Synthesis of mono and bis-substituted asymmetrical compounds, (1-(pyridin-2-yl)ethylidene)carbonohydrazide and 1-(2'-hydroxybenzylidene)-5-(1'-pyridylethylidene)carbonohydrazone: Structural characterization and antioxidant activity study | European Journal of Chemistry

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Published: Dec 31, 2020

DOI: https://doi.org/10.5155/eurjchem.11.4.285-290.2023

Keywords:

Schiff base, Salicylaldehyde, Carbohydrazide, 2-Acetylpyridine, Antioxidant activity, Single crystal structure

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Research Article

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Vol. 11 No. 4 (2020): December 2020

Dates

Received 2020-08-13
Accepted 2020-09-19
Published 2020-12-31

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Thierno Moussa Seck

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Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal

http://orcid.org/0000-0002-7611-0367

Fatou Dieng Faye

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Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal

http://orcid.org/0000-0002-2857-5426

Aissatou Alioune Gaye

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Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal

http://orcid.org/0000-0002-8510-6140

Ibrahima Elhadji Thiam

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Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal

http://orcid.org/0000-0002-4595-8445

Ousmane Diouf

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Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal

http://orcid.org/0000-0003-3475-9528

Mohamed Gaye

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Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal

http://orcid.org/0000-0001-8989-1548

Pascal Retailleau

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Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France

http://orcid.org/0000-0003-3995-519X

Abstract

Carbonohydrazide was used for synthetizing a new dissymmetrical bis-substituted Schiff base 1-(2'-hydroxybenzylidene)-5-(1'-pyridylethylidene)carbonohydrazone (2). A mono substituted compound (1-(pyridin-2-yl)ethylidene)carbonohydrazide (1) was firstly prepared by condensation reaction of carbonohydrazide and 2-acetylpyridine in 1:1 ratio. Secondly, compound 2 was obtained by condensation reaction of compound 1 and salicylaldehyde in 1:1 ratio. The prepared compounds were characterized by elemental analysis, infrared and ¹H and ¹³C NMR spectroscopy techniques, and the structure of compound 2 was determined by single-crystal X-ray diffraction study. The compound 2 (C₁₅H₁₅N₅O₂) crystallises in the monoclinic space group P2₁/c with the following unit cell parameters: a = 8.3683(3) Å, b = 13.9986(4) Å, c = 12.1610(4) Å, β = 97.512(3)°, V = 1412.37(8) Å³, Z = 4, T = 100(2) K, μ(MoKα) = 0.098 mm^-1, Dcalc = 1.398 g/cm³, 6057 reflections measured (5.708° ≤ 2Θ ≤ 54.962°), 6057 unique (R_sigma = 0.0395) which were used in all calculations. The final R₁ was 0.0474 (I > 2σ(I)) and wR₂ was 0.1971 (all data). The oxygen atom O1 and the azomethine nitrogen atom N5 adopt cis-configuration relative to the C8-N4 bond, while O1 adopts trans-configuration with the azomethine nitrogen atom N2 relative to C8-N3 bond. The crystal packing of compound 2 is stabilized by intramolecular O(phenol)–H···N(carbohydrazide) and intermolecular N (carbohydrazide)–H···O (carbo-hydrazide) hydrogen bonds which form layers parallel to [010] axis. Additional C–H···O hydrogen bond consolidate the structure. The carbonohydrazide moiety C=N–N–C(O)–N–N=C fragment and the phenyl ring are almost coplanar; with an angle of 1.73(1)° between their means plans. The dihedral angle between the mean planes of the phenyl and the pyridine rings is 22.267(2)°.

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Seck, T. M.; Faye, F. D.; Gaye, A. A.; Thiam, I. E.; Diouf, O.; Gaye, M.; Retailleau, P. Synthesis of Mono and Bis-Substituted Asymmetrical Compounds, (1-(pyridin-2-yl)ethylidene)carbonohydrazide and 1-(2’-Hydroxybenzylidene)-5-(1’-pyridylethylidene)carbonohydrazone: Structural Characterization and Antioxidant Activity Study. Eur. J. Chem. 2020, 11, 285-290.

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