Micellization and catalytic properties of cationic surfactants with head groups functionalized with a hydroxyalkyl fragment

Journal of Chemical and Engineering Data

Volumn 57, Issue 11, 2012, Pages 3153-3163

  Mirgorodskaya, Alla B ^a   Yackevich, Ekaterina I ^a   Syakaev, Victor V ^a   Zakharova, Lucia Ya ^a   Latypov, Shamil K ^a   Konovalov, Alexander I ^a  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

BINS; BIOPHYSICS; CARBON DIOXIDE; CATALYST ACTIVITY; DYES; SURFACE ACTIVE AGENTS; SURFACE POTENTIAL;

ALKYL CHAIN LENGTHS; BINDING CAPACITIES; BINDING CONSTANT; CARBONIC ACIDS; CATALYTIC EFFECTS; CATALYTIC PROPERTIES; MICROENVIRONMENTS; PSEUDOPHASE MODEL;

CATIONIC SURFACTANTS;

EID: 84868679058     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je300753d     Document Type: Article

References (57)

1. Bunton, C. A.; Savelli, G. Organic reactivity in aqueous micelles and similar assemblies Adv. Phys. Org. Chem. 1986, 22, 213-309
2. Onel, L.; Buurma, N. J. Reactivity in organised assemblies Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 2010, 106, 344-375
3. Zhang, X.; Wang, Ch. Supramolecular amphiphiles Chem. Soc. Rev. 2011, 40, 94-101
4. Kim, K. T.; Meeuwissen, S. A.; Nolte, R. J. M.; van Hest, J. C. M. Smart nanocontainers and nanoreactors Nanoscale. 2010, 2, 844-858
5. Han, Y.; Wang, Y. Aggregation behavior of gemini surfactants and their interaction with macromolecules in aqueous solution Phys. Chem. Chem. Phys. 2011, 13, 1939-1956
6. Tadros, T. F. Applied surfactants: principles and application; Wiley-VCH: Berlin, 2005.
7. Myers, D. Surfactant science and technology; John Wiley and Sons: Chichester, U.K., 2006.
8. Vaisman, L.; Wagner, H. D.; Marom, G. The role of surfactants in dispersion of carbon nanotubes Adv. Colloid Interface Sci. 2006, 128-130, 37-46
9. Medeiros, S. F.; Santos, A. M.; Fessi, H.; Elaissari, A. Stimuli-responsive magnetic particles for biomedical applications Int. J. Pharm. 2011, 403, 139-161
10. Biswas, S.; Hussain, S. A.; Deb, S.; Nath, R. K.; Bhattacharjee, D. Formation of complex films with water-soluble CTAB molecules Spectrochim. Acta, Part A 2006, 65, 628-636
11. Wan, Y.; Dongyuan, Z. On the Controllable Soft-Templating Approach to Mesoporous Silicates Chem. Rev. 2007, 107, 2821-2860
12. Okhapkin, I. M.; Lozinsky, V. I.; Vasilevskaya, V. V.; Khokhlov, A. R. In Nanoreactor Engineering for Life Sciences and Medicine; Ostafin, A.; Landfester, K., Eds.; Artech House: Boston, 2009.
13. Kellaway, L.; Warr, G. G. The effect of head-group on selective counterion binding to cationic surfactants J. Colloid Interface Sci. 1997, 193, 312-314
14. Raghavan, S. R.; Kaler, E. W. Highly Viscoelastic Wormlike Micellar Solutions Formed by Cationic Surfactants with Long Unsaturated Tails Langmuir 2001, 17, 300-306
15. Belousova, I.; Karpichev, E.; Prokop'eva, T.; Luk'yanova, L.; Savelova, V.; Popov, A. The effect of the nature of the head group on the micellar effects of functional/cationic co-micelles in acyl transfer reactions Theor. Exp. Chem. 2007, 43, 35-43
16. Brinchi, L.; Profio, P. D.; Germani, R.; Savelli, G.; Spretib, N.; Bunton, C. A. Effects of micellar head group structure on the spontaneous hydrolysis of methyl naphthalene-2-sulfonate. The role of perchlorate ion J. Chem. Soc., Perkin Trans. 1998, 2, 361-364
17. Chatterjee, A.; Maiti, C. S.; Sanyal, S. K.; Moulik, S. P. Micellization and related behaviors of N-cetyl-N-ethenolyl-N,N-dimethyl and N-cetyl-N,N-diethanolyl-N-methyl ammonium bromide Langmuir 2002, 18, 2998-3004
18. Jurašin, D.; Habuš, I.; Filipović-Vinceković, N. Role of the alkyl chain number and head groups location on surfactants self-assembly in aqueous solutions Colloids Surf., A 2010, 368, 119-128
