Microwave-assisted Synthesis, Crystal and Molecular Structure, and DFT Study of 1-(2-aminoethyl)-2-imidazolidinethione
DOI:
https://doi.org/10.29356/jmcs.v49i4.1320Keywords:
Imidazolidinethione, microwave, theoretical calculations, X ray crystallographyAbstract
Abstract. A fast microwave-assisted procedure for synthesizing 1-(2-
aminoethyl)-2-imidazolidinethione (1) is described. The crystal and molecular structure was determined. The combination of an X-ray
crystallographic study and theoretical calculations (DFT) provided
insight into the understanding of the high performance of this compound as low toxicity corrosion inhibitor.
Resumen. Se describe un método rápido de síntesis asistida por
microondas para la preparación de 1-(2-aminoetil)-2-imidazolidíntiona
(1). La combinación del estudio cristalográfico por difracción de rayos X y los cálculos teóricos (DFT) proporcionan información para entender el alto desempeño de este compuesto como inhibidor de la corrosión de baja toxicidad.
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References
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2. a) Ascher, Gerd; Heilmayer, Werner; Ludescher, Johannes. Synthesis and antibiotic activity of cephalosporines having cyclic aminoguanidine substituents. PCT Int. Appl. WO 9948896 A1
19990930 (1999). Chem. Abst. 131: 257380. b) Arnould, J. C.; Boutron, P.; Pasquet, M. J. Eur. J. Med. Chem. 1992, 27, 131-140.
3. Philippe, P. Low-toxicity corrosion inhibitor. PCT Int. Appl. WO 9851902 A1 19981119 (1998). Chem. Abst. 130: 16162.
4. a) Microwaves in Organic Synthesis (Ed: A. Loupy), Wiley- VCH, Weinheim, 2002. b) B. L. Hayes, Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, 2002. c) Microwave-Assisted Organic Synthesis (Ed: P Lidstöm, J. P. Tierney), Blackwell Scientific, 2005. d) Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry, Wiley-VCH, Weinheim, 2005.
5. a) Wang, D; Li, S.; Ying, Y.; Wang, M.; Xiao, H.; Chen, Z. Corrosion Sci. 1999, 4, 1911. b) Ramachandran, S.; Jovancicevic, V. Corrosion 1999, 55, 259. c) Jovancicevic, V., Ramachandran, S. ; Prince, P. Corrosion 1999, 55, 449. d) Cruz, J.; Martínez-Aguilera, L. M. R.; Salcedo, R.; Castro, M. Int. J. Quan. Chem. 2001, 85, 546; and ref. 1, 191-251.
6. a) Martínez-Palou, R.; Rivera, J.; Zepeda, L. G.; Hernández, M. A.; Marin, J.; Estrada, A. Corrosion 2004, 60, 465-470. b) García, E.; Cruz, J.; Martínez-Palou, R.; Genesca, J. J. Electranal. Chem. 2004, 566, 111-121. c) Martínez-Palou, R.; Zepeda, L. G.; Höpfl, H.; Montoya, A.; Guzmán-Lucero, D.; Guzmán, J. Mol. Diversity, in press.
7. a) Paz, G.; Marin, J.; Zepeda, L. G.; Martínez-Palou, R. Synlett 2003, 1847-1849. b) Fuentes, A.; Martínez-Palou, R.; Jiménez-Vázquez, H. A.; Delgado, F.; Reyes, A.; Tamariz, J. Monatsh Chem. 2005, 136, 177-192. c) Guzmán, D.; Guzmán, J.; Litkatchev, D.; Martínez-Palou, R. Tetrahedron Lett. 2005, 46, 1119-1122 and ref. 6c.
8. Web page: http://www.sevmexico.com
9. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery,J. A. Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.;
Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox,
D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; González, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 1998.
10. Becke, A. D. Phys. Rev. A 1998, 38, 3098.
11. a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. b) Miechlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
12. a) Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 864. b) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
13. a) Parr, R. G.; Yang, W. J. Am. Chem. Soc. 1984, 106, 4049. b) Yang, W.; Mortier, W.; J. Am. Chem. Soc. 1986, 108, 5708. c) Contreras, R.; Fuentealba, P.; Galván, M.; Pérez, P.; Chem. Phys. Lett. 1999, 304, 405. d) Fuentealba, P.; Pérez, P.; Contreras, R.; J. Chem. Phys. 2000, 113, 2544.
14. a) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989. b) Yang, W.; Parr, R. G. Proc. Natl. Acad. Sci. USA 1985, 82, 6723.
15. Bruker Analytical X-ray Systems. SMART: Bruker Molecular Analysis Research Tool, Version 5.618, 2000.
16. Bruker Analytical X-ray Systems. SAINT + NT, Version 6.04, 2001.
17. Sheldrick, G. M. SHELX86, Program for Crystal Structure Solution, University of Göttingen, Göttingen (Germany), 1986.
18. Bruker Analytical X ray Systems. SHELXTL-NT Version 6.10, 2000.
19. PLATON, version 210103, Spek, A. L. Acta Cryst. 1990, A46, C-34.
20. a) Feng, J.-C. ; Meng, Q.-H.; Liu, Y.; Dai, L. Org. Prep. Proc. Int. 1997, 29, 687. b) Aghapoor, K.; Heravi, M. M.; Nooshabadi, M. A. Indian J. Chem. 1998, 37B, 84. c) Khajavi, M. S.; Hajihadi, M.; Nikpour, F. J. Chem. Res. 1996, 2, 94.
21. Kerneur, G.; Lereftif, J. M.; Bazureau, J. P. ; Hamelin, J. Synthesis 1997, 287.
22. Valdés-Martínez, J.; Li, D. T.; Swearingen, J. K.; Kaminski, W.; Kelman, D. R.; West, D. X. Rev. Soc. Quím. Méx. 2004, 48, 235.
23. a) Chieh, C.; Cheung, S. K.; Can. J. Chem. 1983, 61, 211.b) Wheatley, P. J.; Acta Cryst. 1953, 6, 369. c) Mak, T. C. W.; Jasim, K. S.; Chieh, C. Can. J. Chem. 1984, 62, 808. d) Battaglia, L. P.; Corradi, A. B.; Nardelli, M. Croat. Chem. Acta 1984, 57, 545. e) Denk, M. K.; Gupta, S.; Brownie, J.; Tajammul, S.;
Lough A. J. Chem. Eur. J. 2001, 7, 4477. f) Schwindinger, W.; Fawcett, T. G.; Potenza, J. A.; Schugar, H. J.; Lalancette, R. A. Acta Cryst. 1980, B36, 1232.
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