Skip to main content
SpringerLink
Log in

Hydrolytic cleavage of bis(p-nitrophenyl) phosphate by Schiff base MnIII complexes containing morpholine pendants in Gemini 16-6-16 micelles

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

Catalytic efficiency of two Schiff base manganese(III) complexes toward the hydrolysis of bis(p-nitrophenyl) phosphate (BNPP) was evaluated in a micellar media formed by bis(hexadecyl-dimethylammonium)hexane bromide (abbr. 16-6-16, 2Br−) at 25°C. Effects of various reaction conditions on the hydrolysis of BNPP were systematically investigated. The observations obtained indicate that the two Mn(III) catalysts can efficiently promote hydrolysis of BNPP with a six order of magnitude rate enhancement relative to the background rate constant (k 0). Different structures of the two complexes lend to their distinguishing activities each other. Furthermore, rates of BNPP hydrolysis in Gemini 16-6-16 micellar medium are much higher than that in hexadecyltrimethylammonium bromide (CTAB) and n-lauroylsarcosine sodium (LSS) micelles.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Mancin F and Tecilla P 2007 New J. Chem. 31 800

    Article  CAS  Google Scholar 

  2. Dixon N E, Geue R J, Lambert J N, Moghaddas S, Pearce D A and Sargeson A M 1996 Chem. Commun. 1287

  3. Wilcox D E 1996 Chem. Rev. 96 2435

    Article  CAS  Google Scholar 

  4. Karlin K D 1993 Science 261 701

    Article  CAS  Google Scholar 

  5. Kady I O and Tan B 1995 Tetrahedron Lett. 36 4031

    Article  CAS  Google Scholar 

  6. Chin J 1997 Curr. Opin. Chem. Biol. 1 514

    Article  CAS  Google Scholar 

  7. Rosch M A and Trogler W C 1990 Inorg. Chem. 29 2409

    Article  Google Scholar 

  8. Yang M Y, Iranzo O, Richard J P and Morrow J R 2005 J. Am. Chem. Soc. 127 1064

    Article  CAS  Google Scholar 

  9. Ichikawa K, Tarnai M, Uddin M K, Nakata K and Sato S 2002 J. Inorg. Biochem. 91 437

    Article  CAS  Google Scholar 

  10. Abuhijleh A L 1997 Polyhedron 16733

    Article  CAS  Google Scholar 

  11. Lykourinou-Tibbs V, Ercan A and Ming L-J 2003 Catal. Commun. 4 549

    Article  CAS  Google Scholar 

  12. Meier B W, Gomez J D, Kirichenko O V and Thompson J A 2007 Chem. Res. Toxicol. 20 199

    Article  CAS  Google Scholar 

  13. Rogers K R, Wang Y, Mulchandani A, Mulchandani P and Chen W 1999 Biotechnol. Prog. 15 517

    Article  CAS  Google Scholar 

  14. Kuo L Y and Perera N M 2000 Inorg. Chem. 39 2103

    Article  CAS  Google Scholar 

  15. Zeng W, Li J Z, Mao Z H, Hong Z and Qin S Y 2004 Adv. Synth. Catal. 346 1385

    Article  CAS  Google Scholar 

  16. Krishnan R and Vancheesan S 1999 J. Mol. Catal. A-Chem. 142 377

    Article  CAS  Google Scholar 

  17. Tsumaki T 1938 Bull. Chem. Soc. Jpn. 13 252

    Article  CAS  Google Scholar 

  18. Chen D and Martell A E 1987 Inorg. Chem. 26 1026

    Article  CAS  Google Scholar 

  19. Yan J, Li J Z, Li K B, Zhou B, Zeng W and Qin S Y 2006 Transit. Met. Chem. 31 286

    Article  CAS  Google Scholar 

  20. Zhang W, Loebach J L, Wilson S R and Jacobsen E N 1990 J. Am. Chem. Soc. 112 2801

    Article  CAS  Google Scholar 

  21. Jacobsen E N and Deng L 1994 Tetrahedron 50 4323

    Article  CAS  Google Scholar 

  22. Yamada T, Inagawa K, Nagata T and Mukaiyama T 1992 Chem. Lett. 2231

  23. Takai T, Hata E, Yorozu K and Mukaiyama T 1992 Chem. Lett. 2077

  24. Li J Z, Li H B, Zhou B, Zeng W, Qin S Y, Li S X and Xie J Q 2005 Transit. Met. Chem. 30 278

    Article  CAS  Google Scholar 

  25. Zhang Z S, Yu X M, Fong L K and Margerum L D 2001 Inorg. Chim. Acta 317 72

    Article  CAS  Google Scholar 

  26. Jiang B Y, Du J, Hu C W, Zeng X C and Cao Y S 2004 Transit. Met. Chem. 29 361

    Article  CAS  Google Scholar 

  27. Wang Y, Hu W, Li M J, Jiang W D and Hu C W 2006 Chem. Res. Appl. 18 1393 (in Chinese)

    CAS  Google Scholar 

  28. Moss R A and Jiang W G 2000 Langmuir 16 49

    Article  CAS  Google Scholar 

  29. Xiang Q X, Yu X Q, Su X Y, Yan Q S, Wang T, You J S and Xie R G 2002 J. Mol. Catal. A: Chem. 187 195

