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        Synthesis and X-ray diffraction crystallographic characterization of compound 2-(α-naphtyl)-3-(α-pyridinyl)-1,3-thiazolidin-4-one
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        Synthesis and X-ray diffraction crystallographic characterization of compound 2-(α-naphtyl)-3-(α-pyridinyl)-1,3-thiazolidin-4-one
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        Synthesis and X-ray diffraction crystallographic characterization of compound 2-(α-naphtyl)-3-(α-pyridinyl)-1,3-thiazolidin-4-one
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Abstract

Thiazolidinones present a wide range of useful applications especially in the biological aspect. Based on these facts, the compound of interest 2-(α-naphthyl)-3-(α-pyridinyl)-1,3-thiazolidine-4-one (C18H14N2OS), was synthesized via multi-component reaction with the aim of obtaining a compound that would show activity against fungi and bacteria. The synthesis of 2-(α-naphthyl)-3-(α-pyridinyl)-1,3-thiazolidine-4-one, was carried out from the respective α-aminopyridine with α-naphthylaldehyde and α-mercaptoacetic acid, under reflux in dry toluene for 8 h, obtaining a solid compound. Molecular characterization of the compound was carried out by infrared spectrometry, mass spectrometry, and nuclear magnetic resonance. The study of the crystallization and the calculation of the unit-cell constants were determined by the technique of X-ray diffraction of polycrystalline samples. It was determined that the compound crystallizes in a monoclinic system with space group P21/c [No. 14] and the constants of the unit cell a = 11.958 (3), b = 9.675 (4), c = 12.661 (4) Å, β = 96.960° (2), V = 1454.01 (Å3).

I. INTRODUCTION

Five member heterocyclic compounds are known for their multiple applications which have motive their wide study. Among this group of heterocycles, thiazolidinones have performed a wide range of biological activity (antifungal, antibacterial, analgesic, pesticide, herbicide, antitubercular, local anesthetic, and antimicotic) (Brown, 1961; Singh, 2014). The biological meaning of this class of compounds stimulates the study upon the synthesis and properties of our compound of interest 2-(α-naphtyl)-3-(α-pyridinyl)-1,3-thiazolidin-4-one, because several protocols have been developed for the synthesis of these kind of materials (Kouznetsov et al., 2006; Pȃnzariu et al., 2016). Thiazolidinone of interest was synthesized via multicomponent reaction in order to obtain a new compound with prominent antifungal and antibacterial activity.

II. EXPERIMENTAL

A. Synthesis

Compound 2-(α-naphtyl)-3-(α-pyridinyl)-1,3-thiazolidin-4-one (4) was synthesized by means of a multicomponent reaction promoted by glacial acetic acid in stoichiometric quantities between α-aminopyridine (1), α-naphtylaldehyde (2), and α-mercaptoacetic acid (3), employing anhydride toluene as solvent to reflux for 8 h. The preparation route of the interest compound is shown in Figure 1.

Figure 1. Synthesis of 2-(α-naphtyl)-3-(α-pyridinyl)-1,3-thiazolidin-4-one via multicomponent reaction.

Once the synthesis process was accomplished, the melting point (measured on a Fisher Johns melting point apparatus) and density (by floating method) were determined, and the molecular characterization of the compound was developed through instrumental methods of infrared spectrometry (IR) employing a Lumex Infralum FT-02 (KBr) spectrophotometer, gas chromatography coupled to mass spectrometry (GC–MS) using a gas chromatograph Agilent Technologies 6890 with an interface to a mass selective detector Agilent Technologies MSD 5963, and nuclear magnetic resonance (NMR) with a Bruker AM-400 or AC-300.

B. Powder data collection

A small amount of the compound, C18H14N2OS was gently ground in an agate mortar and sieved to a grain size of <38 µm. The specimen was mounted on a zero-background specimen holder (Buhrke et al., 1998) for the respective measurement. The data were collected at 298 K using a Rigaku model D/MAX IIIB diffractometer with a graphite monochromator operating in Bragg–Brentano geometry equipped with an X-ray tube (CuKα radiation: λ = 1.5406 Å, 40 kV and 35 mA), a NaI (Tl) scintillation detector, and fixed scatter and divergence slits of 1° and 0.03 mm receiving slit. The scan range was from 2 to 70° 2θ with a step size of 0.02° 2θ and a counting time of 15 s step−1.

