Inverse micellar catalysis of phosphorylation of hydroxybenzylated polyethylenimines

Article abstract of DOI:10.1007/s11176-005-0474-9

The aggregation in polyethylenimine-chloroform and cetyltrimethylammonium bromide-polyethylenimine-chloroform systems is studied by dielcometric titration. Inverse micelles of cetyltrimethylammonium bromide catalyze the phosphorylation of hydroxybenzylate

Full text of DOI:10.1007/s11176-005-0474-9

Russian Journal of General Chemistry, Vol. 75, No. 10, 2005, pp. 1603 1609. Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 10, 2005,
pp. 1681 1687.
Original Russian Text Copyright
2005 by Zhil’tsova, Kudryavtseva, Gainanova, Timosheva, Lukashenko, Konovalov.
Inverse Micellar Catalysis of Phosphorylation
of Hydroxybenzylated Polyethylenimines
E. P. Zhil’tsova, L. A. Kudryavtseva, G. A. Gainanova,
A. P. Timosheva, S. S. Lukashenko, and A. I. Konovalov
Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center,
Russian Academy of Sciences, Kazan, Tatarstan, Russia
Received October 18, 2004
Abstract The aggregation in polyethylenimine chloroform and cetyltrimethylammonium bromide poly-
ethylenimine chloroform systems is studied by dielcometric titration. Inverse micelles of cetyltrimethyl-
ammonium bromide catalyze the phosphorylation of hydroxybenzylated polyethylenimines in chloroform.
The dependence of parameters of the micelle-catalyzed reaction on the structure and concentration of poly-
ethylenimine and on the reaction temperature is studied. The inverse micelles affect the complexation of
polyethylenimines with 4-nitrophenol.
An interest in systems based on polymers and sur-
factants is caused by their practical and theoretic
importance. These systems are used in production of
detergents, in cosmetic industry, and in the regenera-
tion of oils. Furthermore, polymer-micellar solutions
can serve as models of biological binding with the
participation of biomembranes [1]. As a rule, studies
in the field of polymer colloid solutions concern the
nature and structure of the associates. It was found
that the polymer micelle interaction depends on the
structure of the polymer and on the chemical nature,
geometry, and charge of the surfactant [1]. The pres-
ence of polymers in micellar solutions may affect the
characteristics of micellar systems (critical micelliza-
tion concentration, aggregation number, shape of
aggregates), as well as the solubilizing power of
micelles [1, 2]. At the same time, it is poorly under-
stood how the formation of the polymer micelle
complex affects the reactivity of the polymer. Pub-
lished papers in this field, as a rule, deal with aqueous
solutions. For example, the effect of stuctural and
concentration factors on the hydrolysis of phosphorus
acid esters in the cationic surfactant polyethylen-
imine water system was examined in [3 7]. The
dependence of the catalytic activity of the polymer
colloid complexes on their size, shape, and structure
was revealed [7].
relative content of surfactant and polyethylenimine in
solution [3].
In this study we examined the effect of inverse
micelles of a cationic surfactant, cetyltrimethyl-
ammonium bromide I, in chloroform on the reaction
of 4-nitrophenyl bis(chloromethyl)phosphinate II with
branched polyethylenimines III VI containing
o-hydroxybenzyl substituents at the tertiary and
secondary nitrogen atoms.
CH CH N
CH2CH2NH
CH2R
R = C H OH-o (III), C H (OH-o)(i-C H -p) (IV VI).
2
2
CH R
2
6
4
6
3
9 19
The mean molecular mass of the monomeric unit
of hydroxybenzylated polyethylenimines III VI was
8
8, 77, 88, and 125, respectively. An increase in the
molecular mass of the monomeric unit in the series
IV VI is indicative of an increase in the degree of
substitution of the polymers. On the average, in IV
VI there was 0.12, 0.16, and 0.3 hydroxybenzylated
fragment per unsubstituted monomeric fragment. The
degree of substitution in III was 0.3. In alkylated
polyethylenimine VII used for comparison and
containing fragments A and B shown below, the
molecular mass of the monomeric unit was 150, and
the degree of substitution was 0.45.
CH CH N
CH2CH2NHC14H29
2
2
Our previous studies of phosphorylation of al-
kylated polyethylenimine in toluene micellar solutions
of poly(ethylene glycol)-600 monolaurate showed that
inverse micelles of a nonionic surfactant may both
catalyze and inhibit this process, depending on the
C H
14 29
A
B
Micelle-forming properties of compound I in
chloroform were studied previously by dielcometric
1
070-3632/05/7510-1603 2005 Pleiades Publishing, Inc.

