European Journal of Chemistry 2019, 10(1), 72-81. doi:10.5155/eurjchem.10.1.72-81.1812

Synthesis, characterization and thermal decomposition of ethyl-2’-amino-5’-cyano-6’-(1H-indole-3yl)-2-oxospiro[indoline-3,4’-pyran]-3’-carboxylate under non‐isothermal condition in nitrogen atmosphere


Ganesan Nalini (1,*) orcid , Natesan Jayachandramani (2) orcid , Radhakrishnan Suresh (3) orcid , Prakasam Thirumurugan (4) orcid , Venugopal Thanikachalam (5) orcid , Govindasamy Manikandan (6) orcid , Dharmalingam Sankari (7) orcid

(1) Department of Biotechnology, Faculty of Science and Humanities, SRM Institute of Science and Technology, Kattankulathur, 603203, India
(2) Department of Chemistry, Pachaiyappa’s College, Chennai, 600030, India
(3) Department of Chemistry, Presidency College, Chennai, 600005, India
(4) Department of Chemistry, New York University, Abu Dhabi, United Arab Emirates
(5) Department of Chemistry, Annamalai University, Annamalainagar, 608002, India
(6) Department of Chemistry, Annamalai University, Annamalainagar, 608002, India
(7) Department of Biotechnology, Faculty of Science and Humanities, SRM Institute of Science and Technology, Kattankulathur, 603203, India
(*) Corresponding Author

Received: 03 Nov 2018, Accepted: 30 Jan 2019, Published: 31 Mar 2019

Abstract


A new compound, spiro-oxindole derivative compound namely ethyl-2ʹ-amino-5ʹ-cyano-6ʹ-(1H-indole-3yl)-2-oxospiro[indoline-3,4ʹ-pyran]-3ʹ-carboxylate (EACIOIPC) has been synthesized and characterized by microanalysis, FT-IR, mass spectrum and NMR (1H and 13C) techniques. The thermal decomposition of the compound was studied by thermogravimetric analysis under dynamic nitrogen atmosphere at different heating rates of 10, 15, 20 and 30 K/min. The kinetic parameters were calculated using model-free (Friedman’s, Kissinger-Akahira-Sunose (KAS) and Flynn-Wall-Ozawa (FWO) methods) and model-fitting (Coats and Redfern (CR)) methods. The decomposition process of EACIOIPC followed a single step mechanism as evidenced from the data. Existence of compensation effect is noticed for the decomposition of EACIOIPC. Invariant kinetic parameters are consistent with the average values obtained by Friedman and KAS in conversional methods.


Keywords


Model fitting; IKP methods; Spiro-oxindole; Model free methods; Thermal decomposition; Thermodynamic parameters

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DOI: 10.5155/eurjchem.10.1.72-81.1812

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References

[1]. Bhaskar, G.; Arun, Y.; Balachandran, C.; Saikumar, C.; Perumal, P. T. Eur. J. Med. Chem. 2012, 51, 79-91.
https://doi.org/10.1016/j.ejmech.2012.02.024

[2]. Gribble, G. W. J. Chem. Soc. Perkin Trans. I 2000, 1045-1075.
https://doi.org/10.1039/a909834h

[3]. Zhu, S. L.; Ji, S. L.; Su, X. M.; Sun, C.; Liu, Y. Tetrahedron Lett. 2008, 49, 1777-1781.
https://doi.org/10.1016/j.tetlet.2008.01.054

[4]. Farghaly, A. M.; Habib, N. S.; Khalil, M. A.; El-Sayed, O. A. Alexandria. J. Pharm. Sci. 1989, 3, 84-86.

[5]. Yu, B.; Yu, D. Q.; Liu, H. M. Eur. J. Med. Chem. 2015, 97, 673‐698.
https://doi.org/10.1016/j.ejmech.2014.06.056

[6]. Fuchao, Y.; Huang, R.; Hangchen, N.; Juan, F.; Shengjiao, Y.; Lin, L. Green. Chem. 2013, 15, 453-462.
https://doi.org/10.1039/C2GC36552A

[7]. Arun, Y.; Bhaskar, G.; Balachandran, C.; Ignacimuthu, S.; Perumal, P. T. Bioorg. Med. Chem. Lett. 2013, 23, 1839-1845.
https://doi.org/10.1016/j.bmcl.2013.01.023

[8]. Georgieva, V.; Zvezdova, D.; Vlaev, L. Chem. Cent. J. 2012, 6, 81, 1-10

[9]. Georgieva, V.; Zvezdova, D.; Vlaev, L. J. Therm. Anal. Calorim. 2013, 111, 763-771.
https://doi.org/10.1007/s10973-012-2359-6

[10]. Fulias, A.; Vlase, G.; Vlase, T.; Soica, C.; Heghes, A.; Craina, M.; Ledeti, I. Chem. Cent. J. 2013, 7, 70, 1-8.

