Microwave synthesis of some N-phenylhydrazine-1-carbothioamide Schiff bases European Journal of Chemistry 9 (2) (2018) 74-78 European Journal of Chemistry View Journal Online View Article Online Microwave synthesis of some N-phenylhydrazine-1-carbothioamide Schiff bases Bushra Kamil Al-Salami Chemistry Department, College of Science, Basrah University, Basrah, 61001, Iraq bkalsalami62@gmail.com (B.K.A.) * Corresponding author at: Chemistry Department, College of Science, Basrah University, Basrah, 61001, Iraq. Tel: +964.771.4921890 Fax: +964.771.4921890 e-mail: bkalsalami62@gmail.com (B.K. Al-Salami). 10.5155/eurjchem.9.2.74-78.1673 Received: 21 November 2017 Received in revised form: 21 March 2018 Accepted: 21 March 2018 Published online: 30 June 2018 Printed: 30 June 2018 We have synthesized and characterized a series of carbothioamide derivatived molecules, obtained by reaction of aromatic aldehyde (Anisaldehyde, 9-anthraldehyde, cinnamaldehyde, indole-3-carboxaldehyde, 1-naphthaldehyde and o-vanillin) with an equimolar amount of 4- phenylthiosemicarbazide with microwave irradiation. The synthesized compounds have been characterized by FT-IR, 1H NMR and 13C NMR spectroscopy. Quantum calculations of the physical properties, based on density functional theory method at B3LYP/6-31+G(d,p) level of theory, were performed, by means of the Gaussian 09W set of programs. The theoretical 1H NMR chemical shift results of the studied compounds have been calculated at B3LYP method and standard 6-31+G(d,p) basis set using the standard Gauge-Independent Atomic Orbital approach. The calculated values are also compared with the experimental data available for these molecules. A good linear relationship between the experimental and calculated data has been obtained. Synthesis Schiff bases Computational study Microwave irradiation 4-Phenylthiosemicarbazide Carbothioamide derivatives Cite this: Eur. J. Chem. 2018, 9(2), 74-78 Journal website: www.eurjchem.com 1. Introduction Thiosemicarbazide and their Schiff bases have been extensively investigated due to their wide range of application including antibacterial and anticorrosion activities [1-4]. Schiff bases are important intermediates for the synthesis of many bioactive compounds such as β-lactams and thizolodone [2]. They have been prepared by various methods [5], one of the most popular one is by refluxing in a protic solvent a mixture of aldehydes or ketones with primary amines aldehydes. Some cases the reaction need long reaction time and in most cases a catalyst required. During the last decade, the microwave promoted organic synthesis has been used either in especial microwave oven or in domestic ovens, in these ovens despite the power level which commonly fluctuates as a result of the on-off cycles and heterogeneous energy [6]. We selected 4- phenyl-3-thiosemicarbazide as a working compound which is used as pesticide and antibacterial agent [1]. In this study, as part of our research program, we report herein an efficient synthesis of some new functionalized Schiff bases derived from 4-phenyl-3-thiosemicarbazones. In addition, quantum calculations of the physical properties, based on density functional theory method at B3LYP/6-31+G(d,p) level of theory, were performed for the prepared molecules, by means of the Gaussian 09W set of programs. 2. Experimental 2.1. Materials 4-Phenylthiosemicarbazide was purchased from Sigma Chemical Company. o-Vanillin and cinnamaldehyde were purchased from Fluka Chem. Company. Anisaldehyde, 9- anthraldehyde and 1-naphthaldehyde were purchased from BDH Chem. Company. Indol-3-caboxaldehyde was purchased from Himedia Chem. Company. All solvents used were of analytical grade commercially available and used without further purification. 