Notes

Burning-Rate Catalytic Properties of Ferrocenyl β-Diketones and Their Cu(II), Ni(II) Complexes

  • Zhu Xueyou ,
  • Li Xiaohong ,
  • Han Fengjiao ,
  • Zhang Shichen ,
  • Zhao Haiying ,
  • Bian Zhanxi
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  • Inner Mongolia Key Laboratory of Fine Organic Synthesis and College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021

Revised date: 2014-11-07

  Online published: 2014-12-02

Supported by

Project supported by the National Natural Science Foundation of China (No. 21102068), the Research Program of Science and Technology at Universities of Inner Mongolia (No. NJZZ001) and the Natural Science Foundation of Inner Mongolia (Nos. 2013MS0207, 2014JQ02).

Abstract

Ferrocenyl β-diketones containing benzene ring have been synthesized and characterized. The content of enol isomer is almost 100% in β-diketone containing nitro group, and decreases to 84% in that containing methoxy group in CDCl3 from 1H NMR. When they were converted to the Cu(II) or Ni(II) complexes, the stretching bands of C=O and C=C in enol isomers shifted 57~69 and 10~27 cm-1 to low wave number, respectively. The absorption bands below 300 nm assignabling to Fe(d)-π* and π-π* electronic transitions of the aromatic rings in UV-vis absorption spectra shifted bathochromically 5~17 nm. The thermogravimetry-differential scanning calorimetry (TG-DSC) measurements confirmed that not only the sublimation for ammonium perchlorate (AP) on the high-temperature decomposition stage was inhabited but also the obvious catalytic effect on the decomposition of AP was found after adding these ferrocenyl β-diketones or their Cu or Ni complexes to AP, and the Cu complexes had the most significant effect. The Cu complex containing methoxy group decreased the decomposition temperature of AP by 87 ℃. So the Cu complexes are more effective catalysts than ferrocenyl β-diketone ligands and the Ni complexes.

Cite this article

Zhu Xueyou , Li Xiaohong , Han Fengjiao , Zhang Shichen , Zhao Haiying , Bian Zhanxi . Burning-Rate Catalytic Properties of Ferrocenyl β-Diketones and Their Cu(II), Ni(II) Complexes[J]. Chinese Journal of Organic Chemistry, 2015 , 35(4) : 922 -926 . DOI: 10.6023/cjoc201410006

References

[1] Li, P. Z.; Liu, Z. Q. Eur. J. Med. Chem. 2011, 46, 1821.
[2] Purecha, V. H.; Nandurkar, N. S.; Bhanage, B. M.; Nagarkar, J. M. Tetrahedron Lett. 2008, 49, 5252.
[3] Zhao, H. Y.; Zhu, Y. Z.; Chen, C.; He, L.; Zheng, J. Y. Carbon 2012, 50, 4894.
[4] Gao, J. M.; Wang, L.; Yu, H. L.; Xiao, A. G.; Ding, W. B. Propellants, Explos., Pyrotech. 2011, 36, 404.
[5] Zhao, H. Y.; Guo, L.; Chen, S. F.; Bian, Z. X. RSC Adv. 2013, 3, 19929.
[6] Yu, H. J.; Wang, L.; Huo, J.; Ding, J. H.; Tan, Q. H. J. Appl. Polym. Sci. 2008, 110, 1594.
[7] Gore, G. M.; Tipare, K. R.; Bhatewara, R. G.; Prasad, U. S.; Gupta, M.; Mane, S. R. Def. Sci. J. 1999, 49, 151.
[8] Ye, H.; Wang, W.; Zhu, X.; Chen, W.; Xie, L.; Yuan, Y. Chin. J. Org. Chem. 2013, 33, 827 (in Chinese).
(叶宏民, 王薇, 朱晓晓, 陈伟强, 谢莉莉, 袁耀锋, 有机化学, 2013, 33, 827.)
[9] Cho, B. S.; Noh, S. T. J. Appl. Polym. Sci. 2011, 121, 3560.
[10] Xiao, F. J.; Feng, F. F.; Li, L. L.; Zhang, D. Propellants, Explos., Pyrotech. 2013, 38, 358.
[11] Guo, J. Y.; Zhang, J. Q.; Su, L. H.; Pang, W. Q.; Kou, K. C. J. North-Western Polytech. Univ. 2006, 24, 350 (in Chinese).
(国际英, 张教强, 苏力宏, 庞维强, 寇开昌, 西北工业大学学报, 2006, 24, 350.)
[12] Li, B. G.; Bian, Z. X.; Cao, L. Z. Chin. J. Appl. Chem. 2001, 18, 877 (in Chinese).
(李保国, 边占喜, 曹立志, 应用化学, 2001, 18, 877.)
[13] Grevels, F. W.; Kuran, A.; Ozkar, S.; Zora, M. J. Organomet. Chem. 1999, 587, 122.
[14] Singh, N. B.; Ojha, A. K. Thermochim. Acta 2002, 390, 67.
[15] Zhao, H.; Chen, M.; Zhu, X.; Chen, S.; Bian, Z. Res Chem. Intermed. 2013, DOI: 10.1007/s11164-013-1503-7
[16] Zhao, H. Y.; Guo, L.; Chen, S. F.; Bian, Z. X. J. Mol. Struct. 2013, 1054, 164.
[17] Gao, Y.; Li, H.; Ke, C.; Xie, L.; Wei, B.; Yuan, Y. Appl. Organomet. Chem. 2011, 25, 407.
[18] Vyazovkin, S.; Wight, C. A. Chem. Mater. 1999, 11, 3386.
[19] Liu, J.; Liu, Z.; Cheng, J.; Fang, D. J. Solid State Chem. 2013, 200, 43.
[20] Plessis, W. C.; Vosloo, T. G.; Swarts, J. C. J. Chem. Soc., Dalton Trans. 1998, 2507.
[21] Joubert, C. C.; van As, L.; Jakob, A.; Speck, J. M.; Lang, H.; Swarts, J. C. Polyhedron 2013, 55, 80.

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