1604
ZHIL’TSOVA et al.
ethylenimines III VI is characterized by the signals
6
5
0
0
at 22.7, 22.9, 22.3, and 23.9 ppm, respectively. The
product of phosphorylation of alkylated polyethyl-
enimine VII containing no OH groups gives in
chloroform the signal in the same range, 23.7 ppm.
These facts indicate that compounds III VI are
phosphorylated at NH groups, with the formation of
products VIII XI, respectively.
4
3
0
0
NH + (ClCH ) P(O)OC H NO -p
2
2
6
4
2
III VI
II
2
p-NO C H OH + NP(O)(CH Cl) .
2
6
4
2
2
VIII XI
3
2
0
0
In the absence of surfactant I, the dependence of
1
the observed rate constant (k ) of the reaction of poly-
o
1
ethylenimines III VI with phosphinate II on the
concentration of the nucleophile is linear (Fig. 2) and
is described by the following equation:
0
0.5
1.0
1.5
2.0
CI 10 , M
2.5
2
Fig. 1. Orientational polarization of cetyltrimethyl-
ammonium bromide solitions in chloroform (1) in the
absence and (2, 3) in the presence of polyethylenimines
ko,0 = k2,0CPEI
.
For III VI at 25 C, k 0.85, 0.16, 0.33, and
2
,0
1
1
(
2) III and (3) V; 20 C, C
0.01 M.
0.66 l mol s , respectively. The value of k for III
PEI
2,0
is somewhat higher than for hydrophobized compound
VI with the same degree of substitution. This is
evidently associated with the unfavorable steric effect
of hydrocarbon radicals of VI. In the series of com-
pounds IV VI, the relative content of the reactive
titration and the kinetic method [8]. Formation of
micellar aggregates of I in chloroform at 20 50 C
proceeds in the concentration range 0.003 0.015 M.
The aggregation behavior of I in the presence of poly-
ethylenimines was studied by the dielcometric method. N H groups decreases, which should cause a decrease
Figure 1 shows the concentration dependence of the
orientational polarization (Por,exp) of solutions of I in
the absence and in the presence of III and V. In all
the cases, in the initial part of the curve an increase in
the concentration of I causes a decrease in the orienta-
tional polarization, which is followed by a flat
minimum in the concentration range 0.003 0.005 M
and certain increase beginning from the concentration
of 0.012 M. Such a pattern, according to [9], is attri-
butable to the formation of micellar aggregates and
reconstruction of their structure at higher concentra-
tions of the surfactant.
in the observed rate constants of the process. However,
actually k2,0 increases, which may be caused by the
self-association; its occurrence is confirmed by di-
elcometric titration. The concentration dependences
of the dielectric permittivity of solutions of III VI
in chloroform contain the clearly and weakly pro-
nounced inflections (Fig. 3, Table 1). Inflections of
the first type are caused by deceleration of the growth
of and flattening-out of the dependence. Inflections
of the second type are associated with a sharp increase
in the dielectric permittivity at a high content of the
polymers in solutions. According to [9], inflections
of the first type may be caused by the appearance of
symmetric sites due to self-association of polyethylen-
imines through intramolecular interactions in the
polymeric chain. The presence of two inflections in
the range of low concentrations of III and IV
(Fig. 3) suggests the possibility of formation of asso-
ciated structures of different types in solution. In-
crease in the concentration of the polymer favors the
appearance of supramolecular associates due to the
intermolecular hydrogen bonding and dipole dipole
interactions. Formation of large and apparently un-
symmertical aggregates should make the system as a
whole more asymmetric, causing an increase in the
Inverse micelles of I formed in chloroform affect
the reactivity of polyethylenimines toward phos-
phorus acid esters. The mechanism of nucleophilic
substitution was studied by UV and 31P NMR spec-
troscopy. Elimination of 4-nitrophenol, detected spec-
trophotometrically in the reactions of III VI with
phosphinate II, suggests the formation of phospho-
rylated polyethylenimines. However, polymers III VI
contain two functional groups, NH and phenolic
hydroxyl, reactive toward II, and the reaction may
3
1
occur at both reaction centers. P NMR data show
that the product formed by phosphorylation of poly-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 10 2005

