untitled European Journal of Chemistry 8 (1) (2017) 18‐19 European Journal of Chemistry ISSN 2153‐2249 (Print) / ISSN 2153‐2257 (Online)  2017 Atlanta Publishing House LLC ‐ All rights reserved ‐ Printed in the USA http://dx.doi.org/10.5155/eurjchem.8.1.18-19.1510 European Journal of Chemistry Journal webpage: www.eurjchem.com Synthesis and characterization of 1,3‐bis(2‐fluorophenyl)‐5‐pentyl‐1,3,5‐triazinane Amel Ferhati *, Achene Bouchemma, Mustapha Bouhenguel, Leila Lefrada and Assia Sid Laboratory of Applied Chemistry and Materials Technology, Faculty of Exact Sciences and Natural Sciences and life, Department of Material Sciences, Larbi Ben M’hidi University, Oum El Bouaghi, 04000, Algeria * Corresponding author at: Laboratory of Applied Chemistry and Materials Technology, Faculty of Exact Sciences and Natural Sciences and life, Department of Material Sciences, Larbi Ben M’hidi University, Oum El Bouaghi, 04000, Algeria. Tel.: +213.32686287. Fax: +213.32424213. E‐mail address: ferhatiamel@gmail.com (A. Ferhati). ARTICLE INFORMATION ABSTRACT DOI: 10.5155/eurjchem.8.1.18-19.1510 Received: 14 November 2016 Received in revised form: 14 January 2017 Accepted: 14 January 2017 Published online: 31 March 2017 Printed: 31 March 2017   A new triazinane derivative was obtained by condensation reaction of pentylamine, 2‐ fluoroaniline and formaldehyde (formalin) in basic solution to yield 1,3‐bis(2‐fluorophenyl)‐ 5‐pentyl‐1,3,5‐triazinane. The structure of the synthesized compound was characterized by spectroscopic methods: FT‐IR, UV‐Vis, 13C, 19F and 1H NMR. KEYWORDS Triazinane Pentylamine Formaldehyde 2‐Fluoroaniline IR spectroscopy Heterocyclic nitrogen compound Cite this: Eur. J. Chem. 2017, 8(1), 18‐19 1. Introduction Triazacyclohexanes, as heterocyclic nitrogen compounds, have been proved to play crucial roles in several fields. They represent an important class in coordination chemistry [1]. They are used a framework for conformational studies in structural chemistry [2,3]. Theoretical studies using density functional theory (DFT) at B3LYP/6‐31++G (d.p) were carried out on five various sym‐ 1,3,5‐triaryl‐1,3,5‐triazacyclohexanes utilized as a corrosion inhibitors mild steel in acidic medium [4] and in organometallic as ligands in preparation of various complexes [5] which can be used as catalyst in the trimerisation and polymerization reactions [6]. The triazacyclohexane was synthesized via condensation reaction between primary amines (arylamine and alkylamine) and formaldehyde (formalin) in basic solution (in aqueous solution of potassium hydroxide) [7,8]. In this study, triazacyclohexane was synthesized from condensation reaction with primary amines and formaldehyde (formalin) in basic solution [8,9]. 2. Experimental 2.1. Instrumentation Melting point was determined on a capillary melting point apparatus. Analytical thin layer chromatography (TLC) was conducted on percolated TLC plates (silicagel 60F254, Merck) visualized under UV light and stained with dichloromethane as an eluent. 1H (300 MHz), 13C (75 MHz) and 19F NMR (376 MHz) spectra were recorded on a Bruker spectrometer in CDCl3 (internal standard and TMS, δ = 0.0 ppm) at room temperature. IR spectra were recorded in KBr pellet on Shimadzu FT‐IR 8201 PC (4000‐400 cm‐1). 2.2. Synthesis A mixture of 2‐fluoroaniline and pentylamine (2:1, v:v) ratio were stirred overnight at ambient temperature with water (10 cm3), potassium hydroxide (1.18 g, 30 mmol) and an excess of formalin (6 mL). The resulting oily phase was extracted with CH2Cl2, dried with MgSO4 and evaporated to dryness [3]. The product was solidified on standing after 2 days [7]. Recrystallization from dichloromethane affords the triazacyclohexane derivative as needles in a high yield. Ferhati et al. / European Journal of Chemistry 8 (1) (2017) 18‐19 19 Scheme 1 1,3‐Bis(2‐fluorophenyl)‐5‐pentyl‐1,3,5‐triazinane: Color: Colorless. Yield: 90%. M.p.: 123‐125 °C. FT‐IR (KBr, ν, cm‐1): 3087 (Ar‐H), 2958‐2871 (CH3, CH2), 1598, 1496 (C=C), 1461 (CH2), 1376 (CH3), 1201 (C‐F), 754 (Ar‐H). 