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

Default Image

PDF CIF FILE

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

Section

Research Article

Issue

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

Dates

Received 2020-08-13
Accepted 2020-09-26
Published 2020-12-31

Crossmark

Thierno Moussa Seck

eMail

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

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

Fatou Dieng Faye

eMail

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

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

Aissatou Alioune Gaye

eMail

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

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

Ibrahima Elhadji Thiam

eMail

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

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

Ousmane Diouf

eMail

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

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

Mohamed Gaye

eMail

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

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

Pascal Retailleau

eMail

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)°.

This Abstract was viewed 1459 times |

Article PDF downloaded 701 times

Article CIF FILE downloaded 0 times

How to Cite

(1)

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.

Share

Links for Article

Crossref - Scopus - Google - European PMC

Crossref

Scopus

Google Scholar

Europe PMC

References

[1]. Curtius, T.; Heidenreich, K. Berichte Dtsch. Chem. Ges. 1894, 27, 773-774.
https://doi.org/10.1002/cber.189402701150

[2]. Wu, Y. Y.; Shao, W. B.; Zhu, J. J.; Long, Z. Q.; Liu, L. W.; Wang, P. Y.; Li, Z.; Yang, S. J. Agric. Food Chem. 2019, 67, 13892-13903.
https://doi.org/10.1021/acs.jafc.9b05942

[3]. Liu, Y.; Song, H.; Huang, Y.; Li, J.; Zhao, S.; Song, Y.; Yang, P.; Xiao, Z.; Liu, Y.; Li, Y.; Shang, H.; Wang, Q. J. Agric. Food Chem. 2014, 62, 9987-9999.
https://doi.org/10.1021/jf503794g

[4]. Huang, Z.; Liu, Y.; Li, Y.; Xiong, L.; Cui, Z.; Song, H.; Liu, H.; Zhao, Q.; Wang, Q. J. Agric. Food Chem. 2011, 59, 635-644.
https://doi.org/10.1021/jf104196t

[5]. Ragno, R.; Coluccia, A.; La Regina, G.; De Martino, G.; Piscitelli, F.; Lavecchia, A.; Novellino, E.; Bergamini, A.; Ciaprini, C.; Sinistro, A.; Maga, G.; Crespan, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 3172-3184.
https://doi.org/10.1021/jm0512490

[6]. Palomo, V.; Perez, D. I.; Roca, C.; Anderson, C.; Rodriguez-Muela, N.; Perez, C.; Morales-Garcia, J. A.; Reyes, J. A.; Campillo, N. E.; Perez-Castillo, A. M.; Rubin, L. L.; Timchenko, L.; Gil, C.; Martinez, A. J. Med. Chem. 2017, 60, 4983-5001.
https://doi.org/10.1021/acs.jmedchem.7b00395

[7]. Heo, D. N.; Alioglu, M. A.; Wu, Y.; Ozbolat, V.; Ayan, B.; Dey, M.; Kang, Y.; Ozbolat, I. T. ACS Appl. Mater. Interfaces 2020, 12, 20295-20306.
https://doi.org/10.1021/acsami.0c05096

[8]. Cosper, D. R.; Kowalski, D. J. Ind. Eng. Chem. Res. 1990, 29, 1130-1136.
https://doi.org/10.1021/ie00103a007

[9]. Hruskova, K.; Potuckova, E.; Opalka, L.; Hergeselova, T.; Haskova, P.; Kovarikova, P.; Simunek, T.; Vavrova, K. Chem. Res. Toxicol. 2018, 31, 435-446.
https://doi.org/10.1021/acs.chemrestox.7b00324

[10]. Hanna, M. M. Eur. J. Med. Chem. 2012, 55, 12-22.
https://doi.org/10.1016/j.ejmech.2012.06.048

[11]. Bharadwaj, S. S.; Poojary, B.; Nandish, S. K. M.; Kengaiah, J.; Kirana, M. P.; Shankar, M. K.; Das, A. J.; Kulal, A.; Sannaningaiah, D. ACS Omega 2018, 3, 12562-12574.
https://doi.org/10.1021/acsomega.8b01476

[12]. Zaki, R. M.; Kamal El-Dean, A. M.; Radwan, S. M.; Sayed, A. S. A. ACS Omega 2020, 5, 252-264.
https://doi.org/10.1021/acsomega.9b02604

[13]. Tripathi, L.; Singh, R.; Stables, J. P. Eur. J. Med. Chem. 2011, 46, 509-518.
https://doi.org/10.1016/j.ejmech.2010.11.030

[14]. Abdel-Aziz, M.; Abuo-Rahma, G. E. D. A.; Hassan, A. A. Eur. J. Med. Chem. 2009, 44, 3480-3487.
https://doi.org/10.1016/j.ejmech.2009.01.032

