Abstract
In recent years our reseach group has investigated the chemical behaviour of β-cyclodextrin (CD)/surfactant mixed systems and their characteristics as reaction media. The results have been interpreted in terms of a pseudophase model that takes into account the formation of both CD-surfactant and CD-substrate complexes and also, in some cases, the exchange of X- and OH- ions between the micellar and aqueous pseudophases. from the experimental results it was concluded that the presence of CD has no effect on existing micelles but raises the critical micellar concentration (cmc). on the other hand, at surfactant concentrations above the cmc, competition between the micellisation and complexation processes leads to the existence of a significant concentration of free CD in equilibrium with the micellar aggregates. The percentage of uncomplexed β-CD in equilibrium with the micellar system increases on increasing the hydrophobicity of the surfactant molecule. This behaviour was justified taking into account the existence of two simultaneous processes: complexation of surfactant monomers by CD and the process of self-assembly to form micellar aggregates. The autoaggregation of surfactant monomers is more important than the complexation process in this mixed system. Varying the hydrophobicity of the surfactant monomer enabled us to determine that the percentages of uncomplexed CD in equilibrium with the micellar system were in the range of 5-95%. When the surfactant self-assembly structure is a vesicle, the free CD in the CD/surfactant mixed system yields a percentage of 100%.
References
1.
Bender M.
, and
Komiyama M.
(1978 ) Cyclodextrin chemistry. SpringerVerlag , New York .
2.
Saenger W.
(1980 ) Angew. Chem., Int. Ed. Engl. , 19 , 344 .
3.
Fendler J.H.
, and
Fendler E.J.
(1975 ) Catalysis in micellar and macromolecular systems. Academic Press , New York .
4.
Coleman A.W.
,
Nicolis I.
,
Keller N.
, and
Dalbiez J.P.
(1992 ) J. Incl. Phenom. Mol. Recognit. Chem. , 13 , 139 .
5.
Sanemasa I.
, and
Akamine Y.
(1987 ) Bull. Chem. Soc. Jpn. , 60 , 2059 .
6.
Fujiki M.
,
Deguchi T.
, and
Sanemasa I.
(1988 ) Bull. Chem. Soc. Jpn. , 61 , 1163 .
7.
Sanemasa I.
,
Takuma T.
, and
Deguchi T.
(1989 ) Bull. Chem. Soc. Jpn. , 62 , 3098 .
8.
Tee O.S.
(1994 ) Adv. Phys. Org. Chem. , 29 , 1 –85 .
9.
Wenz G.
(1994 ) Angew. Chem., Int. Ed. Engl. , 33 , 803 –822 .
10.
Kalyanasundaram K.
(1987 ) Photochemistry in microheterogeneous systems. Academic Press , New York .
11.
Ramamurthy V.
, and
Eaton D.F.
(1988 ) Acc. Chem. Res. , 21 , 300 –306 .
12.
Ramamurthy V.
,
Weiss R.G.
, and
Hammond G.S.
(1993 ) Adv. Photochem. , 18 , 67 –236 .
13.
Connors K.A.
(1997 ) Chem. Rev. , 97 , 1325 –1357 .
14.
Rekharsky M.V.
,
Mayhew M.P.
,
Goldberg R.N.
,
Ross P.D.
,
Yamashoji Y.
, and
Inoue Y.
(1997 ) J. Phys. Chem. B , 101 , 87 –100 .
15.
Szejtli J.
, and
Osa T.
(eds.), (1996 ) Comprehensive supramolecular chemistry , Vol. 3 , Cyclodextrins, Pergamon , New York .
16.
Muñoz de la Peña A.
,
Ndou T.T.
,
Zung J.B.
,
Greene K.L.
,
Live D.H.
, and
Warner I.M.
(1991 ) J. Am. Chem. Soc. , 113 , 1572 –1577 .
17.
Li S.
, and
Purdy W.C.
(1992 ) Chem. Rev. , 92 , 1457 –1470 .
18.
Sbai M.
,
Ait Lyazidi A.
,
Lerner D.A.
,
del Castillo B.
, and
Martin M.A.
(1995 ) Anal. Chim. Acta , 303 , 47 –55 .
19.
Astray G.
,
Gonzalez-Barreiro C.
,
Mejuto J.C.
,
Rial-Otero R.
, and
Simal-Gándara J.
(2009 ) Food Hydrocolloids , 23 , 1631 –1640 .
20.
Hamasaki K.
,
Ikeda H.
,
Nakamura A.
,
Ueno A.
,
Toda F.
,
Suzuki I.
, and
Osa T.
(1993 ) J. Am. Chem. Soc. , 115 , 5035 –5040 .
21.
Evans C.H.
,
De Feyter S.
,
Viaene L.
,
van Stam J.
, and
De Schryver F.C.
(1996 ) J. Phys. Chem. , 100 , 2129 –2135 .
22.
Bunton C.A.
, and
Savelli G.
(1986 ) Adv. Phys. Org. Chem. , 22 , 213 –309 .
23.
Cordes E.H.
(1978 ) Pure Appl. Chem. , 50 , 617 –625 .