INVERSE MICELLAR CATALYSIS OF PHOSPHORYLATION
1605
CPEI, M
ko,S = k2,SCPEI.
0
0.02 0.04 0.06 0.08
4
4
.5
.0
6
5
4
The values of k2,S for III and V at 25 C and
.025 M concentration of I are 1.3 and 0.6 l mol s ,
1
1
0
8
3
and at 0.25 M concentration of I, 2.0 and
1
1
0
.94 l mol s , respectively.
3
3
.5
.0
Figure 4 shows the dependence of the observed rate
constant of phosphorylation of III VI on the con-
centration of I. An increase in the content of cetyltri-
methylammonium bromide in solution is accompanied
by an increase in the rate constant of the process. A
specific feature of the concentration dependences
1
2
2
.5
.0
2
3
2
7
6
1
1
.5
.0
5
4
(
Fig. 4) is their tendency to flatten out (in the sur-
factant concentration range 0.05 0.1 M) followed by
an increase in the observed rate constant. We observed
previously the latter trend in nucleophilic substitution
in four-coordinate phosphorus acid esters in micellar
solutions in nonaqueos media [10] and attributed it to
the possible rearrangement of the structure of nano-
aggregates.
1
0
0
.5
0
0
.01 0.02 0.03 0.04
CPEI, M
Fig. 2. Observed rate constant of the reaction of poly-
ethylenimines (1 3) III, (4) IV, (5 7) V, and (8) VI with
phosphinate II in chloroform (1, 4, 5, 8) in the absence
and (2, 3, 6, 7) in the presence of surfactant I as a
function of the concentration of polyethylenimines;
Treatment of the concentration dependences (Fig.
) at [I] < 0.15 M using the equation given below,
4
corresponding to the pseudophase model of micellar
catalysis [11], allowed us to calculate the parameters
of the micelle-catalyzed reaction (Table 2).
2
5 C, C , M: (1, 4, 5, 8) 0, (2, 6) 0.025, and (3, 7) 0.25.
I
effective values of the dielectric permittivity of the
solutions.
k K C + k
0
m
b
S
ko =
.
1
+ K C
b S
In micellar solutions of cetyltrimethylammonium
bromide, the dependence of the rate constant on the
polyethylenimine concentration remains linear (Fig. 2)
and is described by the following equation:
Here k and k are the rate constants of the reactions
in the micellar phase and in the bulk of the solvent,
m
0
respectively; K , constant of binding of the substrate
b
log CPEI
3.5
5
.0
4.5
4.0
3.0
2.5
2.0
4
4
4
.830
.825
.820
4
.92
.90
.88
.86
.84
4
4
4
3
1
4
4
4
.815
.810
4
4
4
.82
2
.80
5
4.805
1.5
.0
4.5
4.0
3.5
3.0
log CPEI
2.5
2.0
Fig. 3. Dielectric permittivity of solutions of (1) III, (2) IV, (3) V, and (4) VI in chloroform as a function of the logarithm of
polyethyleneimine concentration at 20 C.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 10 2005