[15]. Zhang, L.; Shi, L.; Soars, S. M.; Kamps, J.; Yin, H. J. Med. Chem. 2018, 61, 5881-5899.
https://doi.org/10.1021/acs.jmedchem.7b01557

[16]. Kumar, G.; Krishna, V. S.; Sriram, D.; Jachak, S. M. Eur. J. Med. Chem. 2018, 156, 871-884.
https://doi.org/10.1016/j.ejmech.2018.07.047

[17]. Wright, J. B.; Dulin, W. E.; Markillie, J. H. J. Med. Chem. 7, 1964, 102-105.
https://doi.org/10.1021/jm00331a022

[18]. Das Mukherjee, D.; Kumar, N. M.; Tantak, M. P.; Das, A.; Ganguli, A.; Datta, S.; Kumar, D.; Chakrabarti, G. Biochemistry 2016, 55, 3020-3035.
https://doi.org/10.1021/acs.biochem.5b01127

[19]. Li, J.; Zhang, L.; Xu, G. C.; Yu, W. X.; Jia, D. Z. Inorg. Chem. Commun. 2014, 45, 40-43.
https://doi.org/10.1016/j.inoche.2014.03.042

[20]. Mandal, T. N.; Roy, S.; Konar, S.; Jana, A.; Ray, S.; Das, K.; Saha, R.; El Fallah, M. S.; Butcher, R. J.; Chatterjee, S.; Kar, S. K. Dalton Trans. 2011, 40, 11866-11875.
https://doi.org/10.1039/c1dt10813a

[21]. Seck, T. M.; Diop, M.; Diouf, D.; Diouf, O.; Barry, A. H.; Gaye, M. IOSR J. Appl. Chem. 2018, 11, 6-14.

[22]. Sow, M. M.; Diouf, O.; Gaye, M.; Sall, A. S. S.; Castro, G.; Perez-Lourido, P.; Valencia, L.; Caneschi, A.; Sorace, L. Cryst. Growth Des. 2013, 13, 4172-4176.
https://doi.org/10.1021/cg400885f

[23]. Novak, P.; Jednacak, T.; Vukovic, J. P.; Zangger, K.; Rubcic, M.; Galic, N.; Hrenar, T. Croat. Chem. Acta 2012, 85, 451-456.
https://doi.org/10.5562/cca2123

[24]. Sheldrick, G. M. Acta Crystallogr. A 2015, 71, 3-8.
https://doi.org/10.1107/S2053273314026370

[25]. Sheldrick, G. M. Acta Crystallogr. C 2015, 71, 3-8.
https://doi.org/10.1107/S2053273314026370

[26]. Farrugia, L. J. J. Apply. Crystallogr. 1997, 30, 565-565.
https://doi.org/10.1107/S0021889897003117

[27]. Akhtar, P.; Yaakob, Z.; Ahmed, Y.; Shahinuzzaman, M.; Hyder, M. K. M. Asian J. Chem. 2018, 30, 365-370.
https://doi.org/10.14233/ajchem.2018.20980

[28]. Singh, A. K.; Pandey, O. P; Sengupta, S. K. Spectrochim. Acta A 2013, 113, 393-399.
https://doi.org/10.1016/j.saa.2013.04.045

[29]. Seck, T. M.; Sy, A.; Lo, D.; Gaye, P. A.; Sall, M. L.; Diouf, O.; Diaw, M.; Gaye, M. Open J. Inorg. Chem. 2019, 9, 35-52.
https://doi.org/10.4236/ojic.2019.94004

[30]. Tamboura, F. B.; Diouf, O.; Barry, A. H.; Gaye, M.; Sall, A. S. Polyhedron 2012, 13, 97-103.
https://doi.org/10.1016/j.poly.2012.06.025

[31]. Datta, R.; Vittalacharya, R.; Gudennavar, B. S. Eur. J. Chem. 2014, 5(3), 394-396.
https://doi.org/10.5155/eurjchem.5.3.394-396.1043

[32]. Sylla-Gueye, R.; Thiam, I. E.; Orton, J.; Coles, S.; Gaye, M. Acta Crystallogr. E 2020, 76, 660-663.
https://doi.org/10.1107/S205698902000465X

[33]. Gueye, M. N.; Dieng, M.; Thiam, I. E.; Lo, D.; Barry, A. H.; Gaye, M.; Retailleau, P. S. Afr. J. Chem. 2017, 70, 8-15
https://doi.org/10.17159/0379-4350/2017/v70a2

[34]. Bikas, R.; Anarjan, P. M.; Tiekink, E. R. T. Acta Crystallogr. E 2012, 68, o193-o193.
https://doi.org/10.1107/S1600536811053268

