The aggregartion and catalytic activity of amphiphilic calix[4]resorcinolarenes and phenols in hydrolysis of phosphonous esters in water - Dimethylformamide media

Article abstract of DOI:10.1023/A:1022118931584

The amphiphilic calix[4]resorcinolarenes, aminomethylated calix[4]resorcinolarenes, o-aminomethylphenols, and their quaternary derivatives in water - dimethylformamide media (10-75 vol.% DMF) form aggregates, which catalyze the hydrolysis of phosphonous esters. The ability to self-association and the catalytic activity of the aggregates depend on the hydrophobicity of the amphiphilic compound, the pH of solution, and the content of DMF.

Full text of DOI:10.1023/A:1022118931584

Russian Chemical Bulletin, International Edition, Vol. 51, No. 12, pp. 2183—2188, December, 2002
2183
The aggregartion and catalytic activity of amphiphilic
calix[4]resorcinolarenes and phenols in hydrolysis
of phosphonous esters in water—dimethylformamide media
ꢀ
I. S. Ryzhkina, Ya. A. Babkina, S. S. Lukashenko, K. M. Enikeev, L. A. Kudryavtseva, and A. I. Konovalov
A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan´ Research Center of the Russian Academy of Sciences,
8 ul. Akad. Arbuzova, 420088 Kazan´, Russian Federation.
Fax: +7 (8432) 75 22 53. Eꢀmail: ryzhkina@iopc.kcn.ru
The amphiphilic calix[4]resorcinolarenes, aminomethylated calix[4]resorcinolarenes,
oꢀaminomethylphenols, and their quaternary derivatives in water—dimethylformamide media
(10—75 vol.% DMF) form aggregates, which catalyze the hydrolysis of phosphonous esters.
The ability to selfꢀassociation and the catalytic activity of the aggregates depend on the hydroꢀ
phobicity of the amphiphilic compound, the pH of solution, and the content of DMF.
Key words: micelle formation, kinetics, hydrolysis, aggregates, critical micellization conꢀ
centrations, amphiphilic compounds, aminomethylated calix[4]resorcinolarenes, phenols,
phosphonic esters.
Earlier1—3 we have found that the catalytic activity of
highly organized water—organic solvent systems based on
calix[4]resorcinolarenes and their derivatives in reactions
with esters of phosphorus acids (EPA) depends mainly on
dures. The parameters of recrystallized triphenylphosphate (16)
and pꢀnitrophenol (17) corresponded to the literature values.14
The surface tension (σ) of solutions was measured on a VT
torsion balance by the ring detachment method, and electroꢀ
conductivity of solutions (χ) was estimated on a CDMꢀ2d
the kind and properties of the aggregates formed. Recently,
conductometer at 25 °C. Temperature was maintained with a
an interest to functionalized micelles sharply increased.4,5
Uꢀ1 thermostat with an accuracy of 0.1 °C. To prepare ionized
The selfꢀassembling and properties of the aggregates of
calix[4]resorcinolarenes are due1,2 to amphiphilicity, i.e.,
the presence of both a hydrophobic hydrocarbon radical
on the lower rim of the cavity of calix[4]resorcinolarenes
and a charge on the upper rim, as well as to a solvent
nature. Waterꢀsoluble calix[4]arenes (n = 4—8) containꢀ
ing the sulfonic and ammonium head groups are known
to form aggregates similarly to common ionic surfacꢀ
tants.6—8 The critical aggregation concentrations depend
on the length of the hydrocarbon radical, the number of
aromatic rings (n), and the conformation of calixarenes.