2.2. Instrumentations Microwave irradiation was carried out in a Kenwood microwave oven, model MW303, operating at 800 W. Melting points were recorded on Thermo Fisher Scientific apparatus. FT-IR spectra were recorded as KBr pellets on Shimadzu Inst. in the range from 400-4000 cm-1. ABSTRACT RESEARCH ARTICLE KEYWORDS European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2018 The Authors – Atlanta Publishing House LLC – Printed in the USA. This work is published and licensed by Atlanta Publishing House LLC – CC BY NC – Some Rights Reserved. http://dx.doi.org/10.5155/eurjchem.9.2.74-78.1673 http://dx.doi.org/10.5155/eurjchem.9.2.74-78.1673 https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.9.2.74-78.1673&domain=pdf&date_stamp=2018-06-30 http://www.eurjchem.com/ http://dx.doi.org/10.5155/eurjchem.9.2.74-78.1673 mailto:bkalsalami62@gmail.com mailto:bkalsalami62@gmail.com http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.9.2.74-78.1673&domain=pdf&date_stamp=2018-06-30� Al-Salami / European Journal of Chemistry 9 (2) (2018) 74-78 75 NH3N H S N H Ar-CHO Ar H C N N H S N H MW irradiation Ar : OCH3 N H OCH3 OH 1 2 3 4 5 6 Scheme 1 1H- and 13C-NMR spectra were recorded on Bruker 400 (400 MHz for 1H and 100 MHz for 13C) using CDCl3 or DMSO-d6 as a solvent, TMS as internal reference. 2.3. Synthesis General procedure: A mixture of 4-phenylthiosemicar- bazide (2 mmol) and aromatic aldehyde (Anisaldehyde, 9- anthraldehyde, cinnamaldehyde, indole-3-carboxaldehyde, 1- naphthaldehyde or o-vanillin; 2 mmol) in a flask was inputted into microwave oven and irradiated for 2-15 min. The progress of the reactions were monitored by TLC using hexane:ethylacetate solvent mixture (7:3, v:v). The obtained crude product was recrystallized from suitable solvent (Scheme 1). 2-(4-Methoxybenziylidene)-N-phenylhydrazine-1-carbothio- amide (1): Time: 2 min. Power: 100%. Recryst. solvent: Methanol. Color: Yellow. Yield: 73%. Rf: 0.62. M.p.: 167-169 °C. FT-IR (KBr, ν, cm-1): 3416 (Ph-NH), 3279 (NH), 1204 (C=S). 1H NMR (400 MHz, CDCl3, δ, ppm): 3.90 (s, 3H, OCH3), 6.98-7.82 (m, 9H, Ar-H), 8.63 (1H, HC=N), 11.91 (s, 1H, N-NH). 13C NMR (100 MHz, CDCl3, δ, ppm): 55.35 (OCH3), 114.00-130.01 (Ar-C), 161.03 (Azomethine carbon), 175.18 (C=S). Anal. calcd. for C15H15N3OS: C, 63.13; H, 5.30; N, 14.73. Found: C, 63.41; H, 5.18; N, 15.11%. 2-(Anthracen-9-ylmthylene)-N-phenylhydrazinecarbothio- amide (2): Time: 12 min. Power: 100%. Recryst. solvent: Acetonitrile. Color: Orange. Yield: 81%. Rf: 0.48. M.p.: 201-202 °C. FT-IR (KBr, ν, cm-1): 3274 (NH), 1205 (C=S). 1H NMR (400 MHz, DMSO-d6, δ, ppm): 7.25-8.86 (m, 14H, Ar-H), 9.07 (s, 1H, HC=N), 10.19 (s, 1H, Ph-NH), 11.94 (s, 1H, N-NH). 13C NMR (100 MHz, DMSO-d6, δ, ppm): 123.00-150.02 (Ar-C), 161.26 (Azomethine carbon), 176.40 (C=S). Anal. calcd. for C22H17N3S: C, 74.34; H, 4.84; N, 11.82. Found: C, 74.82; H, 4.97; N, 11.63%. N-Phenyl-2-(3-phenylallylidene)hydrazine-1-carbothioami- de (3): Time: 4 min. Power: 50%. Recryst. solvent: Ethanol. Color: Pale-yellow. Yield: 78%. Rf: 0.58. M.p.: 172-174 °C. FT-IR (KBr, ν, cm-1): 3269 (N-H), 1624 (C=N), 1205 (C=S). 1H NMR (400 MHz, CDCl3, δ, ppm): 6.86 (dd, 1H, C=C-Ha), 6.94 (dd, 1H, Ph-C-Hb), 7.20-7.70 (m, 10H, Ar-H), 7.75 (d, 1H, HC=N), 9.17 (br, 1H, N-NH), 9.75 (s, 1H, Ph-NH). 13C NMR (100 MHz, CDCl3, δ, ppm): 175.38 (C=S), 144.61 (HC=N), 124.00-140.90 (Ar-C), 126.0, 135.6 (CH=CH). Anal. calcd. for C16H15N3S: C, 68.30; H, 5.37; N, 14.93. Found: C, 68.81; H, 5.22; N, 14.78%. 2-((1H-Indol-3-yl)methylene)-N-phenylhydrazine-1-carbo- thioamide (4): Time: 8 min. Power: 100%. Recryst. solvent: Ethanol. Color: Pale-yellow. Yield: 62%. Rf: 0.41. M.p.: 259-261 °C. FT-IR (KBr, ν, cm-1): 3377, 3308 (N-H), 3246 (NH indole), 1614 (C=N), 1246 (C=S). 1H NMR (400 MHz, DMSO-d6, δ, ppm): 7.20-8.88 (m, 10H, Ar-H), 8.41(s, 1H, HC=N), 9.61 (s, 1H, N- NH), 11.58 (s, 1H, Ph-NH), 11.68 (s, 1H, NH indole). 