Abstract
Alkaline hydrolysis of ethyl 4-nitrophenyl ethylphosphonate in organized nanosized systems based on dimeric surfactants and co-micelles [with cetyl(trimethyl)ammonium bromide as co-surfactant]. Transfer of the reaction from water to the micellar pseudophase accelerates the alkaline hydrolysis by a factor of 10 to 170. The maximum acceleration has been observed for tetraalkylammonium surfactant 16–3–16. The main factors responsible for micellar effects of surfactants are both substrate concentration and change of the reactivity of hydroxide ion in going from bulk water to surfactant micelles.
Article PDF
Similar content being viewed by others
Explore related subjects
Discover the latest articles, news and stories from top researchers in related subjects.Avoid common mistakes on your manuscript.
References
Turovskaya, M.K., Mikhailov, VA., Burakov, N.I., Kapitanov, I.V, Zubareva, T.M., Lobachev, V.L., Panchenko, B.V., and Prokop’eva, T.M., Russ. J. Org. Chem., 2017, vol. 53, p. 351. https://doi.org/10.1134/S107042801703006X
Haswell, S.J. and Watts, P., Green Chem., 2003, vol. 5, p. 240. https://doi.org/10.1039/b210539j
Pavez, P., Oliva, G., and Millán, D., Chem Eng., 2016, vol. 4, p. 7023. https://doi.org/10.1021/acssuschemeng.6b01923
Samiey, B., Cheng, C.-H., and Wu, J., J. Chem., 2014, article ID 908476. https://doi.org/10.1155/2014/908476
Bedford, C.T., Organic Reaction Mechanisms, Knipe, A.C., Ed., Wiley, 2018, p. 87.
Patel, U., Parekh, P., Sastry, N.V., Aswal, V.K., and Bahadur, P., J. Mol. Liq., 2017, vol. 225, p. 888. https://doi.org/10.1016/j.molliq.2016.11.017
Kamboj, R., Singh, S., Bhadani, A., Kataria, H., and Kaur, G., Langmuir, 2012, vol. 28, p. 11969. https://doi.org/10.1021/la300920p
Alam, Md.S., Siddig, A.M., and Mandal, A.B., Russ. J. Phys. Chem. A, 2018, vol. 92, p. 185. https://doi.org/10.1134/s0036024418010028
Scholz, N., Behnke, T., and Resch-Genger, U., J. Fluoresc., 2018, vol. 28, p. 465. https://doi.org/10.1007/s10895-018-2209-4
Zhang, Q., Gao, Z., Xu, F., and Tai, S., J. Colloid Interface Sci., 2012, vol. 371, p. 73. https://doi.org/10.1016/j.jcis.2011.12.076
Sadovskii, Yu., Solomoichenko, T.N., Turovskaya, M.K., Kapitanov, I.V., Piskunova, Zh.P., Kostrikin, M.K., Prokop’eva, T.M., and Popov, A.F., Theor. Exp. Chem., 2012, vol. 48, p. 122. https://doi.org/10.1007/s11237-012-9249-7
Kapitanov, I.V., Prokop’eva, T.M., Sadovskii, Yu.S., Solomoichenko, T.N., Turovskaya, M.K., Piskunova, Zh.P., Razumova, N.G., and Popov, A.F., Ukr. Khim. Zh., 2014, vol. 80, p. 30.