The aim of this work is a study of the aggregation of
oꢀaminomethylphenols (AMP, 1—8) and their quaterꢀ
nary derivatives (QAMP, 9, 10), calix[4]resorcinolꢀ
arene (11), and aminomethylated calix[4]resorcinolarenes
(AMC, 12—14) with different hydrophobicities in waꢀ
ter—dimethylformamide media (10—75 vol. % DMF),
and the effect of the solvent composition and the pH of
solutions on their micelleꢀforming ability and catalytic
activity in reactions with ethylꢀpꢀnitrophenyl chloroꢀ
methyl phosphonite (15).
species, the micelle formation for compounds 1—14 was studied
in the 4—8ꢀ or 1—2ꢀfold excess of NaOH or HCl for AMC or
AMP and QAMP, respectively. The reaction kinetics for these
compounds with substrate 15 was studied by spectophotometry
and 31P NMR spectroscopy under more than 10ꢀfold excess of a
nucleophile (AMP, QAMP, and AMC) with respect to subꢀ
strate 15. The reactions were monitored spectrophotometriꢀ
cally on a Specord UV—Vis spectrophotometer by the variaꢀ
tion of the absorption band of the pꢀnitrophenolate formed
(λ = 400 nm) at 25 °C and the concentration of compound 15 of
5 •10–5 mol L–1. The 31P NMR spectra were recorded on a
Bruker MSL 400 instrument (161.97 MHz, 85% H3PO4 as the
reference).
The apparent rate constants for hydrolysis (kapp) were deterꢀ
mined from the first order equation. The constants of binding of
substrates by the aggregates formed with a catalyst (Kb), the
critical aggregation concentrations (critical micellization conꢀ
centration) (CMC), and the reaction rate constants for aggreꢀ
gates (km) were calculated from the plots of kapp vs. the
nucleophile concentration. For this purpose, the known equaꢀ
tion15 was used:
kapp = (kH O + kmKbСsurf)/(1 + KbСsurf),
(1)
2
where kH O (s–1) is the rate constant for the reaction in the
Experimental
2
water—DMF system, Csurf (mol L–1) is the concentration of
AMC, AMP, or QAMP after subtraction of the CMC for these
compounds.
Compounds 1—8,9 9 and 10,10 11,11, 12—14,12 and subꢀ
strate 15 13 were synthesized according to earlier reported proceꢀ
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2026—2030, December, 2002.
1066ꢀ5285/02/5112ꢀ2183 $27.00 © 2002 Plenum Publishing Corporation

2184
Russ.Chem.Bull., Int.Ed., Vol. 51, No. 12, December, 2002
Ryzhkina et al.
Table 1. Values of CMC for AMP 2—5, 7, and 8, QAMP 9 and
10, calix[4]resorcinolarene 11 and AMC 12—14 at various рНs
(DMF (30 vol.%)—H2O)
Comꢀ
pound
CMC/mol L–1
pH 7—8
pH 3—4
pH 9—11 a
2
4
5
7
8
9
10
11
12
12b
12c
12d
13
14
4.5•10–3
3.0•10–3
1•10–3
7•10–3
2•10–3
—
5.4•10–4
1.2•10–3
4.5•10–4
—
4.5•10–4 (2•10–4
)
)
1.1•10–3 (8•10–4
3.2•10–4
—
—
—
8•10–3
1.2•10–3
—
6.0•10–4 (2.8•10–4
3.5•10–4 (3.5•10–4
)
)
—
—
1.0•10–4 (6•10–5
)
6•10–5
1•10–4
8•10–5
1•10–4
2•10–4
—
5•10–5
—
—
—
3•10–4
5•10–5
8•10–5 (2•10–5
1•10–4
8•10–5
1•10–4
9•10–4
—
)
a The CMC values calculated from the kinetic data presented in
Fig. 1 (see Table 2) are shown in parentheses.
