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

Issue cover




Crossmark

  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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)°.


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).

2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).

3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


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

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.11.4.285-290.2023

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1127 times | icon graph PDF Article downloaded 448 times

Funding information


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

Citations

/


[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
/

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 information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


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. 27 Sep. 2023
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)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



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


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



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

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c) 2020 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/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 (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).


© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.