European Journal of Chemistry

Synthesis, crystal structure, and spectroscopic characterization of a new non-centrosymmetric compound, 1-(2-chloroquinolin-3-yl)-N-(4-fluorobenzyl)methanimine


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Maha Hachicha
Rawia Nasri
Mohamed Faouzi Zid
Hedi Mrabet


In this work, we report the synthesis and characterization of a new condensed aromatic heterocycle (1-(2-chloroquinolin-3-yl)-N-(4-fluorobenzyl)methanimine) useful in various fields, mainly in medicinal and therapeutic chemistry, with interesting biological properties. Characterization of the title compound was carried out by 1H, 13C, 19F nuclear magnetic resonance and X-ray diffraction techniques. The crystal structure reveals that title compound crystallizes in the monoclinic system and crystal data for C17H12ClFN2: monoclinic, space group P21 (no. 4), a = 7.2253(10) Å, b = 5.7720(10) Å, c = 17.105(2) Å, β = 95.338(10)°, = 710.26(18) Å3, Z = 2, T = 298(2) K, μ(MoKα) = 0.274 mm-1, Dcalc = 1.397 g/cm3, 5010 reflections measured (4.784° ≤ 2Θ ≤ 54.324°), 3160 unique (Rint = 0.0501, Rsigma = 0.0506) which were used in all calculations. The final R1 was 0.0339 (I > 2σ(I)) and wR2 was 0.0907 (all data). The obtained molecular structure has an antiparallel arrangement of the molecular unit leading to a one-dimensional framework.

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How to Cite
Hachicha, M.; Nasri, R.; Zid, M. F.; Mrabet, H. Synthesis, Crystal Structure, and Spectroscopic Characterization of a New Non-Centrosymmetric Compound, 1-(2-Chloroquinolin-3-Yl)-N-(4-fluorobenzyl)methanimine. Eur. J. Chem. 2024, 15, 25-30.

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[1]. Hernández-Ayala, L. F.; Guzmán-López, E. G.; Galano, A. Quinoline derivatives: Promising antioxidants with neuroprotective potential. Antioxidants (Basel) 2023, 12, 1853.

[2]. Kucharski, D. J.; Jaszczak, M. K.; Boratyński, P. J. A review of modifications of quinoline antimalarials: Mefloquine and (hydroxy)chloroquine. Molecules 2022, 27, 1003.

[3]. Loiseau, P. M.; Balaraman, K.; Barratt, G.; Pomel, S.; Durand, R.; Frézard, F.; Figadère, B. The potential of 2-substituted quinolines as antileishmanial drug candidates. Molecules 2022, 27, 2313.

[4]. Zeleke, D.; Eswaramoorthy, R.; Belay, Z.; Melaku, Y. Synthesis and antibacterial, antioxidant, and molecular docking analysis of some novel quinoline derivatives. J. Chem. 2020, 2020, 1-16.

[5]. Abdelbaset, M. S.; Abdel-Aziz, M.; Abuo-Rahma, G. E.-D. A.; Abdelrahman, M. H.; Ramadan, M.; Youssif, B. G. M. Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities. Arch. Pharm. (Weinheim) 2018, 352, 1800270.

[6]. Chauhan, M. S. S.; Umar, T.; Aulakh, M. K. Quinolines: Privileged scaffolds for developing new anti‐neurodegenerative agents. ChemistrySelect 2023, 8 (14), e202204960.

[7]. Rani, A.; Sharma, A.; Legac, J.; Rosenthal, P. J.; Singh, P.; Kumar, V. A trio of quinoline-isoniazid-phthalimide with promising antiplasmodial potential: Synthesis, in-vitro evaluation and heme-polymerization inhibition studies. Bioorg. Med. Chem. 2021, 39, 116159.

[8]. Gentile, D.; Fuochi, V.; Rescifina, A.; Furneri, P. M. New anti SARS-CoV-2 targets for quinoline derivatives chloroquine and hydroxychloroquine. Int. J. Mol. Sci. 2020, 21, 5856.

[9]. Aygün, B.; Alaylar, B.; Turhan, K.; Şakar, E.; Karadayı, M.; Al-Sayyed, M. I. A.; Pelit, E.; Güllüce, M.; Karabulut, A.; Turgut, Z.; Alım, B. Investigation of neutron and gamma radiation protective characteristics of synthesized quinoline derivatives. Int. J. Radiat. Biol. 2020, 96, 1423-1434.

[10]. Almansour, A. I.; Arumugam, N.; Prasad, S.; Kumar, R. S.; Alsalhi, M. S.; Alkaltham, M. F.; Al-Tamimi, H. B. A. Investigation of the optical properties of a novel class of quinoline derivatives and their random laser properties using ZnO nanoparticles. Molecules 2021, 27, 145.

[11]. Harms, K.; Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.

[12]. Farrugia, L. J. WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 2012, 45, 849-854.

[13]. Sheldrick, G. M. A short history ofSHELX. Acta Crystallogr. A 2008, 64, 112-122.

[14]. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. C Struct. Chem. 2015, 71, 3-8.

[15]. North, A. C. T.; Phillips, D. C.; Mathews, F. S. A semi-empirical method of absorption correction. Acta Crystallogr. A 1968, 24, 351-359.

[16]. Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.

[17]. Zhang, C. L.; Qian, J. L.; Zhou, T.; Li, Y. Q. Construction of a cobalt coordination polymer based on a linear ligand with flexible branched chains. J. Struct. Chem. 2021, 62, 918-927.

[18]. Gautam, A.; Shahini, C. R.; Siddappa, A. P.; Jan Grzegorz, M.; Hemavathi, B.; Ahipa, T. N.; Srinivasa, B. Palladium(II) complexes of coumarin substituted 1,2,4-triazol-5-ylidenes for catalytic C-C cross-coupling and C-H activation reactions. J. Organomet. Chem. 2021, 934, 121540.

[19]. 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.

[20]. Diyali, N.; Chettri, M.; De, A.; Biswas, B. Synthesis, crystal structure, and antidiabetic property of hydrazine functionalized Schiff base: 1,2-Di(benzylidene)hydrazine. Eur. J. Chem. 2022, 13, 234-240.

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