b—d The CMC values are obtained conductometrically at the
DMF concentrations of 10,b 50,c and 75 vol.%.d
the maximal accumulation of the protonated, zwitterꢀ
ionic, and phenolate species. Compounds 1, 3, and 6
containing the Me and Bu radicals do not form aggregates
in the range of concentrations <0.1 mol L–1. Note that
compounds 7 and 8 containing two alkyl substituents at
the N atom form aggregates only in an acidic medium
(CMC = 7•10–3 and 2•10–3 mol L–1, respectively). The
CMC values for AMPs 4 and 5 containing one long alkyl
chain at the N atom are comparable to the CMC value for
R1
R2
R3
R4
R5
R6
1
2
3
4
5
6
7
8
H
Me
Me
Me
Bu
C8H17
C11H23
Bu
9
C14H29
10 C16H33
—
—
H
—
—
C9H19
C9H19
C11H23
C9H19
C9H19 Me
H
H
H
H
H
H
H
H
H
11
12
13
14
—
—
—
—
CH2NMe2
CH2NEt2
CH2NEt2
Bu
C6H13 C6H13
C9H19 C9H19
kapp•103/s–1
Results and Discussion
It is known that AMP16 and AMC2 incorporate strong
1
3.0
intramolecular hydrogen bonds (IHB) OH...N that are
responsible for the formation of zwitterionic species. These
compounds are characterized by a complicated system of
the acidꢀbase equilibria. As a consequence, the AMP can
occur in the form protonated at the N atom (рН 3—5), a
neutral or zwitterionic species (рН 6—9), and a phenolate
species (pH > 9), depending on the pH of a medium. The
zwitterionic species of AMC2 occurs in a wide pH range
of 5—10. Hence, the hydrophobized AMP and AMC are
the amphiphilic compounds capable of aggregate forꢀ
mation.
We studied by tensiometry the selfꢀassembling of
AMC, AMP, and QAMP as a function of their strucꢀ
ture and pH in the water—dimethylformamide solution
(30 vol.% DMF).5—8 Table 1 presents the CMC values of
the compounds under study at the pH values providing
2.5
2.0
1.5
2
5
1.0
0.5
0
6
3
4
5
10
15
20 Сsurf•104/mol L–1
Fig. 1. Apparent rate constants (kapp) for the reaction of subꢀ
strate 15 with compounds 12 (1), 11 (2), 4 (3), 2 (4 ), 9 (5 ), and
10 (6 ) vs. their concentrations (Csurf); DMF (30 vol.%)—H2O,
рН 10, 298 K.

Aggregation and reactivity of calixarenes
Russ.Chem.Bull., Int.Ed., Vol. 51, No. 12, December, 2002 2185
σ/dyne cm–1
factants, i.e., the CMC values decrease5,15,18 with an inꢀ
crease in the hydrocarbon radical length. Hence, the study
of the surface tension of solutions showed that the
amphiphilic AMP, QAMP, and AMC form aggregates in
aqueous DMF (30 vol.%). However, the AMCs whose
structures combine the features of both gemini surfacꢀ
tants17 and amphiphilic macrocycles5 exhibit specific beꢀ
havior that is typical of both kinds of surfactants, i.e., the
low CMC at comparatively small radical length as typical
of macrocycles and an increase in the CMC values with
the radical length as is observed for the gemini surfactants.
The study of the electroconductivity of solutions (χ)
of AMP 4 and AMC 12 as a function of their concentraꢀ
tion by a known procedure5—8 at various DMF concenꢀ
trations in aqueous solutions (Fig. 3) showed that AMP 4
forms aggregates only at the DMF concentration of 10 and
30 vol.% and AMC 12 does it at the concentrations of
10—75 vol.%. These compounds are not dissolved in waꢀ
ter and do not form micelles in DMF. The CMC values
for AMP 4 (pH 10) in binary media increase with an
increase in the DMF concentration reaching 6•10–4 and
1.2•10–3 mol L–1, respectively. The CMC values for AMC
12 (pH 11) somewhat decrease (to ∼50 vol.% DMF) and
slightly depend on the pH of solutions (see Table 1,
Figs. 3 and 4). In all cases, this compound likely exists in
one ionized form, namely, as a zwitterion, as has been
shown in the study reported earlier.2
To compare the micelleꢀforming ability of both comꢀ
mon surfactants and amphiphilic AMC and AMP, we
measured σ and χ of solutions of the cationic surfactant,
cetyltrimethylammonium bromide (CTAB), anionic surꢀ
factant sodium dodecylsulfate (SDS), and nonꢀionic surꢀ
factant TritonꢀXꢀ100 as functions of their concentraꢀ
tions in the binary solvent water—DMF in the range of
10—75 vol.%. Figure 4 presents the CMC values for
CTAB, SDS, TritonꢀXꢀ100, and AMC 12 vs. the DMF
concentration. These dependences for ionic surfactants,
CTAB and SDS, are extremal similarly to a variation19 in
60
55
1
50
3
2
45
40
4
10
20
30
Сsurf•10–5/mol L–1
Fig. 2. Variation of the surface tension of the systems as a funcꢀ
tion of the concentrations of calix[4]resorcinolarene 11 (1), AMC
12 (2), AMP 4 (3), and QAMP 10 (4); DMF (30 vol.%)—Н2О.