1606
ZHIL’TSOVA et al.
Table 1. Critical association concentrations corresponding
to the inflections of the first and second types in the
concentrational dependences of the dielectric permittivity
of solutions of III IV at 20 C
Table 2. Parameters of the reaction of polyethylenimines
III VI with phosphinate II in chloroform, catalyzed by
micelles of cetyltrimethylammonium bromide
Comp.
no.
PEI,
M
T,
C
km 102, K , CMC 103,
b
s 1
l mol
1
M
Critical association concentration, M
Comp. no.
type I inflections
type II inflections
III
III
III
III
IV
V
0.01
0.01
0.01
0.002
0.01
0.01
0.002
0.01
25
40
50
25
25
25
25
25
1.5
2.7
3.6
0.4
0.3
0.87
0.16
1.1
54
24
17
66
186
90
4.1
7.6
8.0
4.5
2.9
2.5
8.8
6.3
5
3
5 10 3
III
IV
V
7 10 , 1.2 10
5
4
6 10 3
6.2 10 , 8 10
10 4
8 10 3
V
VI
67
49
VI
2 10 4
4 10 3 10 2
with the surfactant micelles, C , concentration of I in
solution minus critical micellization concentration
binding of phosphinate II with micelles. Variation of
the content of polyethylenimine III only slightly af-
fects the micellization of cetyltrimethylammonium
bromide. With an increase in the concentration of
polyethylenimine V the critical micellization con-
centration of I decreases.
S
(
CMC).
Table 2 shows that the rate constant in the micellar
phase increases with the growth of the concentration
of polyethylenimines and the reaction temperature.
The constant of binding of substrates with micelles
decreases with the growth of temperature and slightly
depends on the concentration of polyethylenimines.
Increase of the relative content of hydroxybenzyl
substituents in the series of compounds IV VI leads
to an increase in the rate constant of the reaction in
the micellar phase and to a decrease in the constant of
Binding of polyethylenimines with inverse mi-
celles of cationic surfactant I alters not only their re-
activity, but also their complexing power toward
4
-nitrophenol released by the nucleophilic substitution.
Polyethylenimine forms a complex with 4-nitrophenol
owing to the presence of NH groups in the polymer
molecules. With an increase in the polymer concentra-
tion, the UV absorption band decreases in the inten-
sity, and an absorption band appears in the visible
range (Tables 3, 4). According to [12], this fact sug-
gests the appearance in solution of hydrogen-bonded
ion pair XIII along with free p-nitrophenol and
hydrogen-bonded complex XII, with these species
occurring in an equilibrium.
7
6
4
5
4
3
2
3
2
p-NO2C6H4OH + NR3
p-NO C H OH NR3
2 6 4
+
p-NO C H O H N R3
2
6
4
XIII
8
7
1
0
5
It is known that the position of this equilibrium
depends on the polarity of the medium [12]. In sol-
vents with a low dielectric permittivity, it is shifted
toward formation of the nonionic structure. This fact
may be used for estimating the polarity of the micro-
surrounding of these molecules. In micellar solutions
of cetyltrimethylammonium bromide in chloroform,
4-nitrophenol as well as its complex with polyethylen-
imine are bound with the micelles of I. This is con-
firmed by the bathochromic shift of the absorption
band of 4-nitrophenol and hydrogen-bonded complex
1
6
0.2
0.4
0.6
CI, M
Fig. 4. Observed rate constant of the reaction of poly-
ethylenimines (1 4) III, (5) IV, (6, 7) V, and (8) VI with
phosphinate II as a function of the concentration of I at
(
1, 2, 5 8) 25, (3) 40, and (4) 50 C. Concentration of
polyethylenimines, M: (1, 6) 0.002 and (2 5, 7, 8) 0.01.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 10 2005

INVERSE MICELLAR CATALYSIS OF PHOSPHORYLATION
1607
Table 3. Optical density of the absorption bands of the
polyethylenimine III or IV 4-nitrophenol complex in
Table 4. Optical density of the absorption bands of the
polyethylenimine V 4-nitrophenol complex in the micellar
solutions of surfactant I in chloroform; 25 C, d 1 cm,
chloroform; 25 C, d 1 cm, 4-nitrophenol concentration
5
4-nitrophenol concentration 5 10 5
M
5
10
M
CIII, M D310 nm D400 nm CV, M D322.6 nm D410 nm
CI 0.025 M
CV, M
CI 0.25 M
0
0
0
0
0
0
0
0
0
0.51
0
0
0.451
0.249
0.224
0.171
0.182
0.163
0.123
0.106
0.098
0
0.5
D322.6 nm D424 nm
D322.6 nm
D430 nm
.0005
.001
.002
.005
.01
.015
.02
.03
0.459
0.396
0.358
0.293
0.253
0.23
0.161
0.278
0.397
0.5
0.597
0.627
0.648
0.701
0.002
0.005
0.01
0.015
0.02
0.03
0.04
0.05
0.613
0.671
0.691
0.708
0.744
0.774
0.82
0
0
0
0
0
0.54
0
0.56
0
.0025
.005
.01
0.084
0.081
0.066
0.067
0.053
1.004
1.09
1.09
1.07
1.04
0.085
0.075
0.076
0.077
0.076
1.16
1.22
1.22
1.24
1.26
.02
0.219
0.208
0.028
XII in the UV range of the spectrum and still greater
shift of the absorption band in the visible range,
belonging to ion pair XIII formed by p-nitrophenolate
anion and protonated polyethylenimine (Table 5).
Also, an increase in the concentration of I in chloro-
form leads to a decrease in the optical density of the
absorption band of the complexes of polyethyleni-
mines III and V with 4-nitrophenol in the UV part of
the spectrum and to increase in the intensity of bands
in the visible range (Fig. 5). This fact indicates that,
in the polymer micelle complex, the NH groups of
polyethylenimine molecules are in a more polar micro-
surrounding, i.e., in the nuclei of the inverse micelles
of the cationic surfactant.
branched polyethylenimine (M 10000) with tetradecyl
bromide according to [14]. The sample of starting
polyethylenimine (Aldrich) was used without addi-
tional purification. The mean molecular mass of
monomeric units of polyethylenimines was evaluated
by potentiometric titration [15]. The molecular mass
of the monomeric unit of the starting unsubstituted
polymer was 69. Chloroform was purified before use
by a standard procedure [16].
D
.2
5
6
1
1
.0
Thus, the data obtained show that the binding of
polyethylenimines with the inverse micelles of a
cationic surfactant affects their reactivity and com-
plexing properties. The extent and character of this
effect depend on the content of surfactant in solution
and on the structure and concentration of the poly-
ethylenimine.
0.8
0
0
0
.6
.4
.2
1
EXPERIMENTAL
4
3
2
Cetyltrimethylammonium bromide (Sigma) was
purified by crystallization from acetone ethanol
mixture. 4-Nitrophenyl bis(chloromethyl)phosphinate
was prepared according to [13]. Compounds III VI
were prepared from branched polyethylenimine (M
0
0
0.05
0.10
0.15
0.20
CI, M
Fig. 5. Optical densities of the absorption bands of
4-nitrophenol at (1) 322.6 and (2) 400 nm and in the
absorption maxima of 4-nitrophenol in the presence of
polyethylenimines (3, 5) III and (4, 6) V in micellar
solutions of surfactant I in chloroform in the (3, 4) UV
and (5, 6) visible ranges, as functions of the concentra-
tion of I; 25 C, d 1 cm; (1 6) 4-nitrophenol concentra-
tion 5 10
enimines 0.002 M.
1
0000) and o-dimethylaminomethylphenol or o-di-
methylaminomethyl(p-isononyl)phenol (amine inter-
change) by refluxing for 5 10 h in p-xylene in the
presence of a catalytic amount of p-toluenesulfonic
acid with the subsequent removal of volatile products
and keeping in a vacuum at 150 C to constant weight.
Compound VII was prepared by the reaction of
5
M, (3 6) concentration of polyethyl-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 10 2005