1H NMR (300 MHz, CDCl3, δ, ppm): 0.88 (t, 3H, CH3), 1.51 (m, 6H, CH2), 2.58 (m, 2H, CH2), 4.28 (s, 4H, C5H11‐N‐CH2‐N‐Ar), 4.73 (s, 2H, Ar‐N‐ CH2‐N‐Ar), 6.86‐7.28 (m, 8H, Ar‐H). 13C NMR (75 MHz, CDCl3, δ, ppm): 11.90 (CH3‐CH2), 20.62 (CH3‐CH2), 54.07 (C4H9‐CH2‐N), 69.58 (C5H11‐N‐CH2‐N‐Ar), 71.23 (Ar‐N‐CH2‐N‐Ar), 115.30 (C, Ar‐H), 120.07 (C, Ar‐F), 122.65 (C, Ar‐H). 19F NMR (376.46 MHz, CDCl3, δ, ppm): ‐125.042, ‐135.617 (C‐F). UV/Vis (CHCl3, λmax, nm): 238(4). 3. Results and discussion The condensation of 2‐fluoroaniline and pentylamine with formalin afforded an unsymmetrically substituted triazacyclo‐ hexane (Scheme 1) [5,6]. This product is stable at room temperature and obtained in high yield 90%. Recrystallization of the obtained solid product from dichloromethane gave transparent needles. The mechanism of this condensation involves the attack of nucleophilic species with formaldehyde to form an imine which trimerizes to give 1,3,5‐triazacyclo‐ hexane [6,7,9‐11]. The characterization of title compound has been explained by FT‐IR, UV‐Vis, 1H, 13C and 19F NMR. The infrared spectrum reveals a weak stretching band at 3087 cm‐1 of C‐H aryl system, four strong bands at 2958‐2871 cm‐1 due to stretching vibration of asymmetric and symmetric stretching of the C‐H band (CH2 and CH3), at 1598 and 1496 cm‐1 strong bands characterize the stretching band (C=C) of the aromatic system, a strong band at 1461 cm‐1 due to in the plane symmetric deformation of the C‐H band of the methylene group CH2, a medium strong band at 1376 cm‐1 due to symmetric deformation of three C‐H methyl group CH3, a strong sharp band at 1201 cm‐1 resulting from the stretching vibration of C‐ F, in the deformation zone, a strong band at 754 cm‐1 due to out of the plane deformation C‐H aryl system. The 1H NMR spectrum shows protons of the methyl group resonate as triplet at δ 0.88 ppm, the six protons of the three CH2 group adjacent to both ‐CH2‐N‐ and CH3 groups appear as multiplet at δ 1.51 ppm. The multiplet centered at δ 2.58 ppm shows the resonance of the protons of CH2 of the alkyl attached to the nitrogen. The two various pics of methylene group at δ 4.28 ppm (CH2‐N(C5H11)‐CH2) and at δ 4.73 ppm (Ar‐N‐CH2‐N‐Ar) indicate the formation of triazinane derivative. Finally the protons of the aromatic system appear between δ 6.86 and 7.28 ppm. The 13C NMR spectra shows the carbons atoms of pentyl group appear at δ 11.90, 20.62 and 54.07 ppm, the carbon atoms of triazinane cycle appears at δ 69.58 and 71.23 ppm, the carbons of aryl ring which has a flour atoms appear at δ 120.07 ppm, the other carbon atoms of the aryl group appears at δ 115.30 and 122.65 ppm. 4. Conclusion In conclusion, we have synthesized a new triazinane derivative; the synthesized compound was identified by spectral data. This compound can be a useful ligand for the preparation of organometallic complexes. Acknowledgements We gratefully acknowledge Professor Mustapha Bouhenguel Director of the Laboratory of Applied Chemistry and Materials Technology of the University of Oum El Bouaghi for his support of this work. We gratefully acknowledge Mr. Paul Mosset Doctor at the University of Rennes 1, France for providing spectroscopic analysis and we would like to thank Professor Randolf Kohn at University of Bath, England for his help. References [1]. Randolf, D. K.; Matthias, H.; Shahram, M.; Dieter, L. Chem. Commun. 2000, 19, 1927‐1928. [2]. Mahmoud, C.; Amel, M.; Duygu, B.; Ahcen, B.; Cemal, P. J. Mol. Struc. 2017, 1129, 152‐159. [3]. Bouchemma, A.; Peter, H. M.; George, A. S. J. Chem. Soc. Perkin Trans. II 1989, 6, 583‐587. [4]. Dilara, O.; Nihat, K. J. Taiwan Inst. Chem. Eng. 2015, 50, 306‐313. [5]. Saida, L.; Abdelhamid, M.; Gabriele, K. K.; Randolf, D. K.; Frank, S. Polyhedron 2010, 29, 1399‐1404. [6]. Guide, S. 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