AMP 2 with a similar radical in the benzene ring. Thus,
the number of the alkyl substituents affects substantially
the micelle formation of the amphiphilic AMP. The CMC
values for QAMPs 9 and 10, containing a fragment of
cationic surfactants, and those for the hydrophobized
AMPs 2, 4, and 5 slightly differ from each other (see
Table 1). However, QAMPs decrease the surface tension
(σ) of solutions more sharply than AMPs (Fig. 2). Note
that the anion and zwitterionic species of AMP form agꢀ
gregates easier than the cation species (see Table 1).
The CMC values found for AMCs 12 and 14 (R6 =
C9H19) are nearly one order in magnitude lower than
those for AMP 2 (R1 = C9H19) at close pH values. The
CMC values for AMC 13 and AMP 5 (R1 = R6 = C11H23)
are of the same order. The higher CMC values for AMC
13 are likely due to less favorable hydrophilicꢀlypophilic
balance compared to AMCs 12 and 14 similarly to the
situation observed for gemini surfactants.17 Contrary to
this, AMP and QAMP behave similarly to common surꢀ
χ/µS cm–1
3
Table 2. Parameters of the reaction of substrate 15
with AMPs 2 and 4, QAMPs 9 and 10, calix[4]resorꢀ
cinolarene 11, and AMC 12
100
80
2
1
Comꢀ
pound
CMC•104
/mol L–1
km•103
/s–1
Kb
/L mol–1
60
40
20
2
4
9
10
11
12
2
8
2.8
2.7
0.6
0.2
0.52
0.78
2.6
0.95
1.7
210
180
100
170
2120
1570
0
0.2
0.6
1.0
Сsurf•10–3/mol L–1
4.4
Fig. 3. Electroconductivity (χ) of the systems as a function of the
concentrations of AMC 12 (1, 2) and AMP 4 (3) at the DMF
concentrations of 10 (1, 3) and 75 vol.% (2).
Note. The reaction conditions: pH 10, 25 °C, DMF
(30 vol.%)—H2O.

2186
Russ.Chem.Bull., Int.Ed., Vol. 51, No. 12, December, 2002
Ryzhkina et al.
CMC•10–n/mol L–1
concentration up to ∼50 vol.% can indicate the inclusion
of the solvent molecules in the aggregate structure.
Difference in the behavior of the AMC aggregates was
also found in the study of the effect of the additives of
10
8
4
triphenylphosphate (16) and pꢀnitrophenol (17) (C16,17
=
1•10–4 mol L–1), which simulate the interaction of the
EPA with micelles in the course of chemical reaction, on
the selfꢀassembling of AMC 14, AMP 4, and TritonꢀXꢀ100
in the 30% aqueous DMF. Additional inflection points
appear on the plots of the surface tension vs. the concenꢀ
trations of AMP or TritonꢀXꢀ100 (CMCꢀ2), which point
to micellar transitions, i.e., the formation of different
kinds of micelles;22 CMCꢀ1 decreases in these sysꢀ
tems by 3—4 times and become equal to 4•10–4 and
4•10–5 mol L–1, respectively (Fig. 5). The effect of comꢀ
pounds 16 and 17 on aggregation in these systems is the
same and does not influence the AMC aggregation in fact
(see Fig. 5); CMC in the systems remains unchanged.
Earlier we have shown by the 31Р NMR that AMP and
AMC in the waterꢀalcohol and micellar solutions of surꢀ
factants catalyze the hydrolysis of EPAs. In particular, the
interaction of AMP23 and AMC2,3 with pꢀnitrophenylꢀ
diphenyl phosphate occurs in two stages: in the first stage,
phosphorylated AMP or AMC are formed, which are furꢀ
ther hydrolyzed to the corresponding acids in the slower
stage. A drop in the intensity of the substrate signal in the
31Р NMR spectra is observed. The drop is accompanied
by the appearance of the signal of phosphorylated interꢀ
mediate, whose intensity initially increases and then deꢀ
creases. Simultaneously, the signal of the acid arises and
its intensity increases in time.