13C NMR (100 MHz, DMSO-d6, δ, ppm): 111.00-141.00 (Ar-C), 165.01 (Azomethine carbon), 174.80 (C=S). Anal. calcd. for C16H14N4: C, 65.28; H, 4.79; N, 19.03. Found: C, 65.41; H, 4.91; N, 19.41%. 2-(Naphthalene-1-ylmethylene)-N-phenylhydrazinecarbo- thioamide (5): Time: 5 min. Power: 100%. Recryst. solvent: Methanol. Color: Orange. Yield: 63%. Rf: 0.43. M.p.: 198-200 °C. FT-IR (KBr, ν, cm-1): 3217 (N-H), 1611 (C=N), 1238 (C=S). 1H NMR (400 MHz, DMSO-d6, δ, ppm): 7.20-8.87 (m, 12H, Ar-H), 9.10 (s, 1H, HC=N), 10.20 (1H, Ph-NH), 11.98 (s, 1H, CS-NH). 13C NMR (100 MHz, DMSO-d6, δ, ppm): 121.01-144.01 (Ar-C), 160.05 (Azomethine carbon), 175.80 (C=S). Anal. calcd. for C18H15N3S: C, 70.79; H, 4.95; N, 13.76. Found: C, 70.22; H, 5.01; N, 13.81%. 2-(2-Hydroxy-3-methoxybenzylidene)-N-phenylhydrazine-1- carbothioamide (6): Time: 2 min. Power: 70%. Recryst. solvent: Ethanol. Color: Pale-yellow. Yield: 73%. Rf: 0.68. M.p.: 205-207 °C. FT-IR (KBr, ν, cm-1): 3337 (OH), 3302 (N-H), 1595 (C=N), 1543 (NH), 1211 (C=S), 1066 (C-O). 1H NMR (400 MHz, CDCl3, δ, ppm): 3.96 (s, 3H, OCH3), 6.94-7.69 (m, 8H, Ar-H), 8.16 (s, 1H, HC=N), 9.53 (s, 1H, Ph-NH), 11.54 (s, 1H, N-NH), 13.21 (s, 1H, OH). 13C NMR (100 MHz, CDCl3, δ, ppm):56.10 (OCH3), 121.00-150.20 (Ar-C), 156.10 (Azomethine carbon), 176.00 (C=S). Anal. calcd. for C15H15N3O2S: C, 59.78; H, 5.02; N, 13.94. Found: C, 59.63; H, 5.13; N, 14.02%. 2.4. Computational study All computational studies were performed with the Gaussian 09W program [7]. Density functional theory (DFT) with B3LYP method was used in present work to perform theoretical calculations on the studied compounds. The geometry of all prepared compounds was optimized at the B3LYP level of theory along with standard 6-31+G(d,p) basis set. The electronic properties were calculated using B3LYP/6- 31+G(d,p) based on the optimized structures [8-10]. Mulliken atomic charges have been calculated in same level of theory. Also, the theoretical 1H NMR chemical shift have been calculated at B3LYP method and standard 6-31+G(d,p) basis set using the standard GIAO (Gauge-Independent Atomic Orbital) approach. The magnetic shielding tensor of the protons of the studied compounds has been determined. 3. Results and discussion 3.1. Synthesis The preparation and purification procedures are simple and it gives good yields within a few minutes. The synthesized compounds are crystalline solids stable in air, most of them soluble in DMF and DMSO and sparingly soluble in methanol, ethanol, hexane, acetonitrile and benzene. The proposed molecular formulas for prepared compounds are in agreement with analytical data (C, H and N) together with spectroscopic data namely IR, 1H NMR and 13C NMR. 2018 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.9.2.74-78.1673 76 Al-Salami / European Journal of Chemistry 9 (2) (2018) 74-78 Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 Compound 6 Figure 1. The optimized structure of compounds 1-6 within numbering of atoms. The IR spectra provide valuable information regarding the formation of Schiff bases. All compounds show a strong bands at 1640 to 1611 cm-1 attributed azomethine (-C=N-)stretching vibration also all compounds shows a bands at 1267-1264 cm- 1 and at 3217 and 3377 cm-1which attributed to C=S and NH stretching vibration, respectively. The totally absence of SH stretching vibration together with strong band of C=S gives good evidence that these compounds existed in thione-amine form. The 1H NMR and 13C NMR data of compounds recorded at room temperature in DMSO-d6 or CDCl3. The NH signal in all compounds is solvent dependent where appear down field in DMSO-d6 compared with CDCl3. All the other signals appear at expected region. The 1H NMR spectrum of compound 1 in CDCl3 showed two singlet signals for methoxy protons at δ 3.90 ppm and for azomethine proton at δ 8.63 ppm along with multiplet in the region δ 6.98-7.82 ppm for aromatic protons. The 1H NMR spectrum of compound 3 in CDCl3 showed two doublets of doublet signals for olefinic protons at δ 6.86 and 6.94 ppm. The azomethine proton signal appears at 7.75 ppm.13C NMR spectrum of compound 3 showed a signals at δ 175.38 ppm attributed to C=S, 144.61 ppm for azomethine carbon. 