Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach
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2019
Authors
Milovanović, Vesna M.Petrović, Zorica D.
Novaković, Slađana B.
Bogdanović, Goran A.
Simijonović, Dušica
Petrović, Vladimir P.
Article (Published version)
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© 2019 Elsevier B.V.
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Simple, one-pot, and low-cost reactions of acetylacetone with a variety of substituted benzoyl hydrazides in lemon juice, as eco-friendly medium, were performed. In reactions of benzoyl hydrazides with electron-donating groups on phenyl ring, the 1-benzoyl-1H-pyrazole derivatives were obtained in short reaction time, and in good to high yields. On the other hand, benzoyl hydrazides with electron-withdrawing groups reacted slower, yielding the mixture of 1-benzoyl-5-hydroxy-4,5-dihydro-1H-pyrazole and benzoyl-1H-pyrazole derivatives. It is worth pointing out that two products, (2-chlorophenyl)(4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)methanone and (4-iodophenyl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone are reported here for the first time. All obtained compounds were characterized using IR, UV–Vis and NMR, experimentally and theoretically, as well as with melting points. Good agreement between experimental and simulated IR, UV–Vis, 1H and 13C NMR spectra was achieved. In addition, c...rystal structures and Hirshfeld surfaces analysis of (4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)(4-iodophenyl)methanone were reported. © 2019 Elsevier B.V.
Keywords:
Spectral characterization / Crystal structure / Density functional theory / Green synthetic procedureSource:
Journal of Molecular Structure, 2019, 1195, 85-94Funding / projects:
- Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes (RS-MESTD-Basic Research (BR or ON)-172016)
- Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds (RS-MESTD-Basic Research (BR or ON)-172014)
DOI: 10.1016/j.molstruc.2019.05.095
ISSN: 0022-2860; 1872-8014
WoS: 000475344800008
Scopus: 2-s2.0-85066467734
URI
https://linkinghub.elsevier.com/retrieve/pii/S0022286019306659https://vinar.vin.bg.ac.rs/handle/123456789/8224
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VinčaTY - JOUR AU - Milovanović, Vesna M. AU - Petrović, Zorica D. AU - Novaković, Slađana B. AU - Bogdanović, Goran A. AU - Simijonović, Dušica AU - Petrović, Vladimir P. PY - 2019 UR - https://linkinghub.elsevier.com/retrieve/pii/S0022286019306659 UR - https://vinar.vin.bg.ac.rs/handle/123456789/8224 AB - Simple, one-pot, and low-cost reactions of acetylacetone with a variety of substituted benzoyl hydrazides in lemon juice, as eco-friendly medium, were performed. In reactions of benzoyl hydrazides with electron-donating groups on phenyl ring, the 1-benzoyl-1H-pyrazole derivatives were obtained in short reaction time, and in good to high yields. On the other hand, benzoyl hydrazides with electron-withdrawing groups reacted slower, yielding the mixture of 1-benzoyl-5-hydroxy-4,5-dihydro-1H-pyrazole and benzoyl-1H-pyrazole derivatives. It is worth pointing out that two products, (2-chlorophenyl)(4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)methanone and (4-iodophenyl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone are reported here for the first time. All obtained compounds were characterized using IR, UV–Vis and NMR, experimentally and theoretically, as well as with melting points. Good agreement between experimental and simulated IR, UV–Vis, 1H and 13C NMR spectra was achieved. In addition, crystal structures and Hirshfeld surfaces analysis of (4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)(4-iodophenyl)methanone were reported. © 2019 Elsevier B.V. T2 - Journal of Molecular Structure T1 - Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach VL - 1195 SP - 85 EP - 94 DO - 10.1016/j.molstruc.2019.05.095 ER -
@article{ author = "Milovanović, Vesna M. and Petrović, Zorica D. and Novaković, Slađana B. and Bogdanović, Goran A. and Simijonović, Dušica and Petrović, Vladimir P.", year = "2019", abstract = "Simple, one-pot, and low-cost reactions of acetylacetone with a variety of substituted benzoyl hydrazides in lemon juice, as eco-friendly medium, were performed. In reactions of benzoyl hydrazides with electron-donating groups on phenyl ring, the 1-benzoyl-1H-pyrazole derivatives were obtained in short reaction time, and in good to high yields. On the other hand, benzoyl hydrazides with electron-withdrawing groups reacted slower, yielding the mixture of 1-benzoyl-5-hydroxy-4,5-dihydro-1H-pyrazole and benzoyl-1H-pyrazole derivatives. It is worth pointing out that two products, (2-chlorophenyl)(4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)methanone and (4-iodophenyl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone are reported here for the first time. All obtained compounds were characterized using IR, UV–Vis and NMR, experimentally and theoretically, as well as with melting points. Good agreement between experimental and simulated IR, UV–Vis, 1H and 13C NMR spectra was achieved. In addition, crystal structures and Hirshfeld surfaces analysis of (4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)(4-iodophenyl)methanone were reported. © 2019 Elsevier B.V.", journal = "Journal of Molecular Structure", title = "Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach", volume = "1195", pages = "85-94", doi = "10.1016/j.molstruc.2019.05.095" }
Milovanović, V. M., Petrović, Z. D., Novaković, S. B., Bogdanović, G. A., Simijonović, D.,& Petrović, V. P.. (2019). Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach. in Journal of Molecular Structure, 1195, 85-94. https://doi.org/10.1016/j.molstruc.2019.05.095
Milovanović VM, Petrović ZD, Novaković SB, Bogdanović GA, Simijonović D, Petrović VP. Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach. in Journal of Molecular Structure. 2019;1195:85-94. doi:10.1016/j.molstruc.2019.05.095 .
Milovanović, Vesna M., Petrović, Zorica D., Novaković, Slađana B., Bogdanović, Goran A., Simijonović, Dušica, Petrović, Vladimir P., "Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach" in Journal of Molecular Structure, 1195 (2019):85-94, https://doi.org/10.1016/j.molstruc.2019.05.095 . .