1608
ZHIL’TSOVA et al.
Table 5. Positions of the band maxima in the absorption
spectra of 4-nitrophenol and 4-nitrophenol polyethyleni-
mine III, V complex in the micellar solutions of surfactant
controlled capacitor [18]. The refractive indices were
measured on an IRF-23 refractometer.
I in chloroform; 25 C, 4-nitrophenol concentration 5
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1
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-nitrophenol
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0
0
0
0
0
0
0
0
0
310
312
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400
412
415
418
420
425
427
428
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. Zhil’tsova, E.P., Kudryavtseva, L.A., Lukashen-
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5
1
0
M. The concentration of polyethylenimines III
VI (M) was calculated from the molecular weight of
the monomeric unit.
9
. Zhil’tsova, E.P., Timosheva, A.P., Shagidullina, R.A.,
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MSL-400 spectrometer (162 MHz). Phosphinate II in
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concentration of substrate II was 0.02 M; that of III,
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Dielcometric titration was carried out according to
[
17]. The orientational polarization was calculated
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1970, vol. 8, p. 271.
1
2. Zeegers-Huyskens, T. and Huyskens, P., Molecular
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Eds., Chichester: Wiley, 1980. Translated under the
title Molekulyarnye vzaimodeistviya, Moscow: Mir,
Por,exp = 3 10 C 1[( 12
3
+ 2)2
1)/(
1
2
2
2
(
n
n )/(n + 2)],
1 1
1
2
1
984, vol. 2, p. 62.
where C is the solute concentration, M; , dietectric
permittivity; n, refractive index; indices 12 and 1 refer
to the solution and solvent, respectively. The dielec-
tric permittivity of solvents was measured on an in-
stallation consisting of an E12-1 device operating in
the beat mode and a measuring cell, a temperature-
1
3. Bel’skii, V.E., Novikova, L.S., Kudryavtseva, L.A.,
and Ivanov, B.E., Zh. Obshch. Khim., 1978, vol. 48,
no. 7, p. 1512.
14. Menger, F.M., Gan, L.H., Johnson, E., and Durst, D.H.,
J. Am. Chem. Soc., 1987, vol. 109, no. 9, p. 2800.
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INVERSE MICELLAR CATALYSIS OF PHOSPHORYLATION
1609
1
1
5. Arcelli, A. and Concilio, C., J. Chem. Soc., Perkin
Trans. 2, 1983, no. 9, p. 1327.
17. Gur’yanova, E.N., Gol’dshtein, I.P., and Romm, I.P.,
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Bond), Moscow: Khimiya, 1973.
6. Gordon, A.J. and Ford, R.A., The Chemist’s Com-
panion. A Handbook of Practical Data, Techniques,
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18. Nigmatullin, R.Sh., Vyaselev, M.R., and Shatu-
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