1H NMR spectrum of compound 4 (in DMSO-d6) showed five signals at 11.68 ppm as abroad band attributed to NH of indole moiety [11]. Singlet at δ 11.58 for Ph-NH, singlet at 9.61 ppm N-NH, singlet at δ 8.41 ppm for azomethine proton and multiplet in the region δ 7.20-8.88 ppm attributed to aromatic protons. 3.2. Computational study Theoretical investigations were performed using the Density Functional Theory at B3LYP level of theory at 6- 31+G(d,p) in the Gaussian 09W program. The optimized structure of compound 1 with labeling of atoms is given in Figure 1 as an example. Figure 1 shows the compound in the ball and stick model. 3.2.1. Mulliken population analysis Dipole moment, molecular polarizability and bond properties are affected by atomic charges, therefore, the Mulliken atomic charge calculation has an important role [11- 13]. 2018 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.9.2.74-78.1673 Al-Salami / European Journal of Chemistry 9 (2) (2018) 74-78 77 Table 1. The Mulliken atomic charge (a.u.) distribution of some atoms of the synthesized compounds. Atoms Compound 1 2 3 4 5 6 1C 0.0157 0.0109 0.1390 -0.5600 0.0281 -0.3150 2C 0.0075 -0.0104 -0.0355 0.0980 -0.0158 0.0559 3C -0.1200 -0.1164 -0.0872 -0.1500 -0.1095 -0.0620 4C -0.4895 -0.5747 -0.4400 0.0510 -0.5258 0.2665 5C 0.1562 0.1357 0.1429 -0.6990 0.1934 -0.7610 6C 0.5746 0.7094 0.4152 1.1540 0.6018 0.7539 7N 0.0349 0.0432 0.0255 0.1840 0.0265 0.0558 8C -0.1715 -0.2227 -0.1727 -0.2810 -0.2018 0.1004 9S -0.0298 -0.0492 -0.0778 0.0980 -0.0390 -0.1530 10N -0.1740 0.0693 0.1115 0.0710 -0.0838 0.1180 11N 0.3709 0.1460 -0.0219 -0.0040 0.3031 0.0696 12C 0.1593 -0.2352 -0.4941 -0.4910 0.0305 0.3305 13C 0.3539 0.2050 0.0761 0.8430 0.2070 0.5146 14C 0.3924 0.4929 0.0481 0.1860 -0.4809 0.9277 20 H 0.1246 0.1497 0.1144 0.1387 0.1226 0.1597 Figure 2. The Mulliken atomic charge distribution of some atoms of the synthesized compounds. Figure 3. Experimental values vs. theoretical 1H NMR chemical shifts for azomethine proton of studied molecules. Mulliken population analysis was performed at the same level of theory. Illustration of atomic charges plotted for some atoms of studied compound obtained by Mulliken population is shown in Figure 2. As can be seen in Table 1, all the hydrogen atoms have a net positive charge. The obtained atomic charge shows that 20 H atom of compound 6 has bigger positive atomic charge (0.1597) than the other same hydrogen atoms in the studied compound. The C12 atom of compound 3 has bigger negative atomic charge (-0.4941) than the other same carbon atoms in the studied compound and C5 atom of compound 6 (-0.7610). 3.2.2. NMR analysis The NMR calculations are widely use to complement experimental measurements to solve structural problems [14]. The theoretical 1H NMR chemical shift results of the studied compounds have been calculated at B3LYP methods and standard 6-31+G(d,p) basis set using the standard GIAO (Gauge-Independent Atomic Orbital) approach. The calculated values are compared with the experimental data available for these molecules. A good linear relationship between the experimental and calculated data has been obtained shown in Figure 3. The magnetic shielding tensor can be used as a probe of intermolecular structure. The magnetic nucleus becomes a sensitive probe of the local electron distribution, providing information about molecular structure. Moreover, the shielding tensor is affected when a molecule is brought from an ideal gas into a condensed phase [15]. The magnetic shielding tensor of the studied compounds has been determined using DFT at B3LYP methods and standard 6- 31+G(d,p) basis set using the standard GIAO approach (Table 2). 