19. Para, G.; Hamerska-Dudra, A.; Wilk, K. A.; Warszyński, P. Surface activity of cationic surfactants; influence of molecular structure Colloids Surf., A 2010, 365, 215-221
20. Harkot, J.; Jańczuk, B. Surface and volume properties of dodecyldimethylammonium bromide and benzyldimethyldodecylammonium bromide. I. Surface properties of dodecyldimethylammonium bromide and benzyldimethyldodecylammonium bromide J. Colloid Interface Sci. 2009, 331, 494-499
21. Hayami, Y.; Wataya, A.; Takiue, T.; Ikeda, N.; Matsubara, H.; Aratono, M. Adsorption and micelle formation of alkylammonium chloride- alkyltrimethylammonium chloride mixtures J. Colloid Interface Sci. 2007, 310, 240-245
22. Borse, M. S.; Devi, S. Importance of head group polarity in controlling aggregation properties of cationic gemini surfactants Adv. Colloid Interface Sci. 2006, 123-126, 387-399
23. Mirgorodskaya, A. B.; Bogdanova, L. R.; Kudryavtseva, L. A.; Lukashenko, S. S.; Konovalov, A. I. Role of surface potential in the catalytic action of micelles of cationic surfactant with a hydroxyalkyl fragment in the head group Russ. J. Gen. Chem. 2008, 78, 163-170
24. Svenson, S. Controlling surfactant self-assembly Curr. Opin. Colloid Interface Sci. 2004, 9, 201-212
25. Bakshi, M. S.; Singh, J.; Singh, K.; Kaur, G. Mixed micelles of cationic 12-2-12 gemini with conventional surfactants: the head group and counterion effects Colloids Surf., A 2004, 237, 61-71
26. Rodríguez, J. R.; Czapkiewicz, J. Conductivity and dynamic scattering studies on homologous alkylbenzyldimethylammonium chlorides in aqueous solutions Colloids Surf., A 1995, 101, 107-111
27. Pashirova, T. N.; Zhil'tsova, E. P.; Kashapov, R. R.; Lukashenko, S. S.; Litvinov, A. I.; Kadirov, M. K.; Zakharova, L. Ya.; Konovalov, A. I. Supramolecular systems based on 1-alkyl-4-aza-1-azoniabicyclo[2.2.2]octane bromides Russ. Chem. Bull. 2010, 9, 1699-1706
28. Dias, R. S.; Magno, L. M.; Valente, A. J. M.; Das, D.; Das, P. K.; Maiti, S.; Miguel, M. G.; Lindman, B. Interaction between DNA and Cationic Surfactants: Effect of DNA Conformation and Surfactant Headgroup J. Phys. Chem. B 2008, 112, 14446-14452
29. Dasgupta, A.; Das, P. K.; Dias, R. S.; Miguel, M. G.; Lindman, B.; Jadhav, V. M.; Gnanamani, M.; Maiti, S. Effect of headgroup on DNA-cationic surfactant interactions J. Phys. Chem. B 2007, 111, 8502-8508
30. Mitra, R. N.; Dasgupta, A.; Das, D.; Roy, S.; Debnath, S.; Das, P. K. Geometric Constraints at the Surfactant Headgroup: Effect on Lipase Activity in Cationic Reverse Micelles Langmuir 2005, 21 (26) 12115-12123
31. Zakharova, L. Ya.; Mirgorodskaya, A. B.; Yackevich, E. I.; Yurina, A. V.; Syakaev, V. V.; Latypov, S. K.; Konovalov, A. I. The polyethyleneimine + cationic surfactant systems: the self-organization and reactivity study J. Chem. Eng. Data 2010, 55, 5848-5855
32. Omar, A.-A. M. A.; Abdel-Khalek, N. A. Surface and Thermodynamic Parameters of Some Cationic Surfactants J. Chem. Eng. Data 1998, 43, 117-120
33. Zakharova, L. Ya.; Mirgorodskaya, A. B.; Zhiltsova, E. P.; Kudryavtseva, L. A.; Konovalov, A. I. In Molecular Encapsulation: Organic Reactions in Constrained Systems; Brinker, U. H.; Mieusset, J.-L., Eds; John Wiley and Sons: Chichester, U.K., 2010.
34. Zakharova, L. Ya.; Mirgorodskaya, A. B.; Zhiĺtsova, E. P.; Kudryavtseva, L. A.; Konovalov, A. I. Catalysis of nucleophilic substitution reactions in supramolecular systems Russ. Chem. Bull. (Engl. Transl.) 2004, 53, 1385-1401
35. Zakharova, L. Ya.; Valeeva, F. G.; Kudryavtsev, D. B.; Ibragimova, A. R.; Kudryavtseva, L. A.; Timosheva, A. P.; Kataev, V. E. Catalytic effect of multicomponent supramolecular systems in phosphoryl-group transfer reactions Kinet. Catal. 2003, 44, 547-551
36. Zakharova, L. Ya.; Ibragimova, A. R.; Valeeva, F. G.; Zakharov, A. V.; Mustafina, A. R.; Kudryavtseva, L. A.; Harlampidi, H. E.; Konovalov, A. I. Nanosized reactors based on polyethyleneimines: from microheterogeneous systems to immobilized catalysts Langmuir 2007, 23, 3214-3224