    Article  CAS  Google Scholar 

  30. Menger F M, Gan L H, Johnson E and Durst D H 1987 J. Am. Chem. Soc. 109 2800

    Article  CAS  Google Scholar 

  31. Jiang W D, Xu B, Li J Z, Xie J Q, Fu H Y, Chen H and Zeng X C 2006 J. Disper. Sci. Tech. 27 869

    Article  CAS  Google Scholar 

  32. Moss R A, Gong P K and Morales-Rojas H 2002 Org. Lett. (Lett.) 4 1835

    CAS  Google Scholar 

  33. Scrimin P, Tecilla P and Tonellato U 1991 J. Org. Chem. 56 161

    Article  CAS  Google Scholar 

  34. Menger F M and Keiper J S 2000 Angew. Chem. Int. Ed. 39 1906

    Article  Google Scholar 

  35. Zana R 1996 Langmuir 12 1208

    Article  CAS  Google Scholar 

  36. Song L D and Rosen M J 1996 Langmuir 12 1149

    Article  CAS  Google Scholar 

  37. De S, Aswal V K, Goyal P S and Bhattacharya S 1998 J. Phys. Chem. B102 6152

    Google Scholar 

  38. Lu T, Han F, Mao G R, Lin G F, Huang J B, Huang X, Wang Y L and Fu H L 2007 Langmuir 23 2932

    Article  CAS  Google Scholar 

  39. Zana R, Benrraou M and Rueff R 1991 Langmuir 7 1072

    Article  CAS  Google Scholar 

  40. Mahendra S B and Surekha D 2006 Adv. Colloid Interf. Sci. 123–126 387

    Google Scholar 

  41. Rosen M J and Tracy D J 1998 J. Surfactants Deterg. 1 547

    Article  CAS  Google Scholar 

  42. Zana R 1996 Curr. Opin. Colloid Interf. Sci. 1 566

    Article  CAS  Google Scholar 

  43. Jiang W D, Xu B, Lin Q, Li J Z, Liu F A, Zeng X C and Chen H 2008 Colloids Surfaces A: Physicochem. Eng. Aspects 315 103

    Article  CAS  Google Scholar 

  44. Jiang W D, Xu B, Lin Q, Li J Z, Fu H Y, Zeng X C and Chen H 2007 J. Colloid Interf. Sci. 311 530

    Article  CAS  Google Scholar 

  45. Qiu L G, Jiang X, Gu L N and Hu 2007 J. Mol. Catal. A: Chem. 277 15

    Article  CAS  Google Scholar 

  46. Qiu L G, Jiang X, Gu L N and Hu G 2007 J. Mol. Catal. A: Chem. 277 15

    Article  CAS  Google Scholar 

  47. Olivera-Nappa A, Andrews B A and Asenjo J A 2004 Biotechnol. Bioeng. 86 573

    Article  CAS  Google Scholar 

  48. Frieden C A and Alberty R A 1955 J. Biol. Chem. 212 859

    CAS  Google Scholar 

  49. Young M J, Wahnon D, Hynes R C and Chin J 1995 J.Am. Chem. Soc. 117 9441

    Article  CAS  Google Scholar 

  50. Chin J, Banaszczyk M, Jubian V and Zou X 1989 J. Am. Chem. Soc. 111 186

    Article  CAS  Google Scholar 

  51. Hendry P and Sargeson A M 1989 J. Am. Chem. Soc. 111 2521

    Article  CAS  Google Scholar 

  52. Suh J 1992 Acc. Chem. Res. 25 273

    Article  CAS  Google Scholar 

  53. Weijnen J G J, Koudijs A, Schellekens G A and Engbersen J F J 1992 J. Chem. Soc. Perkin Trans. II 829

  54. Gellman S H, Petter R and Breslow R 1986 J. Am. Chem. Soc. 108 2388

    Article  CAS  Google Scholar 

  55. Anatoly K Y 2005 Coord. Chem. Rev. 249 1997

    Article  CAS  Google Scholar 

  56. Morrison J F and Heyde E 1972 Annu. Reo. Biochem. 41 29

    Article  CAS  Google Scholar 

  57. Jiang B Y, Xiang Y, Du J, Xie J Q, Hu C W and Zeng X C 2004 Colloid Surf. A: Physicochem. Eng. Aspects 235 145

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Key Laboratory of Green Chemistry and Technology, Sichuan University of Science and Engineering, Zigong, 643 000, China

    Weidong Jiang, Bin Xu, Junbo Zhong, Jianzhang Li & Fuan Liu

Authors
  1. Weidong Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bin Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Junbo Zhong
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jianzhang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Fuan Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Weidong Jiang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jiang, W., Xu, B., Zhong, J. et al. Hydrolytic cleavage of bis(p-nitrophenyl) phosphate by Schiff base MnIII complexes containing morpholine pendants in Gemini 16-6-16 micelles. J Chem Sci 120, 411–417 (2008). https://doi.org/10.1007/s12039-008-0065-5

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-008-0065-5

Keywords

Search

Navigation