European Journal of Chemistry 2020, 11(4), 285-290 | doi: https://doi.org/10.5155/eurjchem.11.4.285-290.2023 | Get rights and content

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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


Thierno Moussa Seck (1) orcid , Fatou Dieng Faye (2) orcid , Aissatou Alioune Gaye (3) orcid , Ibrahima Elhadji Thiam (4) orcid , Ousmane Diouf (5) orcid , Mohamed Gaye (6,*) orcid , Pascal Retailleau (7) orcid

(1) Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal
(2) Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal
(3) Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal
(4) Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal
(5) Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal
(6) Department of Chemistry, University Cheikh Anta Diop, Dakar, 10700, Sénégal
(7) 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
(*) Corresponding Author

Received: 13 Aug 2020 | Revised: 23 Sep 2020 | Accepted: 26 Sep 2020 | Published: 31 Dec 2020 | Issue Date: December 2020

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 (Rsigma = 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)°.


Keywords


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

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DOI: 10.5155/eurjchem.11.4.285-290.2023

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Funding information


The Fondation Sonatel, http://fondationsonatel.sn/ , Senegal

Citations

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[1]. Moussa Faye, Mouhamadou Moustapha Sow, Papa Aly Gaye, Moussa Dieng, Mohamed Gaye
Crystal structures of bis-{N-[1-(pyridin-2-yl-κN)ethylidene]nicotine hydrazide-κ2N’,O}cobalt(II)bis(perchlorate) dihydrate and bis-{N'-[1-(pyridin-2-yl-κN)ethylidene]nicotinohydrazide-κ2N',O}copper(II) perchlorate
European Journal of Chemistry  12(2), 159, 2021
DOI: 10.5155/eurjchem.12.2.159-164.2074
/


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Seck, T.; Faye, F.; Gaye, A.; Thiam, I.; Diouf, O.; Gaye, M.; Retailleau, P. Eur. J. Chem. 2020, 11(4), 285-290. doi:10.5155/eurjchem.11.4.285-290.2023
Seck, T.; Faye, F.; Gaye, A.; Thiam, I.; 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(4), 285-290. doi:10.5155/eurjchem.11.4.285-290.2023
Seck, T., Faye, F., Gaye, A., Thiam, I., Diouf, O., Gaye, M., & Retailleau, P. (2020). 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, 11(4), 285-290. doi:10.5155/eurjchem.11.4.285-290.2023
Seck, Thierno, Fatou Dieng Faye, Aissatou Alioune Gaye, Ibrahima Elhadji Thiam, Ousmane Diouf, Mohamed Gaye, & Pascal Retailleau. "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 [Online], 11.4 (2020): 285-290. Web. 25 Sep. 2021
Seck, Thierno, Faye, Fatou, Gaye, Aissatou, Thiam, Ibrahima, Diouf, Ousmane, Gaye, Mohamed, AND Retailleau, Pascal. "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 [Online], Volume 11 Number 4 (31 December 2020)

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