1
3
6
4
2
2
20
40
60
[DMF] (vol.%)
Fig. 4. Variation in CMC of CTAB (1, n = 3), SDS (2, n = 2),
TritonꢀХꢀ100 (3, n = 4), and AMC 12 (4, n = 5) with the DMF
concentration.
viscosity in the water—DMF system. Like urea, DMF is
an organic additive that increases the CMC of aqueous
solutions of surfactants due to changes in the hydrogenꢀ
bonded structure of water.18,20 At the same time, as can
be seen in Fig. 4, the CMC of the nonꢀionic surfactant
TritonꢀXꢀ100 decreases by almost one order of magniꢀ
tude with an increase in the DMF concentration. The
stabilization of the micellar state in this case can be exꢀ
plained by inclusion of the DMF molecules, similarly to
urea,18 into the micelle of TritonꢀXꢀ100. Comparison of
the CMC for both common surfactants and AMC (see
Fig. 4) gives evidence of the high ability of the latters to
selfꢀassembling: the CMC for AMC 12 (5•10–5—1•10–4
mol L–1) are considerably lower than those for CTAB and
SDS, which alter with the DMF concentration in the
regions of (2—8)•10–3 and (1—3)•10–2 mol L–1, reꢀ
spectively. As was mentioned above, low CMC values
(1•10–4—5•10–6 mol L–1) are typical of amphiphilic
macrocyclic compounds.5 In addition, contrary to comꢀ
mon surfactants, the CMC for AMC are independent in
fact of the viscosity of the binary mixture water—DMF.
This can indicate the higher viscosity of the AMC aggreꢀ
gates compared to micelles of common surfactants and
agrees with the data obtained7 in the study of the micelle
formation in waterꢀsoluble calix[6]arenes, as well as the
different structure of the aggregates. It has been shown for
the AMC aggregates,7 that the lyotropic liquidꢀcrystal
structures are formed from the bilayers as precursors in
the CMC region, whereas common surfactants form
spherical micelles in the CMC region.21 A trend to the
CMC lowering for AMC 12 with an increase in the DMF
σ/dyne cm–1
70
65
60
4
55
3
50
1
45
2
0.0002
0.0004
0.0006 Сsurf/mol L–1
Fig. 5. Variation of the surface tension (σ) of the systems as a
function of the concentrations of AMC 14 (1, 2), AMP 4 (3),
and TritonꢀХꢀ100 (4) in the absence (1) and in the presꢀ
ence (2—4) of compound 16; С16 = 1•10–4 mol L–1, DMF
(30 vol.%)—Н2О.

Aggregation and reactivity of calixarenes
Russ.Chem.Bull., Int.Ed., Vol. 51, No. 12, December, 2002 2187
I (rel. units)
strate 15 with the compounds under study, namely, CMC,
Kb, and km. As follows from the comparison of the CMC
values obtained by tensiometry, conductometry, and the
kinetic method (see Tables 1 and 2), they are lower in the
latter case. This is likely due to the effect of the substrate
additives on the micellar system. The reactivities of funcꢀ
tional aggregates formed by calix[4]resorcinolarenes,
AMP, and QAMP, which hydrolize 15 via different
mechanisms, differ dramatically (see Fig. 1 and Table 2).
The CMC of the aggregates of calix[4]resorcinolarenes is
one order of magnitude lower and Kb is one order of
magnitude higher than those for AMP.
10
8
1
6
4
3
2
2
Hence, the aggregates of macrocyclic amphiphiles,
calix[4]resorcinolarenes containing hydroxy and amino
groups, are formed much more easily and bind substrates
more strongly than the aggregates of oꢀaminomethylꢀ
phenols; they exhibit much higher hydrolytic activity at
low concentrations.