[35]. Rubcic, M.; Galic, N.; Halasz, I.; Jednacak, T.; Judas, N.; Plavec, J.; Sket, P.; Novak, P. Cryst. Growth Des. 2014, 14, 2900-2912.
https://doi.org/10.1021/cg500203k

[36]. Bacchi, A.; Bonini, A.; Carcelli, M.; Ferraro, F.; Leporati, E.; Pelizzi, C.; Pellizi, G. J. Chem. Soc. Dalton Trans. 1996, 2699-2704.
https://doi.org/10.1039/dt9960002699

[37]. Tandon, S. S.; Dul, M. C.; Lee, J. L.; Dawe, L. N. M.; Anwar, U.; Thompson, L. K. Dalton Trans. 2011, 40, 3466-3475.
https://doi.org/10.1039/c0dt01487g

[38]. Feng, Y. L.; Zhang, F. X.; Yu, J. X.; Jiang, W. J.; Kuang, D. Z. Chin. J. Inorg. Chem. 2018, 34, 1857-1863.

[39]. Foti, M. C.; Daquino, C.; Geraci, C. J. Org. Chem. 2004, 69, 2309-2314.
https://doi.org/10.1021/jo035758q

[40]. Taha, Z. A.; Ajlouni, A. M.; Al-Momani, W.; AlGhzawi, A. A. Spectrochim. Acta A 2011, 81, 570-577.
https://doi.org/10.1016/j.saa.2011.06.052

Supporting Agencies

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

Most read articles by the same author(s)

Most read articles by the same author(s)

Amadou Gueye, Farba Bouyagui Tamboura, Jean-Marc Planeix, Nathalie Gruber, Mohamed Gaye, Synthesis and spectroscopic study of transition metal complexes of tridentate ligand formed by direct condensation of o-vanillin and 2-aminophenol: X-ray structural characterization of the zinc(II) complex , European Journal of Chemistry: Vol. 9 No. 4 (2018): December 2018
Mamour Sarr, Mayoro Diop, Ibrahima Elhadj Thiam, Mohamed Gaye, Aliou Hamady Barry, Natalia Alvarez, Javier Ellena, Co-crystal structure of a dinuclear (Zn-Y) and a trinuclear (Zn-Y-Zn) complexes derived from a Schiff base ligand , European Journal of Chemistry: Vol. 9 No. 2 (2018): June 2018
Pokpa Haba, Adama Sy, Farba Bouyagui Tamboura, Mamour Sarr, Ibrahima Elhadji Thiam, Aliou Hamady Barry, Mohamed Lamine Sall, Mohamed Gaye, Pascal Retailleau, Synthesis, spectroscopic studies and X-ray structure determination of two mononuclear copper complexes derived from the Schiff base ligand N,N-dimethyl-N'-((5-methyl-1H-imidazol-4-yl)methylene)ethane-1,2-diamine , European Journal of Chemistry: Vol. 10 No. 3 (2019): September 2019
Mbosse Ndiaye Gueye, Moussa Dieng, Djiby Lo, Ibrahima Elhadji Thiam, Aliou Hamady Barry, Mohamed Gaye, Abdou Salam Sall, Pascal Retailleau, Synthesis, physical studies and crystal structure determination of Y(III) and Er(III) complexes of 1-(pyridin-2-yl)-2-(pyridine-2-ylmethylene)hydrazine , European Journal of Chemistry: Vol. 8 No. 2 (2017): June 2017
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: Vol. 12 No. 2 (2021): June 2021
Modou Lo, Andrea Martínez, Hugo Santalla, Fátima Garrido, Aliou Hamady Barry, Mohamed Gaye, Synthesis and X-ray crystallography of (1R,3aR,7aR)-1-((S)-1-((2R,5S)-5-(3-hydroxypentan-3-yl)tetrahydrofuran-2-yl)ethyl)-7a-methyloctahydro-4H-inden-4-one , European Journal of Chemistry: Vol. 8 No. 3 (2017): September 2017
Cheikh Ndoye, Gregory Excoffier, Gorgui Awa Seck, Ousmane Diouf, IbraIbrahima Elhadji Thiam, Mamadou Sidibe, Mohamed Gaye, Crystal structures of bis[1-(1-hydroxypropan-2-ylidene)thiosemicarbazide-κ3S,N,O)cobalt(III)-tetra(thiocyanato-κN) cobalt(II) methanol solvate, bis{1-(1-hydroxypropan-2-ylidene)thiosemicarbazide-κ3S,N,O}nickel(II) bis(thiocyanate) and (1-(1-hydroxypropan-2-ylidene)thiosemicarbazide-κ3S,N,O)bis(thiocyanato-κN)zinc(II) , European Journal of Chemistry: Vol. 13 No. 2 (2022): June 2022

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).