[11]. Fulias, A.; Vlase, G.; Grigorie, C.; Ledeti, I.; Albu, P.; Bilanin, M.; Vlase, T. J. Therm. Anal. Calorim. 2013, 113, 265-271.
https://doi.org/10.1007/s10973-013-2959-9

[12]. Kamel, T. L. Eur. J. Chem. 2015, 6(2), 199-203.
https://doi.org/10.5155/eurjchem.6.2.199-203.1249

[13]. Nalini, G.; Jayachandramani, N.; Thanikachalam, V.; Jayabharathi, J.; Manikandan, G.; Suresh, R. Can. Chem. Trans. 2016, 4, 62-72.

[14]. Nalini, G.; Jayachandramani, N.; Suresh, R.; Thanikachalam, V.; Manikandan, G. Eur. J. Chem. 2016, 7(3), 380-386.
https://doi.org/10.5155/eurjchem.7.3.380-386.1442

[15]. Nalini, G.; Jayachandramani, N.; Suresh, R.; Thirumurugan, P.; Thanikachalam, V.; Manikandan, G. Int. J. Adv. Chem. Sci. App. 2016, 3(4), 25-38.

[16]. Alok, D.; Suraj, B. S.; Muammel, M. H.; Rekha, R. Environ. Clim. Technol. 2018, 22, 5-21.
https://doi.org/10.1515/rtuect-2018-0001

[17]. Venkatesh, M.; Ravi, P.; Surya, P. T. J. Phys. Chem. A 2013, 117, 10162-10169.
https://doi.org/10.1021/jp407526r

[18]. Ashis, B.; Amlan, R.; Debasis, R.; Madhusudan, R. J. Exp. Phys. 2014, Article ID: 513268.

[19]. Nandakumar, A.; Thirumurugan, P.; Perumal, P. T.; Vembu, P.; Ponnuswamy, N. M.; Ramesh, P. Bioorg. Med. Chem. Lett. 2010, 20, 4252-4258.
https://doi.org/10.1016/j.bmcl.2010.05.025

[20]. Coats, A. W.; Redfern, J. P. Nature (London) 1968, 201, 68-69.
https://doi.org/10.1038/201068a0

[21]. Wendlandt, W. W. Thermal Methods of Analysis, John Wiley and Sons Inc., New York, 1974.

[22]. Friedman, H. L. Polym. Sci. 1963, 6, 183-195.

[23]. Flynn, J. H.; Wall, L. A. J. Res. Natl. Bur. Stand. 1966, 70, 487-523.
https://doi.org/10.6028/jres.070A.043

[24]. Ozawa, T. Bull. Chem. Soc. Jpn. 1965, 38, 1881-1886.
https://doi.org/10.1246/bcsj.38.1881

[25]. Kissinger, H. E. Anal. Chem. 1957, 29, 1702-1706.
https://doi.org/10.1021/ac60131a045

[26]. Akahira, T.; Sunose, T. Res. Rep. CHIBA Inst. Technol. 1971, 16, 22-31.

[27]. Lesnikovich, A. I.; Levchik, S. V. J. Therm. Anal. 1985, 30, 237-262.
https://doi.org/10.1007/BF02128134

[28]. Lesnikovich, A. I.; Levchik, S. V. J. Therm. Anal. 1983, 27, 89-94.
https://doi.org/10.1007/BF01907324

[29]. Malek, J. A. Thermochim. Acta 1989, 136, 337-346.
https://doi.org/10.1016/0040-6031(89)87270-3

[30]. Malek, J. Thermochim. Acta 1992, 200, 257-269.
https://doi.org/10.1016/0040-6031(92)85118-F

[31]. Cordes, F. H. J. Phys. Chem. 1968, 72, 2185-2189.
https://doi.org/10.1021/j100852a052

[32]. Bamford, C. H.; Tipper, C. F. H. Comprehensive chemical kinetics, Reactions in the Solid State 1980, 22, 1-340.