10
20
30
40
50
τ/min
Fig. 6. Variation of the intensities of the 31Р NMR spectra at
δ 17.6 (1), 16.6 (2), and 13.6 (3) in the course of the reaction of
QAMP 9 (4•10–2 mol L–1) with substrate 15 (4•10–3 mol L–1
at рН 8 and temperature 311 К; DMF (30 vol.%)—Н2О.
)
This work was supported by the Russian Foundation
for Basic Research (Projects 00ꢀ03ꢀ32119 and №02ꢀ03ꢀ
06512).
The 31P NMR study of the reaction of 15 with nonꢀ
micelleꢀforming AMP 6 and micelleꢀforming AMP 4,
QAMP 9, and AMC 13 in the 30% aqueous DMF showed
that the EPA hydrolysis in the micellar systems based on
AMP, QAMP, and AMC occurs likely through different
mechanisms. Irrespectively of the aggregation state, AMPs
interact with substrate 15 (δ 17.3 ppm) via the above
mechanism to form phosphorylated AMP (δ 16.6), folꢀ
lowed by its hydrolysis to the acid (δ 13.3). The examinaꢀ
tion of the 31P NMR spectra of the reaction mixtures of
15 with QAMP (Fig. 6) recorded at different reaction
times showed that the interaction occurs simultaneously
through two pathways, i.e., the transesterification and hyꢀ
drolysis of the substrate occur in parallel. The hydrolysis
of compound 15 in the presence of AMC 12 is not acꢀ
companied by the formation of an intermediate. The difꢀ
ference in the reaction mechanisms of compound 15 with
AMP and AMC is likely due to the fact that the phosphoꢀ
rylation of the macrocyclic phenols AMCs proceeds more
slowly than that of simple phenols.24 The substrate bound
by the AMC aggregate is hydrolyzed faster than it underꢀ
goes transesterification.
The spectrophotometric study of the reaction kinetics
for substrate 15 with calix[4]resorcinolarene 11, AMC 12,
AMPs 2 and 4, and QAMPs 9 and 10 confirmed the
formation of aggregates of these compounds, namely, the
kinetic curves have a "saturation" shape that is typical of
micelleꢀcatalyzed reactions15 (see Fig. 1). A similar plot
of kapp against the concentration of the nonꢀmicelleꢀformꢀ
ing AMP 3 is linear, and the bimolecular rate constant for
this reaction is 0.2 L mol–1 s–1. Table 2 presents the
parameters of the micelleꢀcatalyzed reaction of subꢀ
References
1. I. S. Ryzhkina, L. A. Kudryavtseva, A. R. Burilov, E. Kh.
Kazakova, and A. I. Konovalov, Izv. Akad. Nauk, Ser. Khim.,
1998, 275 [Russ. Chem. Bull., 1998, 47, 269 (Engl. Transl.)].
2. I. S. Ryzhkina, L. A. Kudryavtseva, A. R. Mustafina, Yu. E.
Morozova, E. Kh. Kazakova, K. M. Enikeev, and A. I.
Konovalov, Izv. Akad. Nauk, Ser. Khim., 1999, 456 [Russ.
Chem. Bull., 1999, 48, 453 (Engl. Transl.)].
3. I. S. Ryzhkina, L. A. Kudryavtseva, Ya. A. Babkina, K. M.
Enikeev, M. A. Pudovik, and A. I. Konovalov, Izv. Akad.
Nauk, Ser. Khim., 2000, 1361 [Russ. Chem. Bull., Int. Ed.,
2000, 49, 1355].
4. R. Jairam, P. G. Potvin, and S. Balsky, J. Chem. Soc., Perkin
Trans. 2,1999, 363.
5. A. D. Pidwell, S. R. Collinson, S. J. Coles, M. B. Harsthouse,
M. Schroder, and D. W. Bruce, Chem. Commun., 2000, 955.
6. S. Arimori, T. Nagasaki, and S. Shinkai, J. Chem. Soc.,
Perkin Trans. 2, 1995, 679.
7. S. Shinkai, T. Arimura, K. Araki, and H. Kawabata, J. Chem.
Soc., Perkin Trans. 1, 1989, 2039.
