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Vol. 25 No. 5 (2013): Vol 25 Issue 5

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Synthesis and Theoretical Studies of 1,3,3,5,5-Pentachloro-1-mono-(2-amidopyridin)cyclotriphosphazene

https://doi.org/10.14233/ajchem.2013.13318
Safaa A. Ahmed
Department of Chemistry, College of Education Samarra, University of Tikrit, Tikrit-43001, Iraq

Corresponding Author(s) : Safaa A. Ahmed

drsafaa1954@gmail.com

Asian Journal of Chemistry, Vol. 25 No. 5 (2013): Vol 25 Issue 5

Abstract

1,3,3,5,5-Pentachloro-1-mono(2-amidopyridine)cyclotriphosphazene was prepared from hexachlorocyclotriphosphazene and 2-amino pyridine in acetone. The structure of the white crystals of the prepared compound was elucidated by the X-ray diffraction and supported by the FTIR and 1H, 13C, 31P NMR spectroscopy. Since the X-ray diffraction is not accurate in detecting the position of the hydrogen atoms, Density functional theory (B3LYP) was used to study the structure and the spectroscopic properties of the compound and its tautomers that belong to the hydrogen tautomerism. Calculations have shown that the isomer in which the hydrogen attached to the nitrogen atom of the amido nitrogen that attached to the pyridine ring has the lowest energy and that comes in accordance with 1H NMR and FTIR spectroscopy. Potential energy curve with calculated activation energy is reported.

Keywords

Triphosphazene Cyclotriphosphazine DFT Tautomerism Potential energy curve
A. Ahmed, S. (2012). Synthesis and Theoretical Studies of 1,3,3,5,5-Pentachloro-1-mono-(2-amidopyridin)cyclotriphosphazene. Asian Journal of Chemistry, 25(5), 2377–2382. https://doi.org/10.14233/ajchem.2013.13318
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References
  1. Albright and Wilson Ltd., GB Patent 1016642 (1966).
  2. Albright and Wilson Ltd., GB Patent 1017375 (1966).
  3. V. Chandrasekhar and K.R.J. Thomas, Struct. Bonding, 81, 41 (1993).
  4. B. Zanin, J.P. Faucher and J.F. Labarre, Inorg. Chim. Acta, 172, 147 (1990).
  5. J.P. Bonnet and J.F. Labarre, Inorg. Chim. Acta, 149, 187 (1988).
  6. H. Ibisoglu, Heterocycles, 71, 2173 (2007).
  7. G. Yenilmez Ciftçi, E. Tanriverdi and Y. Zorlu, Heterocycles, 75, 635 (2008).
  8. R. Andrews, IRCS Med. Sci., 7, 285 (1979).
  9. G. Guerch, J.F. Labarre, R. Lahana, R. Roques and F. Sournies, J. Mol. Struct., 99, 275 (1983).
  10. J. Liebig, Ann. Chem., 11, 139 (1834).
  11. J.H. Gladstone and J.D. Holmes, J. Chem. Soc., 17, 225 (1864).
  12. C.W. Allen, Chem. Rev., 91, 119 (1991).
  13. R.N. Das, R.A. Shaw, B.C. Smith and M. Woods, J. Chem. Soc., Dalton Trans., 709 (1973).
  14. D.J. Lingley, R.A. Shaw, M. Woods and S.S. Krishnamurthy, Phosphorus Sulfur, 4, 379 (1978).
  15. S. Das, R. Keat, R.A. Shaw and B.C. Smith, J. Chem. Soc., 5032 (1965).
  16. N.V. Mani and A.J. Wagner, Acta Crystallogr. B, 27, 51 (1971).
  17. M.J. Begley, D.B. Sowerby and T.T. Bamgboye, J. Chem. Soc., Dalton Trans., 1401 (1979).
  18. W. Polder and A.J. Wagner, Cryst. Struct. Commun., 5, 253 (1976).
  19. S. Ganapathiappan and S.S. Krishnamurthy, J. Chem. Soc., Dalton Trans., 585 (1987).
  20. V.B. Desai, R.A. Shaw and B.C. Smith, J. Chem. Soc. A, 2023 (1970).
  21. H. Lederle, G. Ottman and E. Kober, Znorg. Chem., 5, 1818 (1966).
  22. D.D. Perrin and W.L.F. Armagedo, Purification of Laboratory Chemicals, Perjamon Press, Oxford, edn. 3 (1988).
  23. S.A. Ahmed, R.A. Haque, Z.H. Zetty, H.-K. Fun and W.-S. Loh, Acta Cryst., E68, o306 (2012).
  24. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez and J.A. Pople, Gaussian 03, Revision C.02, Gaussian Inc., Wallingford CT (2004).
  25. H. Koopman, F.J. Spruit, F. Van Deursen and J.Bakker, Rec. Trav. Chem., 84, 341 (1965).
  26. U. Kropacheva and V.A. Parshina, Zhur. Obshchei. Khim., 35, 1988 (1965).
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