New Nitro Diazo Dye Vanillin Derivatives, Synthesis and Characterization
DOI:
https://doi.org/10.22401/pvgazv05Keywords:
Nitro , Vanillin , Diazo dye , UV-Vis spectroscopy , FTIR spectroscopyAbstract
The diverse applications of azo compounds as reagents to bring about chemical synthesis is one of the fastest-growing areas of research. It is well known that the position of the substituents has an important role in the effect of the medicinal, dye industry, thermal, and optical properties of the compounds. In this work, we limit our studies to synthesizing two new diazo dye vanillin derivatives starting from aniline. Nitro aniline compounds 10 and 12 were prepared starting from aniline, and new nitro diazo vanillin derivatives were obtained 4 and 5. Through coupling reactions with vanillin 15 via diazonium salts, 4-hydroxy-3-methoxy-5-((2,4-dinitrophenyl)diazenyl)benzaldehyde 4 was obtained from 2,4-dinitroaniline 10, while 4-hydroxy-3-methoxy-5-((2,4-6,trinitrophenyl)diazenyl)benzaldehyde 5 resulted from 2,4,6-trinitroaniline 12. The synthesized compounds were characterized by spectroscopic methods; UV-Vis., FTIR, MS, and 1HNMR and melting point determination. The results of the reactions gave good yields of all products.
References
Al–Shara’ey A.A.; Al–Douh M.H. and Gahnem Y.S.; “Synthesis and antimicrobial study of some polycyclic Compounds by [3+2] cycloaddition reactions of aldazines with N-aryl maleimides”. TOJSAT, 9(1): 80-90, 2019. Available in: http://www.tojsat.net/?pid=show issue&issueid=215
Al–Shara’ey A.A.; Al–Douh M.H.; Thabet E.A. and Gahnem Y.S.; “Synthesis of new heterocyclic compounds from reaction of N-aryl maleimide with cinnamal aryl hydrazones and their antimicrobial activity”. Intern. J. Chem. Stud., 3(3): 36-45, 2019. Available in: https:// www.chemistryjournal.in/assets/archives/2019/vol3issue3/3-3-12-158.pdf
Ahmad S.M.; Al-Taie Z.S.; Al-Mashhadani M.H.; Hammza R.A.; Rahmansyah M.; Bufaroosha M. and Yousif E.; “An overview of preparation for different azo compounds”. ANJS, 27(1): 1-13, 2024. DOI: 10.22401/ANJS .27.1.01
Abdulhameed Z.A. and Alabdali A.J.; “Synthesis, characterization and antimicrobial evolution of new bi-α-amino nitrile compounds”. ANJS, 26(4): 21-27, 2023. DOI: 10.22401/ANJS.26.4.03
Al–Douh M.H.; Selim E.A.B.; Al–Haik W.M.; Mahram S.M.B.; Al–Bakri A.K.; Al–Nohey D.S. and Sonbol K.S.; “Synthesis and antimicrobial activity of some compounds derived from diazo dyes”. Intern. J. Chem. Stud., 3(4): 6-12, 2019. Available in: https://www.chemistryjournal.in/ assets/archives/2019/vol3issue4/3-3-16-572.pdf
Selim E.A.B. and Al–Douh M.H.; “Unusual effects of intramolecular hydrogen bonds and dipole interaction on FTIR and NMR of some imines”. Asian J. Appl. Chem. Res., 3(3): 1-6, 2019. DOI: 10.9734/AJACR/2019/v3i330096
Al–Douh M.H.; Selim E.A.B.; Salim H.A.M. and Abdullah H.H.; “Molecular structure and spectroscopic studies of some diazo dyes compounds using DFT Method”. IEEE. [The first International Conference of Intelligent Computing and Engineering ICOICE-2019, Mukalla, Hadhramout, Yemen. Computing and Engineering], 49: 1-4, 2019. DOI: 10.1109/ICOICE48418.2019.9035176
Al–Douh M.H.; Selim E.A.B.; Tahir E.M.; Esmail S.A.A.; Naji Y.A. and Abdullah H.H.; “Biophysical study for the interactions of some diazo dyes with human serum albumin”. Asian J. Appl. Chem. Res., 4(3): 1-10, 2019. DOI: 10.9734/AJACR/2019/v4i330113
Al–Douh M.H.; Selim E.A.B.; Abdullah H.H.; Abdullah H.Y.; Al–Bakri A.K.; Al–Nohey D.S.; Mahram S.M.B.; Yusr K.M. and Hawiel F.A.B.; “Molecular docking study of some nitro diazo dye derivatives as antiviral candidates of COVID-19”. Asian J. Appl. Chem. Res., 8(8): 8-15, 2021. DOI: 10.9734/AJACR/2021/v8i23018 7
Delta NMR Software Jeol, Jeol Resonance Inc. Release Notes, V 5.3.1, 2019.
Silverstein R.M.; Webster F.X. and Kiemle D.J.; “Spectrometric Identification of Organic Compounds”, 7th Ed., Wiley-VCH, New York, USA. ISBN: 0471393622, 2005
So B.K.; Kim H.J.; Lee S.M.; Song H.H. and Park J.H.; “Novel bent-shaped liquid crystalline compounds: IV. Dimesogenic compounds containing 2-hydroxy-1,3-dioxy propylene and azobenzene mesogens. Dyes Pigments, 70(1):38-42, 2006. DOI: 10.1016/ j.dyepig.2005.04.006
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Copyright (c) 2024 Elham Abdalrahem Bin Selim, Mohammed Hadi Al–Douh, Khulood Mahfoudh Yusr
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