8. S. Shinkai, in Calixarenes, a Versalite Class of Macrocyclic
Compounds, Eds. J. Vicens and V. Bohmer, Kluwer,
Dordrecht, 1990, 173.
9. B. Reichert, Die MannichꢀReaktion, SpringerꢀVerlag, Berꢀ
lin—Göttingen—Heidelberg, 1959, 192 p.
10. E. P. Tishkova, L. A. Kudryavtseva, L. Ya. Zakharova, and
S. B. Fedorov, Izv. Akad. Nauk, Ser. Fiz., 1996, 60, № 4, 109
[Russ. Phys. Bull., 1996, 60, No. 4 (Engl. Transl.)].
11. L. M. Tunstad, J. A. Tucker, E. Dalcanale, J. Wieser, J. A.
Byant, J. C. Sherman, R. C. Helgeson, C. B. Knober, and
D. J. Cram, J. Org. Chem., 1989, 54, 1305.
12. Y. Matsuskita and T. Matsui, Tetrahedron Lett., 1993,
34, 7433.

2188
Russ.Chem.Bull., Int.Ed., Vol. 51, No. 12, December, 2002
Ryzhkina et al.
13. V. E. Bel´skii, L. A. Kudryavtseva, O. M. Il´ina, and B. E.
Ivanov, Zh. Obshch. Khim., 1979, 49, 2470 [J. Gen. Chem.,
1979, 49 (Engl. Transl.)].
21. A. I. Rusanov, Zh. Vsesoyuz. khim. oꢀva im. D. I. Mendeleeva,
1989, 174 [Mendeleev Chem. J., 1989, No. 2 (Engl. Transl.)].
22. A. I. Serdyuk and R. V. Kucher, Mitsellyarnye perekhody v
rastvorakh poverkhnostnoꢀaktivnykh veshchestv [Micellar
Transitions in Solutions of Surfactants], Naukova Dumka,
Kiev, 1987, 208 pp. (in Russian).
23. I. S. Ryzhkina, L. A. Kudryavtseva, K. M. Enikeev, V. I.
Morozov, G. A. Boos, and Yu. I. Sal´nikov, Izv. Akad. Nauk,
Ser. Khim., 2000, 1355 [Russ. Chem. Bull., Int. Ed., 2000,
49, 1349].
24. E. P. Zhil´tsova, L. A. Kudryavtseva, A. P. Timosheva, N. I.
Bashmakova, A. V. Chernova, and A. I. Konovalov, Elektroꢀ
khimicheskie, opticheskie i kineticheskie metody v khimii.
Sbornik trudov, posvyashchennyi yubileyu professora V. F.
Toropovoi [Electrochemical, Optic, and Kinetic Methods in
Chemistry. Collected Reports to the Anniversary of Prof. V. F.
Toropova], KGU, Kazan´, 2000, 145 pp. (in Russian).
14. Svoistva organicheskikh soedinenii. Spravochnik [Properties of
Organic Compouinds. Handbook], Ed. A. A. Potekhin,
Khimiya, Leningrad, 1984, 520 pp. (in Russian).
15. E. Fendler and J. Fendler, in Advances in Physical Organic
Chemistry, Ed. V. Gold, Academic Press, London, 1970, 8.
16. R. A. Shagidullina, I. S. Ryzhkina, A. B. Mirgorodskaya,
L. A. Kudryavtseva, V. E. Bel´skii, and B. E. Ivanov, Izv.
Akad. Nauk, Ser. Khim., 1994, 1215 [Russ. Chem. Bull., 1994,
43, 1149 (Engl. Transl.)].
17. F. M. Menger and V. A. Migulin, J. Org. Chem., 1999,
64, 8916.
18. J. E. Gordon, The Organic Chemistry of Elecrtolyte Solutions,
A Wiley—Interscience—J. Wiley and Sons, New York, 1975.
19. W. P. Jencks, Catalysis in Chemistry and Enzymology,
McGrauꢀHill Book Company, New York, 1969.
20. S. B. Sulthana, S. G. T. Bhat, and A. K. Rakshit, Bull.
Chem. Soc. Jpn., 2000, 73, 281.
Received December 14, 2001;
in revised form April 9, 2002