24.
García-Río L.
,
Mejuto J.C.
,
Pérez-Lorenzo M.
, and
Rodríguez-Dafonte P.
(2006 ) Prog. React. Kinet. Mech. , 31 , 129 –138 .
25.
Jobe D.J.
,
Reinsborough V.C.
, and
Wetmore S.C.
(1995 ) Langmuir , 11 , 2476 .
26.
Utsuki T.
,
Brem H.
,
Pitha J.
,
Loftsson T.
,
Kristmundsdottir T.
,
Tyler B.M.
, and
Olivi A.
(1996 ) J. Control. Rel. , 40 , 251 .
27.
Nicolle G.M.
, and
Merbach A.E.
(2004 ) Chem. Commun. , 854 .
28.
Valente A.J.M.
,
Nilsson M.
, and
Soderman O.
(2005 ) J. Colloid Interface Sci. , 281 , 218 .
29.
Palepu R.
,
Richardson J.E.
, and
Reinsborough V.C.
(1989 ) Langmuir , 5 , 218 .
30.
Rafati A.A.
,
Bagheri A.
,
Iloukhani H.
, and
Zarinehzad M.
(2004 ) J. Mol. Liq. , 116 , 37 .
31.
Junquera E.
,
Gonzalez Benito J.
,
Pena L.
, and
Aicart E.
(1994 ) J. Colloid Interface Sci. , 163 , 355 .
32.
Gonzalez-Gaitano G.
,
Crespo A.
,
Compostizo A.
, and
Tardajos G.
(1997 ) J. Phys. Chem. B , 101 , 4413 .
33.
Cabaleiro-Lago C.
,
Nilsson M.
, and
Söderman O.
(2005 ) Langmuir , 21 , 11637 .
34.
Patonay G.
,
Rollie M.E.
, and
Warner I.M.
(1985 ) Anal. Chem. , 57 , 569 .
35.
Jiang Y.-B.
, and
Wang X.-J.
(1994 ) Appl. Spectrosc. , 48 , 1428 .
36.
Rafati A.A.
, and
Bagheri A.
(2004 ) Bull. Chem. Soc. Jpn. , 77 , 485 .
37.
Jezequel D.
,
Mayaffre A.
, and
Letellier P.
(1991 ) Can. J. Chem. , 69 , 1865 .
38.
Bakshi M.S.
(2000 ) J. Colloid Interface Sci. , 227 , 78 .
39.
García-Río L.
,
Hervés P.
,
Iglesias E.
,
Leis J.R.
,
Mejuto J.C.
, and
Pérez-Juste J.
(2000 ) Recent Res. Dev. Phys. Chem. , 4 , 101 .
40.
Guo R.
,
Zhu X.J.
, and
Guo X.
(2003 ) Colloid Polym. Sci. , 281 , 876 .
41.
Dharmawardana U.R.
,
Christian S.D.
,
Tucker E.E.
,
Taylor R.W.
, and
Scamehorn J.F.
(1993 ) Langmuir , 9 , 2258 –2263 .
42.
Hersey A.
,
Robinson B.H.
, and
Kelly H.C.
(1986 ) J. Chem. Soc., Faraday Trans. , 82 , 1271 –1287 .
43.
De Lisi R.
,
Lazzara G.
,
Milioto S.
,
Muratore N.
, and
Terekhova I.V.
(2003 ) Langmuir , 19 , 7188 .
44.
De Lisi R.
,
Lazzara G.
,
Milioto S.
, and
Muratore N.
(2003 ) J. Phys. Chem. B , 107 , 13150 .
45.
De Lisi R.
,
Milioto S.
, and
Muratore N.
(2002 ) J. Phys. Chem. B , 106 , 8944 .
46.
Castro A.
,
Leis J.R.
, and
Peña M.E.
(1990 ) J. Chem. Soc., Perkin Trans. , 2, 1221 –1225 .
47.
Bravo C.
,
Hervés P.
,
Leis J.R.
, and
Peña M.E.
(1990 ) J. Phys. Chem. , 94 , 8816 –8820 .
48.
Bravo C.
,
Leis J.R.
, and
Peña M.E.
(1992 ) J. Phys. Chem. , 96 , 1957 –1961 .
49.
García-Río L.
,
Iglesias E.
,
Leis J.R.
, and
Peña M.E.
(1992 ) J. Phys. Chem. , 96 , 7820 –7823 .
50.
García-Río L.
,
Mejuto J.C.
,
Nieto M.
,
Pérez-Juste J.
,
Pérez-Lorenzo M.
, and
Rodríguez-Dafonte P.
(2005 ) Supramol. Chem. , 17 , 649 –653
51.
García-Río L.
,
Hervés P.
,
Leis J.R.
,
Mejuto J.C.
,
Pérez-Juste J.
, and
Rodríguez-Dafonte P.
(2006 ) Org. Biomol. Chem. , 4 , 1038 –1048 .
52.
Cabaleiro-Lago C.
,
García-Río L.
,
Hervés P.
,
Mejuto J.C.
, and
Pérez-Juste J.