37. Voronin, M. A.; Valeeva, F. G.; Zakharova, L. Ya.; Giniyatullin, R. Kh.; Semenov, V. E.; Reznik, V. S. Regulation of the Rate of Hydrolysis of Phosphorus Acid Esters in Organized Systems Based on Amphiphilic Pyrimidinophanes Kinet. Catal. 2010, 51, 644-652
38. Dwars, T.; Paetzold, E.; Oehme, G. Reactions in micellar systems Angew. Chem., Int. Ed. 2005, 44, 7174-7199
39. Khan, M. N. Micellar catalysis; CRC Press, Taylor and Francis Group: New York, 2006.
40. Mirgorodskaya, A. B.; Kudryavtseva, L. A. Aqueous Solutions of Geminal Alkylammonium Surfactants as a Medium for Reactions of Long-Chain Amine Russ. J. Gen. Chem. 2009, 79, 42-48
41. Bunton, C. A. The dependence of micellar rate effects upon reaction mechanism Adv. Colloid Interface Sci. 2006, 123-126, 333-343
42. Das, D.; Das, P. Improving the Lipase Activity Profile in Cationic Water-in-Oil Microemulsions of Hydroxylated Surfactants Langmuir 2003, 19, 9114-9119
43. Zakharova, L.; Valeeva, F.; Zakharov, A.; Ibragimova, A.; Kudryavtseva, L.; Harlampidi, H. Micellization and Catalytic Activity of the Cetyltrimethylammonium Bromide-Brij-97-Water Mixed Micellar System J. Colloid Interface Sci. 2003, 263, 597-605
44. Al'bert, A.; Sergent, E. Konstanty ionizacii kislot i osnovanii; Khimiya: Moskva, 1974.
45. Berezin, I. V.; Martinek, K.; Yatsimirski, A. K. Physicochemical Foundations of Micellar Catalysis Russ. Chem. Rev. 1973, 42, 787-802
46. Mukerjee, P. The partial specific volume and the density of micelles of association colloidal electrolytes J. Phys. Chem. 1962, 66, 1733-1735
47. Wu, D.; Chen, A.; Johnson, C. S. An Improved Diffusion Ordered Spectroscopy Experiment Incorporating Bipolar Gradient Pulses J. Magn. Reson. 1995, 115, 260-264
48. 19F Heteronuclear Overhauser Spectroscopy (HOESY) NMR Methods in Inorganic and Organometallic Chemistry: Something Old and Something New Chem. Rev. 2005, 105, 2977-2998
49. Brand, T.; Cabrita, E. J.; Berger, S. Intermolecular Interaction as Investigated by NOE and Diffusion Studies Prog. Nucl. Magn. Reson. Spectrosc. 2005, 46, 159-196
50. Kudryavtsev, D. B.; Panteleeva, A. R.; Yurina, A. V.; Voloshina, A. D.; Lukashenko, S. S.; Zobov, V. V.; Khodyrev, Yu. P.; Mirgorodskaya, A. B.; Zakharova, L. Ya. Anticorrosive Effects and Antimicrobial Properties of Alkyldimethyl(hydroxyalkyl)ammonium Bromides Petroleum Chem. 2011, 51, 293-298
51. Bunton, C. A.; Ionescu, L. G. Hydrolysis of Di- and Trisubstituted Phosphate Esters Catalyzed by Nucleophilic Surfactants J. Am. Chem. Soc. 1973, 95, 2912-2917
52. Tishkova, E. P.; Fedorov, S. B.; Kudryavtseva, L. A.; Bel'skii, V. E.; Ivanov, B. E. Nucleophilic substitution in bis(4-nitrophenyl) ethyl phosphate in alkaline micellar solutions of 2-hydroxyethyldimethyloctadecylammonium bromide Russ. Chem. Bull. 1990, 60, 2302-2305
53. Mchedlov-Petrosyan, N. O. Differencirovanie sily organicheskikh kislot v istinnykh i organizovannykh rastvorakh; Izd. Khar'kovskogo nacional'nogo universiteta imeni V. N. Karazina: Khar'kov, 2004.
54. Soderman, O.; Stilbs, P. NMR studies of complex surfactant systems Prog. Nucl. Magn. Reson. Spectrosc. 1994, 26, 445-482
55. Jansson, M.; Stilbs, P. A comparative study of organic counterion binding to micelles with the Fourier transform NMR self-diffusion technique Text J. Phys. Chem. 1985, 89, 4868-4873
56. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy: High-Resolution Methods and Applications in Organic Chemistry and Biochemistry, 3 rd ed.; Gordon & Breach Science Pub: New York, 1987.
57. Menger, F. M.; Portnoy, C. T. The effect of urea and other reagents on the reactivity of associated p-nitrophenyl laurate J. Am. Chem. Soc. 1968, 90, 1875-1878