Bhattacharya, S. and Kumar, P.V., J. Org. Chem., 2004, vol. 69, p. 559. https://doi.org/10.1021/jo034745+
Mirgorodskaya, A.B., Valeeva, F.G., Lukashenko, S.S., Kushnazarova, R.A., Prokop’eva, T.M., Zubareva, T.M., Mikhailov, V.A., and Zakharova, L.Ya., J. Mol. Liq., 2018, vol. 250, p. 229. https://doi.org/10.1016/j.molliq.2017.11.175
Bunton, C.A., Adv. Colloid Interface Sci., 2006, vols. 123’126, p. 333. https://doi.org/10.1016/j.cis.2006.05.008
Berezin, I.V, Martinek, K., and Yatsimirskii, A.K., Russ. Chem. Rev., 1973, vol. 42, p. 787. https://doi.org/10.1070/RC1973v042n10ABEH002744
Wettig, S.D., Novak, P., and Verrall, R.E., Langmuir, 2002, vol. 18, p. 5354. https://doi.org/10.1021/la011782s
Wettig, S.D. and Verrall, R.E., J. Colloid Interface Sci., 2001, vol. 235, p. 310. https://doi.org/10.1006/jcis.2000.7348
Sood, A.K. and Sharma, S., Phys. Chem. Liq., 2016, vol. 54, p. 574. https://doi.org/10.1080/00319104.2016.1139711
Banipal, T.S., Sood, A.K., and Singh, K., J. Surfactants Deterg., 2011, vol. 14, p. 235. https://doi.org/10.1007/s11743-010-1217-4
Sood, A.K., Singh, K., Kaur, J., and Banipal, T.S., J. Surfactants Deterg., 2012, vol. 15, p. 327. https://doi.org/10.1007/s11743-011-1314-z
Kapitanov, I.V., Belousova, I.A., Shumeiko, A.E., Kostrikin, M.L., Prokop’eva, T.M., and Popov, A.F., Russ. J. Org. Chem., 2014, vol. 50, p. 694. https://doi.org/10.1134/S1070428014050133
Prokop’eva, T.M., Kapitanov, I.V., Belousova, I.A., Shumeiko, A.E., Kostrikin, M.L., Turovskaya, M.K., Razumova, N.G., and Popov, A.F., Russ. J. Org. Chem., 2015, vol. 51, p. 1083. https://doi.org/10.1134/S1070428015080047
Prokop’eva, T.M., Belousova, I.A., Turovskaya, M.K., Razumova, N.G., Panchenko, B.V., and Mikhailov, V.A., Russ. J. Org. Chem., 2018, vol. 54, p. 1630. https://doi.org/10.1134/S1070428018110027
Simanenko, Yu.S., Popov, A.F., Prokop’eva, T.M., Karpichev, E.A., Savelova, V.A., Suprun, I.P., and Bunton, C.A., Russ. J. Org. Chem., 2002, vol. 38, p. 1286. https://doi.org/10.1023/A:1021699628721
Zubareva, T.M., Anikeev, A.V., Karpichev, E.A., Kapitanov, I.V., Prokop’eva, T.M., and Popov, A.F., Theor. Exp. Chem., 2011, vol. 47, p. 108. https://doi.org/10.1007/s11237-011-9190-1
Zubareva, T.M., Anikeev, A.V., Karpichev, E.A., Red’ko, A.N., Prokop’eva, T.M., and Popov, A.F., Theor. Exp. Chem., 2011, vol. 47, p. 377. https://doi.org/10.1007/s11237-012-9230-5
Pal, J., Datta, S., Aswal, V.K., and Bhattacharya, S., J. Phys. Chem. B, 2012, vol. 116, p. 13239. https://doi.org/10.1021/jp304700t
Zana, R., Benrraou, M., and Rueff, R., Langmuir, 1991, vol. 7, p. 1072. https://doi.org/10.1021/la00054a008
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Additional information
Russian Text © The Author(s), 2020, published in Zhurnal Organicheskoi Khimii, 2020, Vol. 56, No. 1, pp. 70–77.
For communication I, see [1].
Rights and permissions
About this article
Cite this article
Zubareva, T.M., Belousova, I.A., Prokop’eva, T.M. et al. Reactivity of Inorganic α-Nucleophiles in Acyl Group Transfer Processes in Water and Surfactant Micelles: II.1 Alkaline Hydrolysis of Ethyl 4-Nitrophenyl Ethylphosphonate in Systems Based on Dimeric Cationic Surfactants. Russ J Org Chem 56, 53–58 (2020). https://doi.org/10.1134/S1070428020010091
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428020010091