The reaction of N,N-spiro bridged octachlorobis(cyclotriphosphazene) with 1,3-propanediol: Comparison with 1,2-ethanediol (original) (raw)

Abstract

The reaction of the N,N-spiro bridged octachlorobis(cyclotriphosphazene), {N 3 P 3 Cl 4 [br-N (CH 2) 5 CH 3 ] 2 N 3 P 3 Cl 4 } (1), in three stoichiometries (1:0.7, 1:2 and 1:4) with the disodium salt of 1,3propanediol in THF at room temperature produced seven products, whose structures have been characterized by elemental analysis, mass spectrometry, 1 H and 31 P NMR spectroscopy; also the crystal structures of 6 and 8 were determined by X-ray crystallography. The reactions gave a mixture of rearranged derivatives (2, 4 and 5) in which the central four membered cyclophosphazane ring transformed into a six-membered monocyclophosphazene ring, as well as the normal substituted derivatives (3, 6-8). In addition, the results of all the reactions were compared with previous work on the reactions of the starting compound 1 with the disodium derivative of 1,2-ethanediol, in the same mole ratios and in the same solvent, THF.

Loading...

Loading Preview

Sorry, preview is currently unavailable. You can download the paper by clicking the button above.

References (38)

  1. H.R. Allcock, Chemistry and Application of Polyphosphazenes, Wiley- Interscience, Hoboken, NJ, 2003.
  2. M. Gleria, R. De Jaeger (Eds.), Applicative Aspects of Cyclophosphazenes, Nova Science Publishers, New York, 2004.
  3. K. Inoue, T. Yamauchi, T. Itoh, E. Ihara, J. Inorg. Organomet. Polym Mater. 17 (2007) 367.
  4. V. Chandrasekhar, P. Thilagar, B.M. Pandian, Coord. Chem. Rev. 251 (2007) 1045.
  5. X. Li, F. Jiang, L. Chen, M. Wu, Q. Chen, Y. Bu, M. Hong, Dalton Trans. 41 (2012) 14038.
  6. D. Davarcı, S. Bes ßli, E. Demirbas ß, Liq. Cryst. 40 (2013) 624.
  7. Q. He, H. Dai, X. Tan, X. Cheng, F. Liu, C. Tschierskec, J. Mater. Chem. 1 (2013) 7148.
  8. J. Sun, Z. Yu, X. Wang, D. Wu, ACS Sustainable Chem. Eng. 2 (2014) 231.
  9. K. Krishnamoorthy, V. Selvaraj, Appl. Surf. Sci. 366 (2016) 148.
  10. D. Prasanna, V. Selvaraj, J. Colloid Interface Sci. 472 (2016) 116.
  11. C.W. Allen, D.E. Brown, S.D. Worley, Inorg. Chem. 39 (2000) 810.
  12. M. Bahadur, C.W. Allen, W.E. Geiger, A. Bridges, Can. J. Chem. 80 (2002) 1393.
  13. G.A. Carriedo, P. Crochet, F.J. Garcia-Alonso, J. Gimeno, A. Persa-Soto, Eur. J. Inorg. Chem. 18 (2004) 3668.
  14. B.A. Omotowa, B.S. Phillips, J.S. Zabinski, J.M. Shreeve, Inorg. Chem. 43 (2004) 5466.
  15. K. Muralidharan, B.A. Omotowa, B. Twamley, C. Piekarski, J.M. Shreeve, Chem. Commun. (2005) 5193.
  16. P.I. Richards, A. Steiner, Inorg. Chem. 44 (2005) 275.
  17. V. Chandrasekhar, G.T.S. Andavan, R. Azhakar, B.M. Pandian, Inorg. Chem. 47 (2008) 1922.
  18. E.W. Ainscough, A.M. Brodie, R.J. Davidson, B. Moubaraki, K.S. Murray, C.A. Otter, M.R. Waterland, Inorg. Chem. 47 (2008) 9182.
  19. K.R. Carter, M. Calichman, C.W. Allen, Inorg. Chem. 48 (2009) 7476.
  20. K. Keshav, N. Singh, A.J. Elias, Inorg. Chem. 49 (2010) 5753.
  21. R. Boomishankar, P.I. Richards, A.K. Gupta, A. Steiner, Organometallics 29 (2010) 2515.
  22. D. Kumar, N. Singh, K. Keshav, A.J. Elias, Inorg. Chem. 50 (2011) 250.
  23. S. Bes ßli, S.J. Coles, D.B. Davies, A.O. Erkovan, M.B. Hursthouse, A. Kılıç, Inorg. Chem. 47 (2008) 5042.
  24. S. Bes ßli, S.J. Coles, D.B. Davies, A. Kılıc, R.A. Shaw, Dalton Trans. 40 (2011) 5307.
  25. S. Bes ßli, F. Yuksel, D.B. Davies, A. Kılıc, Inorg. Chem. 51 (2012) 6434.
  26. S. Bes ßli, C. Mutlu Balcı, H. Cantürk, S. Dog ˘an, F. Yuksel, C.W. Allen, Inorg. Chem. 55 (2016) 7832.
  27. S. Bes ßli, S. Dog ˘an, C. Mutlu, F. Yüksel, Polyhedron 98 (2015) 230.
  28. Bruker, SADABS, Bruker AXS Inc., Madison, Wisconsin, USA, 2005.
  29. Bruker APEX2 (Version 2011.4-1). Bruker AXS Inc., Madison, Wisconsin, USA, 2008.
  30. G.M. Sheldrick, Acta Crystallogr. A 64 (2008) 112.
  31. A.L. Spek, Acta Crystallogr. D. 65 (2009) 148.
  32. C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P.A. Wood, J. Appl. Crystallogr. 41 (2008) 466.
  33. K. Brandenburg, DIAMOND 3.1 for Windows. Crystal Impact GbR, Bonn, Germany, 2006.
  34. S.R. Contractor, M.B. Hursthouse, L.S. Shaw, R.A. Shaw, H. Yılmaz, Acta Crystallogr. Sect. B. (1985) 122.
  35. E. Tanrıverdi Ecik, S. Bes ßli, G. Yenilmez Ciftci, D.B. Davies, A. Kılıc, F. Yuksel, Dalton Trans. 41 (2012) 6715.
  36. V. Chandrasekhar, S.S. Krishnamurthy, H. Manohar, A.R.V. Murthy, R.A. Shaw, M. Woods, J. Chem. Soc., Dalton Trans. (1984) 621.
  37. D. Cremer, J.A. Pople, J. Am. Chem. Soc. 97 (1975) 1354.
  38. S. Bes ßli, S.J. Coles, D.B. Davies, M.B. Hursthouse, A. Kılıç, R.A. Shaw, Dalton Trans. (2007) 2792.