(2006 ) J. Inclu. Phenom. , 54 , 209 –216 .
53.
García-Río L.
,
Leis J.R.
,
Mejuto J.C.
, and
Pérez-Juste J.
(1997 ) J. Phys. Chem. B , 101 , 7383 –7389 .
54.
Hashimoto S.
, and
Thomas J.K.
(1985 ) J. Am. Chem. Soc. , 107 , 4655 –4662 .
55.
Castro A.
,
Leis J.R.
, and
Peña M.E.
(1989 ) J. Chem. Soc., Perkin Trans. , 2, 1861 –1866 .
56.
Fernández I.
,
García-Río L.
,
Hervés P.
,
Mejuto J.C.
,
Pérez-Juste J.
, and
Rodríguez-Dafonte P.
(2000 ) J. Phys. Org. Chem. , 13 , 664 –669 .
57.
García-Río L.
,
Leis J.R.
,
Mejuto J.C.
, and
Pérez-Juste J.
(1998 ) J. Phys. Chem. B , 102 , 4581 –4587 .
58.
Alvarez A.R.
,
García-Río L.
,
Hervés P.
,
Leis J.R.
,
Mejuto J.C.
, and
Pérez-Juste J.
(1999 ) Langmuir , 15 , 8368 –8375 .
59.
Dorrego A.B.
,
García-Río J.
,
Hervés P.
,
Leis J.R.
,
Mejuto J.C.
, and
Pérez-Juste J.
(2000 ) Angew. Chem. Int. Ed. , 39 , 2945 –2948 .
60.
Dorrego B.
,
García-Río L.
,
Hervés P.
,
Leis J.R.
,
Mejuto J.C.
, and
Pérez-Juste J.
(2002 ) J. Phys. Chem. B , 105 , 4912 –4920 .
61.
Jiang Y.B.
, and
Wang X.
(1994 ) J. Appl. Spectrosc. , 48 , 1428 –1450 .
62.
García-Río L.
,
Méndez M.
,
Paleo M.R.
, and
Sardina F.J.
(2007 ) J. Phys. Chem B , 111 , 12756 –12764 .
63.
García-Río L.
,
Leis J.R.
,
Mejuto J.C.
,
Navarro-Vázquez A.
,
Pérez-Juste J.
, and
Rodríguez-Dafonte P.
(2004 ) Langmuir , 20 , 606 –613 .
64.
García-Río L.
,
Godoy A.
, and
Leis J.R.
(2005 ) Chem. Phys. Lett. , 401 , 302 –653 .
65.
Park J.W.
, and
Song H.J.
(1989 ) J. Phys. Chem. , 93 , 6454 –6458 .
66.
Okubo T.
,
Maeda Y.
, and
Kitano H.
(1989 ) J. Phys. Chem. , 93 , 3721 –3723 .
67.
Sasaki K.J.
,
Christian S.D.
, and
Tucker E.E.
(1989 ) Fluid Phase Equilibria , 49 , 281 –289 .
68.
Tanford C.
(1980 ) The hydrophobic effect: formation of micelles and biological membranes , 2nd edn, Wiley , New York .
69.
Satake I.
,
Yoshida S.
, and
Hayakawa K.
(1986 ) Bull. Chem. Soc. Jpn. , 59 , 3991 –3993 .
70.
Jezequel D.
,
Mayaffre A.
, and
Letellier P.
(1991 ) Can. J. Chem. , 69 , 1865 –1871 .
71.
Molyneux P.
,
Rhodes C.T.
,
Swarbrick J.
(1965 ) Trans. Faraday Soc. , 61 , 1043 –1052 .
72.
Lin J.J.
, and
Somasundaran P.
(1971 ) J. Colloid Interface Sci. , 37 , 731 –752 .
73.
Junquera E.
,
Peña L.
, and
Aicart E.
(1997 ) Langmuir , 13 , 219 –224 .
74.
Cabaleiro-Lago C.
,
García-Río L.
,
Hervés P.
,
Mejuto J.C.
, and
Pérez-Juste J.
(2006 ) J. Phys. Chem. B , 110 , 15831 –15838 .
75.
Saenger W.
, and
Müller-Fahrnow A.
(2003 ) Angew. Chem. Int. Ed. , 27 , 393 –394 .
76.
Cabaleiro-Lago C.
,
García-Río L.
,
Hervés P.
, and
Pérez-Juste J.
(2009 ) J. Phys. Chem. B , 113 , 6749 –6755 .
77.
Song B.D.
, and
Jencks W.P.
(1989 ) J. Am. Chem. Soc. , 111 , 8470 –8479 .
78.
García-Río L.
,
Leis J.R.
, and
Moreira J.A.
(2000 ) J. Am. Chem. Soc. , 122 , 10325 –10334 .
79.
Cabaleiro-Lago C.
,
García-Río L.
,
Hervés P.
, and
Pérez-Juste J.
(2005 ) J. Phys. Chem. B , 109 , 22614 –22622 .
80.
Báscuas J.
,
García Río L.
, and
Leis J.R.
(2004 ) Org. Biomol. Chem. , 2 , 1186 –1193 .