[33]. Pratap, A.; Rao, T. L. S.; Dhaurandhar, H. D. J. Therm. Anal. Calorim. 2007, 89, 399-405.
https://doi.org/10.1007/s10973-006-8160-7

[34]. Criado, J. M.; Morales, J. Thermochim. Acta 1976, 16, 382-387
https://doi.org/10.1016/0040-6031(76)80031-7

[35]. Venkatesan, J.; Sekar, M.; Thanikachalam, V.; Manikandan, G. Chemical Data Collections, 2017, 9(10), 67-79.

[36]. Manikandan, G.; Rajarajan, G.; Jayabharathi, J.; Thanikachalam, V. Arab. J. Chem. 2011, 9, 570-575.
https://doi.org/10.1016/j.arabjc.2011.06.029

[37]. Ma, H. X.; Yan, B.; Li, Z. N.; Song, J. R.; Hu, R. Z. J. Therm. Anal. Calorim. 2007, 95, 437-444.
https://doi.org/10.1007/s10973-008-9255-0

[38]. Boonchom, B. J. Therm. Anal. Calorim. 2010, 31, 416-429.

[39]. Criado, J. M.; Perez-Maqueda, L. A.; Sanchez-Jimenez, P. E. J. Therm. Anal. Calorim. 2005, 82, 671-675.
https://doi.org/10.1007/s10973-005-0948-3


How to cite


Nalini, G.; Jayachandramani, N.; Suresh, R.; Thirumurugan, P.; Thanikachalam, V.; Manikandan, G.; Sankari, D. Eur. J. Chem. 2019, 10(1), 72-81. doi:10.5155/eurjchem.10.1.72-81.1812
Nalini, G.; Jayachandramani, N.; Suresh, R.; Thirumurugan, P.; Thanikachalam, V.; Manikandan, G.; Sankari, D. Synthesis, characterization and thermal decomposition of ethyl-2’-amino-5’-cyano-6’-(1H-indole-3yl)-2-oxospiro[indoline-3,4’-pyran]-3’-carboxylate under non‐isothermal condition in nitrogen atmosphere. Eur. J. Chem. 2019, 10(1), 72-81. doi:10.5155/eurjchem.10.1.72-81.1812
Nalini, G., Jayachandramani, N., Suresh, R., Thirumurugan, P., Thanikachalam, V., Manikandan, G., & Sankari, D. (2019). Synthesis, characterization and thermal decomposition of ethyl-2’-amino-5’-cyano-6’-(1H-indole-3yl)-2-oxospiro[indoline-3,4’-pyran]-3’-carboxylate under non‐isothermal condition in nitrogen atmosphere. European Journal of Chemistry, 10(1), 72-81. doi:10.5155/eurjchem.10.1.72-81.1812
Nalini, Ganesan, Natesan Jayachandramani, Radhakrishnan Suresh, Prakasam Thirumurugan, Venugopal Thanikachalam, Govindasamy Manikandan, & Dharmalingam Sankari. "Synthesis, characterization and thermal decomposition of ethyl-2’-amino-5’-cyano-6’-(1H-indole-3yl)-2-oxospiro[indoline-3,4’-pyran]-3’-carboxylate under non‐isothermal condition in nitrogen atmosphere." European Journal of Chemistry [Online], 10.1 (2019): 72-81. Web. 20 Aug. 2019
Nalini, Ganesan, Jayachandramani, Natesan, Suresh, Radhakrishnan, Thirumurugan, Prakasam, Thanikachalam, Venugopal, Manikandan, Govindasamy, AND Sankari, Dharmalingam. "Synthesis, characterization and thermal decomposition of ethyl-2’-amino-5’-cyano-6’-(1H-indole-3yl)-2-oxospiro[indoline-3,4’-pyran]-3’-carboxylate under non‐isothermal condition in nitrogen atmosphere" European Journal of Chemistry [Online], Volume 10 Number 1 (31 March 2019)

DOI Link: https://doi.org/10.5155/eurjchem.10.1.72-81.1812

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