Collect. Czech. Chem. Commun. 2006, 71, 1642-1658
https://doi.org/10.1135/cccc20061642

Cleavage of 4-Nitrophenyl Diphenyl Phosphate by Isomeric Quaternary Pyridinium Ketoximes - How Can Structure and Lipophilicity of Functional Surfactants Influence Their Reactivity in Micelles and Microemulsions?

Milan Kivala, Radek Cibulka and František Hampl*

Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic

References

1a. Fendler J. H., Fendler E. J.: Catalysis in Micellar and Macromolecular Systems, Chap. 5. Academic Press, New York 1975.
1b. Fendler J. H.: Membrane Mimetic Chemistry, Chap. 12. Wiley, New York 1982.
1c. Tonellato U. in: Solution Chemistry of Surfactants (K. L. Mittal, Ed.), Vol. 2, p. 541. Plenum Press, New York 1979.
1d. Feiters M. C. in: Comprehensive Supramolecular Chemistry (D. N. Reinhoudt, Ed.), Vol. 10, p. 311. Elsevier, Amsterdam 1996.
1e. Savelli G., Germani R., Brinchi L.: Surf. Sci. Ser. 2001, 100, 175.
1f. Oehme G. in: Aqueous-Phase Organometallic Catalysis (B. Cornils and W. A. Herrmann, Eds), p. 193. Wiley-VCH, Weinheim 2004.
2a. Benschop H. P., De Jong L. P. A.: Acc. Chem. Res. 1988, 21, 368. <https://doi.org/10.1021/ar00154a003>
2b. Yang Y.-C., Baker J. A., Ward J. R.: Chem. Rev. 1992, 92, 1729. <https://doi.org/10.1021/cr00016a003>
2c. Yang Y.-C.: Acc. Chem. Res. 1999, 32, 109. <https://doi.org/10.1021/ar970154s>
2d. Morales-Rojas H., Moss R. A.: Chem. Rev. 2002, 102, 2497. <https://doi.org/10.1021/cr9405462>
3a. Ogino K., Yoshida T., Nishi K., Fujita T., Tagaki W.: Chem. Lett. 1991, 341. <https://doi.org/10.1246/cl.1991.341>
3b. Ogino K., Yoshida T., Yamamoto H., Tagaki W.: Chem. Lett. 1992, 1197. <https://doi.org/10.1246/cl.1992.1197>
4a. Romsted L. S., Yao J. H.: Langmuir 1999, 15, 326. <https://doi.org/10.1021/la9808263>
4b. Soldi V., Keiper J., Romsted L. S., Cuccovia I. M., Chaimovich H.: Langmuir 2000, 16, 59. <https://doi.org/10.1021/la990336q>
4c. Yao J. H., Romsted L. S.: Langmuir 2000, 16, 8771. <https://doi.org/10.1021/la000533l>
4d. Menger F. M., Keiper J. S., Mbadugha B. N. A., Caran K. L., Romsted L. S.: Langmuir 2000, 16, 9095. <https://doi.org/10.1021/la0003692>
5a. Kotoučová H., Cibulka R., Hampl F., Liška F.: J. Mol. Catal. A 2001, 174, 59. <https://doi.org/10.1016/S1381-1169(01)00178-9>
5b. Cibulka R., Hampl F., Kotoučová H., Mazáč J., Liška F.: Collect. Czech. Chem. Commun. 2000, 65, 227. <https://doi.org/10.1135/cccc20000227>
6a. Scrimin P., Tecilla P., Tonellato U.: J. Org. Chem. 1991, 56, 161. <https://doi.org/10.1021/jo00001a033>
6b. Scrimin P., Ghirlanda G., Tecilla P., Moss R. A.: Langmuir 1996, 12, 6235. <https://doi.org/10.1021/la960311g>
6c. Bunton C. A., Scrimin P., Tecilla P.: J. Chem. Soc., Perkin Trans. 2 1996, 419. <https://doi.org/10.1039/p29960000419>
7. Holzer W., von Philipsborn W.: Magn. Reson. Chem. 1989, 27, 511. <https://doi.org/10.1002/mrc.1260270602>
8. Hawkes G. E., Herwig K., Roberts J. D.: J. Org. Chem. 1974, 39, 1017. <https://doi.org/10.1021/jo00922a001>
9. Pallas 1.2, Prolog P software. CompuDrug Chemistry, Ltd., Budapest 1994.
10a. Bhattacharya S., Snehalatha K.: Langmuir 1997, 13, 378. <https://doi.org/10.1021/la960526q>
10b. Burnside B. A., Knier B. L., Mackay R. A., Dupont Durst H., Longo F. R.: J. Phys. Chem. 1988, 92, 4505. <https://doi.org/10.1021/j100326a050>
10c. Ghosh K. K., Satnami M. L.: Colloids Surf., A 2006, 274, 125. <https://doi.org/10.1016/j.colsurfa.2005.08.041>
11. Scrimin P., Tecilla P., Tonellato U., Bunton C. A.: Colloids Surf., A 1998, 144, 71. <https://doi.org/10.1016/S0927-7757(98)00652-9>
12. Myers D.: Surfaces, Interfaces, and Colloids, Principles and Applications, pp. 333–343. VCH Publishers, Weinheim 1991.
13. Bunton C. A., Nome F. A., Quina F. H., Romsted L. S.: Acc. Chem. Res. 1991, 24, 357. <https://doi.org/10.1021/ar00012a001>
14. Mancin F., Tecilla P., Tonellato U.: Langmuir 2000, 16, 227. <https://doi.org/10.1021/la9909594>
15. Armarego W. L. F., Perrin D. D.: Purification of Laboratory Chemicals, 4th ed. Butterwoth– Heinemann, Oxford 1996.
16. Gulick W. M., Jr., Geshe D. H.: J. Am. Chem. Soc. 1966, 88, 2928. <https://doi.org/10.1021/ja00965a009>
17. Merten H., Gilman H.: J. Am. Chem. Soc. 1954, 76, 5798. <https://doi.org/10.1021/ja01651a063>
18. Origin 6.1. OriginLab Corporation, Northampton 2000.
19. Terrier F., MacCormack P., Kizilian E., Hallé J. C., Demerseman P., Guir F., Lion C.: J. Chem. Soc., Perkin Trans. 2 1991, 153. <https://doi.org/10.1039/p29910000153>