POWDERX program (Dong, 1999) was used to remove the background (Sonneveld and Visser, 1975), smooth the data (Savitzky and Golay, 1964), eliminate the Kα 2 component (Rachinger, 1948), and to determine the positions and intensities of the diffraction peaks, using the second derivative method.

III. RESULTS AND DISCUSSION

A. Synthesis

Compound 2-(α-naphtyl)-3-(α-pyridinyl)-1,3-thiazolidin-4-one was obtained with a 62% yield, with a melting point of 141–143 °C, and a measured density of 1.32 g cm−3. Molecular characterization of the compound was developed by IR spectrometry: tension C(sp 3)–H (3054.74); tension C(sp 2)–H (3000.75); vibration tension C(=O)–N (1689.37); vibration tension C(sp 2)–C (1581.37); enlargement C–N (1432.22); asymmetric tension C(sp 2)–O (1288.24); deformation vibration C(sp 2)–H (779.11), deformation vibration C–S (685.33); GC–MS: m/z = 306.38 (M+) and NMR: 1H NMR (400 MHz, CDCl3) δ (ppm) 8.39 (1H, d, J = 8.4 Hz, 14-H), 8.12 (1H, d, J = 4.1 Hz, 4-H), 8.05 (1H, d, J = 8.4 Hz, 12-H), 7.89 (1H, d, J = 8.0 Hz, 10-H), 7.74 (2H, t, J = 8.4 Hz, 11-H, 13-H), 7.68 (1H, s, 3-H), 7.63 (1H, t, J = 7.6 Hz, 7-H), 7.55 (1H, t, J = 7.4 Hz, 7-H), 7.30 (1H, t, J = 7.7 Hz, 9-H), 7.19 (1H, d, J = 7.1 Hz, 6-H), 6.97 (1H, t, J = 6.0 Hz, 5-H), 3.97 (1H, d, J = 16.1 Hz, 1-H), 3.79 (1H, d, J = 16.1 Hz, 2-H). 13C NMR (101 MHz, DMSO) δ 172.19, 151.04, 147.96, 137.98, 136.19, 134.30, 129.92, 129.24, 128.68, 126.73, 126.19, 125.21, 122.83, 121.00, 120.57, 116.08, 59.84, 34.51.

B. X-ray diffraction of polycrystalline samples

The X-ray powder diffraction (XRPD) pattern of 2-(α-naphthyl)-3-(α-pyridinyl)-1,3-thiazolidine-4-one is shown in Figure 2; a small amount of amorphous component in the background was observed because of the type of mount since paraffin was used as a support, which results in some discrepancies in peak intensities of the reflection list, compared with the simulated pattern, using a Le Bail refinement. The peak list for this compound are given in Table I. The XRPD pattern was successfully indexed using the DICVOL06 program (Boultif and Louër, 2006) on a monoclinic cell with an absolute error of ±0.03°2θ in the calculations. The space group, P21/c [No. 14] was estimated by the CHEKCELL program (Laugier and Bochu, 2002), which was compatible with the systematic absences and the crystal density, 1.320 g cm−3. The unit-cell parameters were refined with the NBS*AIDS83 program using the total observed reflex ions (Miguell et al., 1981). The crystal data, X-ray density, as well as figures of merit M 20 (de Wolff, 1968) and F 30 (Smith and Snyder, 1979) are compiled in Table II.

Figure 2. X-ray powder diffraction pattern of 2-(α-naphtyl)-3-(α-pyridinyl)-1,3-thiazolidin-4-one.

Table I. X-Ray diffraction data for the compound 2-(α-naphtyl)-3-(α-pyridinyl)-1,3-thiazolidin-4-one.

Table II. Crystal data for 2-(α-naphtyl)-3-(α-pyridinyl)-1,3-thiazolidin-4-one via multicomponent reaction.

SUPPLEMENTARY MATERIAL

The supplementary material for this article can be found at https://doi.org/10.1017/S0885715618000453

ACKNOWLEDGEMENTS

This work was supported by grant 1102-05-17590 Colciencias (Patrimonio Autónomo del Fondo Nacional de Financiamiento para la Ciencia, la Tecnología y la Innovación, Francisco José de Caldas).

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