, NLO and thermal properties of D-π-A-π-D dyes,” J. Mol. Struct., 1229, 129583, 2021.
5. B. Derkowska-Zielinska, E. Gondek, M. Pokladko-Kowar, A. Kaczmarek-Kedziera, A. Kysil, G. Lakshminarayana, and O. Krupka, “ Photovoltaic cells with various azo dyes as components of the active layer.” Sol. Energy, 203, 19–24, 2020.
6. X. Zhang, K. Fang, H. Zhou, K. Zhang, and M. N. Bukhari, “Enhancing inkjet image quality through controlling the interaction of complex dye and diol molecules,” J. Mol. Liq., 312, 113481, 2020.
7. D. Yousif Fnfoon, and K. J. Al-Adilee, “Synthesis and spectral characterization of some metal complexes with new heterocyclic azo imidazole dye ligand and study biological activity as anticancer,” J. Mol. Struct., 1271, 134089, 2023.
8. H. D. Trivedi, B.Y. Patel, P. K. Patel, and S.R. Sagar, “Synthesis, molecular modeling, ADMET and fastness studies of some quinoline encompassing pyrimidine azo dye derivatives as potent antimicrobial agents,” Chem. Data Collect., 41, 100923, 2022.

9. R. Sahilu, R. Eswaramoorthy, E. Mulugeta, and A. Dekebo, “Synthesis, DFT analysis, dyeing potential and evaluation of antibacterial activities of azo dye derivatives combined with in-silico molecular docking and ADMET predictions,” J. Mol. Struct., 1265, 133279, 2022.
10. K. Yamjala, M.S. Nainar, N. R. Ramisetti, “Methods for the analysis of azo dyes employed in food industry – A review,” Food Chem., 192, 813-824, 2016.
11. O. Yerlikaya, L. Gucer, E. Akan, S. Meric, E. Aydin, and O. Kinik, “Benzoic acid formation and its relationship with microbial properties in traditional Turkish cheese varieties,” Food Biosci., 41, 101040, 2021.
12. E. Mikami, T. Goto, T. Ohno, H. Matsumoto, and M. Nishida, “Simultaneous analysis of dehydroacetic acid, benzoic acid, sorbic acid and salicylic acid in cosmetic products by solid-phase extraction and high-performance liquid chromatography,” J. Pharm. Biomed. Analysis, 28, 261–267, 2002.
13. Y. J. Heo and K. Lee, “Application of micellar electrokinetic capillary chromatography for the determination of benzoic acid and its esters in liquid formula medicines as preservatives,” J. Pharm. Biomed. Analysis, 17, 1371–1379, 1998.
14. B.-E. Amborab´e, P. Fleurat-Lessard, J.-F. Chollet, and G. Roblin, “Antifungal effects of salicylic acid and other benzoic acid derivatives towards eutypa lata: structure–activity relationship,” Plant Physiol. Biochem., 40(12), 1051–1060, 2002.
15. C. Gadgoli and S.H. Mishra, “Antihepatotoxic activity of p-methoxy benzoic acid from Capparis spinosa,” J. Ethnopharmacol., 66 (2), 187–192, 1999.
16. E.-S. Park, W.-S. Moon, M.-J. Song, M.-N. Kim, K.-H. Chung, and J.-S. Yoon, “Antimicrobial activity of phenol and benzoic acid derivatives,” Int. Biodeterior. Biodegrad., 47 (4), 209–214, 2001.
17. M. Gökalp, B. Dede, T. Tilki, and Ç. Karabacak Atay, “Triazole based azo molecules as potential antibacterial agents: Synthesis, characterization, DFT, ADME and molecular docking studies,” J. Mol. Struct., 1212, 128140, 2020.
18. P. Tunay Tasli, Ç. Karabacak Atay, T. Demirturk, and T. Tilki, “Experimental and computational studies of newly synthesized azo dyes based materials,” J. Mol. Struct., 1201, 127098, 2020.
19. Ç. Karabacak Atay, F. Duman, M. Gokalp, T. Tilki, and S. Ozdemir Kart, “A rapid synthesis of 2-((2-amino-4,6-dimethylpyrimidine-5yl)diazenyl)benzoic acid: Experimental, DFT study and DNA cleavage activity,” J. Mol. Struct., 1171, 906-914, 2018.
20. F. Yıldırım, A. Demirçalı, A. Oztürk Kiraz, and F. Karcı, “Synthesis of some new pyrazolo[5,1-c][1,2,4]triazine derivatives and computational study,” J. Mol. Struct., 1222, 128850, 2020.
21. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, G.A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B.G. Janesko, R. Gomperts, B. Mennucci, H.P. Hratchian, J.V. Ortiz, A.F. Izmaylov, J.L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V.G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, J.M. Millam, M. Klene, C. Adamo, R. Cammi, J.W. Ochterski, R.L. Martin, K. Morokuma, O. Farkas, J.B. Foresman, D.J. Fox, Gaussian 09, Revision E.01, Gaussian, Inc., Wallingford CT, 2016.
22. A.D. Becke, “Density-functional exchange-energy approximation with correct asymptotic behaviour,” Phys. Rev. A., 38, 3098-3100, 1988.
23. C. Lee, W. Yang, and R.G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Phys. Rev. B., 37, 785-789, 1988.
24. K. Wolinski, J.F. Hinton, and P. Pulay, “Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations,” J. Am. Chem. Soc., 112, 8251-8260, 1990.