2018 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.9.2.74-78.1673 78 Al-Salami / European Journal of Chemistry 9 (2) (2018) 74-78 Table 2. Experimental, theoretical chemical shifts and calculated 1H shielding with B3LYP/6-31+G(d,p)/ GIAO approach for azomethine proton of studied molecules. Compounds Chemical shielding azomethine proton 1H Chemical shift Isotropic Anisotropic Experimental Calculated 1 23.1259 7.6718 8.63 8.86 2 22.3670 10.9716 9.07 9.03 3 24.4444 5.4940 7.75 7.68 4 23.8280 8.6557 8.41 8.33 5 22.8982 10.7818 9.10 8.98 6 24.2332 11.7370 8.16 8.32 4. Conclusions We have synthesized and characterized six carbothio- amide derivatives (2-(4-methoxybenziylidene)-N-phenyl- hydrazine-1-carbothioamide, 2-(anthracen-9-ylmthylene)-N- phenylhydrazinecarbothioamide, N-phenyl-2-(3-phenylallyli- dene)hydrazine-1-carbothioamide, 2-((1H-indol-3-yl)methyle- ne)-N-phenylhydrazine-1-carbothioamide, 2-(naphthalene-1- ylmethylene)-N-phenylhydrazine carbothioamide and 2-(2- hydroxy-3-methoxybenzylidene)-N-phenyl hydrazine-1-carbo- thioamide). The prepared compounds primarily investigated by performing density functional theory calculations. The theoretical 1H NMR chemical shift results of the studied compounds have been calculated at B3LYP methods and standard 6-31+G(d,p) basis set using the standard Gauge- Independent Atomic Orbital approach. The calculated values are also compared with the experimental data available for these molecules. A good linear relationship between the experimental and calculated data has been obtained. Acknowledgements The author thanks The Central Laboratory of Esfahan University for financial support for NMR and CHNS analysis, also the author thank Dr. Adil Mualla Dhumad from University of Basrah for her helpful the discussion of the theoretical part of this article. Disclosure statement Conflict of interests: The author declares that she has no conflict of interest. Ethical approval: All ethical guidelines have been adhered. Sample availability: Samples of the compounds are available from the author. Funding University of Basrah http://dx.doi.org/10.13039/100012026 ORCID Bushra Kamil Al-Salami http://orcid.org/0000-0002-6023-3071 References [1]. Ebrahimi, H. P.; Hadi, J. S.; Alsalim, T. A.; Ghali, T. S.; Bolandnazer, Z. Spect. Chim. Acta A 2015, 137, 1067-1077. [2]. Ebrahimi, H. P.; Hadi, J. S.; Almayah, A. A.; Bolandnazar, Z.; Swadi, A. G.; Ebrahimi, A. P. Bioorg. Med. Chem. 2016, 24, 1121-1131. [3]. Singh, M. M.; Rastogi, R. B.; Upadhyay, B. N.; Yadav, M. Mater. Chem. Phys. 2003, 80, 283-293. [4]. Al-Salami, B. K.; Mohammed, A. H.; Askar, K. A, Res. J. Pharm. Bio. Chem. 2014, 5(4), 1457-1472. [5]. Patai, S. The Chemistry of Carbon-Nitrogen Double Bond, John Wiley & Sons Ltd., 1970. [6]. Loupy, A. Microwaves In Organic Synthesis, Wiley-VCH, Weinheim, 2002. [7]. Frisch, M. J.; Trucks G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. 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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). 2018 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.9.2.74-78.1673 http://dx.doi.org/10.13039/100012026 http://orcid.org/0000-0002-6023-3071 http://www.eurjchem.com/index.php/eurjchem/pages/view/terms http://creativecommons.org/licenses/by-nc/4.0 http://www.eurjchem.com/index.php/eurjchem/pages/view/terms 1. Introduction 2. Experimental 2.1. Materials 2.2. Instrumentations 2.3. Synthesis 2.4. Computational study 3. Results and discussion 3.1. Synthesis 3.2. Computational study 3.2.1. Mulliken population analysis 3.2.2. NMR analysis 4. Conclusions Acknowledgements Funding ORCID References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: