Effect of structural preorganization on the reactivity of carbazoylmethyl derivatives of pyrogallol and calix[4]pyrogallol

Article abstract of DOI:10.1007/s11172-007-0381-9

The aggregation behavior of carbazoylmethyl derivatives of pyrogallol and calix[4]pyrogallol was studied by conductometry and dynamic light scattering in water-DMF media. The formation of mixed nanoaggregates in the presence of cationic surfactants was re

Full text of DOI:10.1007/s11172-007-0381-9

Russian Chemical Bulletin, International Edition, Vol. 56, No. 12, pp. 2394—2399, December, 2007
2394
Effect of structural preorganization on the reactivity of carbazoylmethyl
derivatives of pyrogallol and calix[4]pyrogallol

T. N. Pashirova, M. V. Leonova, S. N. Podyachev, S. N. Sudakova, L. Ya. Zakharova,
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 (843) 273 2253. Eꢀmail: spodyachev@iopc.knc.ru
The aggregation behavior of carbazoylmethyl derivatives of pyrogallol and calix[4]pyrogallol
was studied by conductometry and dynamic light scattering in water—DMF media. The forꢀ
mation of mixed nanoaggregates in the presence of cationic surfactants was revealed. The effect
of structural preorganization of these compounds on their reactivity in the acylation by
4ꢀnitrophenylacetate and the catalytic activity in the hydrolysis of phosphorus acid esters was
studied.
Key words: micelles, critical micelle concentration, kinetics, hydrolysis, acylation,
hydrazides, cationic surfactants, calix[4]pyrogallol, organophosphorus compounds.
Calixarenes are typical objects of supramolecular
effect of the functional groups on the catalytic properties
was observed26 for the supramolecular models of enzymes.
In the present work, we studied the acylation
of the NH2 groups of the hydrazine fragments of
calix[4]pyrogallol 1 and its structural analog 2 with
4ꢀnitrophenylacetate (pꢀnitrophenylacetate, PNPA) as the
acyl group donor. This was done in order to reveal the
chemistry capable of noncovalent binding of organic comꢀ
pounds.1—5 The application of calixarenes is known6—9 in
analytical chemistry, ecology, lithography, in the creꢀ
ation of film materials, catalysts, etc. We have previously
obtained10—13 data on the selfꢀorganization of amphiphilic
calixarenes and showed9,14—16 a substantial effect of agꢀ
gregation on their catalytic activity in the reactions with
phosphorus and carboxylic acid esters.
We have recently17—19 reported the synthesis and charꢀ
acterization of new calix[4]arenes functionalized by the
carbazoylmethyl groups. Acyl hydrazides find use as drugs,
complexones, and photoꢀ and thermochromic materiꢀ
als.20—22 At the same time, they are key reactants in the
syntheses of many organic compounds.23—25 The syntheꢀ
sized hydrazide derivatives of calix[4]resorcinol and
calix[4]pyrogallol exist in the boat conformation. For all
calix[4]arenes under study, including their model comꢀ
pounds,17,19 the transꢀstructure of the amide moiety of
the hydrazide group was found.
Solubility of calix[4]phenols with acetylhydrazide
groups in organic solvents, in particular, in chloroform,
made it possible to study their extraction properties toꢀ
ward a series of transition metal ions.18 This study showed
that the high extraction ability of these compounds comꢀ
pared to that of their structural unit, namely, 4ꢀtertꢀbuꢀ
tylphenoxyacetylhydrazide, is caused by the preorganizaꢀ
tion of the hydrazide groups on the calixarene platform
resulting in the positive cooperative effect in binding of
metal ions. An important influence of the cooperative
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2312—2317, December, 2007.
1066ꢀ5285/07/5612ꢀ2394 © 2007 Springer Science+Business Media, Inc.

Preorganization and reactivity of hydrazides
Russ.Chem.Bull., Int.Ed., Vol. 56, No. 12, December, 2007 2395
order reaction in the solvent bulk and in the micellar phase, s–1
;
role of structural preorganization of the hydrazide groups
and the effect of aggregation on the reactivity and catalytꢀ
ic activity. The hydrolysis of P,Pꢀbis(chloromethyl)ꢀOꢀ
(4ꢀnitrophenyl)phosphinate (BCNPP) catalyzed by comꢀ
pound 1 was also studied in aqueous DMF (30 vol.%) in a
wide concentration range.
Ks is the binding constant of the substrate with the micelle,
L mol–1; CSurf is the surfactant concentration, mol L–1; CMC is
the critical micelle concentration, mol L–1
.
Results and Discussion
Calix[4]pyrogallol 1 containing the hydrophilic acetylꢀ
hydrazide groups and hydrophobic aryl fragments is inꢀ
soluble in lowly polar solvents but is soluble in water.17 Its
structural analog 2 possess similar properties. Therefore,
these compounds are of interest in studying the influence
of aggregation and preorganization of the functional
groups on their reactivity in aqueous and aqueousꢀorganꢀ
ic media.
The aggregation of the derivatives of calix[4]pyrogallol
1 and pyrogallol 2 was studied by conductometry and
dynamic light scattering. The curve of the dependence of
the electrical conductivity on the concentration of comꢀ
pound 1 (Fig. 1) contains two inflections corresponding
to the onset of aggregation (CMC1 = 1.2•10–5 mol L–1
)
and structural rearrangement in the system (CMC2
=
1.5•10–3 mol L–1). According to the light scattering data,
the radius of the aggregates of calix[4]pyrogallol 1 at a
concentration of 2.5•10–3 mol L–1 is 137 nm, whereas
Experimental
the radius is 141 nm at a concentration of 1•10–3 mol L–1
,
Commercial PNPA (Fluka) was used; BCNPP was syntheꢀ
sized according to a known procedure.27 The reactions of ethyl
bromoacetate with pyrogallol and calix[4]pyrogallol afforded
esters of the corresponding areneꢀ1,2,3ꢀtriylꢀtris(hydroxyacetic
acids), which were transformed by the subsequent treatment
with excess hydrazine hydrate into hydrazides 1 and 2 according
to a procedure described by us earlier.17
All measurements were carried out in a water—DMF
(30 vol.%) medium at 30 °C. Electrical conductivity was meaꢀ
sured on a CDMꢀ2d conductometer (Denmark). The electrical
conductivity of bidistilled water used for the preparation of soluꢀ
tions of the reactants was taken as the zero value. The effective
radii of the aggregates were determined on a Photocor Complex
dynamic light scattering instrument and calculated from the
diffusion coefficients by the Stokes—Einstein equation for spherꢀ
ical particles of the same size with allowance for the viscosity of
the solutions under study. For each system the hydrodynamic
radius was determined as the arithmetical average of the results
of ten measurements.
i.e., in the region from CMC1 to CMC2. Evidently, the
structure of the aggregates is formed due to intermolecuꢀ
lar hydrogen bonding (IMHB) of the —C=O...H—N—
and —N—H...N— types, which were observed in
calix[4]arene hydrazides and their monomeric analogs in
the solid state and in solutions according to Xꢀray diffracꢀ
tion and IR and NMR spectroscopic data.17,19,29,30 Strucꢀ
χ/µS cm–1
9
a
The kinetics of the acylation and hydrolysis processes was
studied by spectrophotometry on a Specord UV—Vis instrument
at the initial substrate concentrations 5•10–5—1•10–4 mol L–1
and different pH values at 30 °C in a water—DMF (30 vol.%)
medium. The reaction course was monitored by the change in
the absorbance of solutions at a wavelength of 400 nm (formaꢀ
tion of the 4ꢀnitrophenolate anion). The conversion was higher
than 90%. The apparent rate constants of the firstꢀorder reacꢀ
tion (kapp, s–1) were calculated by the regression method using
the equation
8
2
4
C1•105/mol L–1
χ/µS cm–1
60
b
ln(D∞ – Dt) = –0.434kappt + const,
(1)
40
20
where D∞ and Dt are the absorbances upon the cessation of the
reaction and at the time t.
The kinetic dependences were analyzed by the equation of
the pseudoꢀphase model of micellar catalysis28a
kapp = [kw + kmKs(CSurf – CMC)]/[1 +
10
20
+ Ks(CSurf – CMC)],
(2)
C1•104/mol L–1
Fig. 1. Plots of the electrical conductivity vs concentration of
compound 1 in the region of CMC1 (a) and CMC2 (b).
where kapp is the apparent rate constant of the pseudoꢀfirst order
reaction, s–1; kw and km are the rate constants of the pseudoꢀfirst

2396
Russ.Chem.Bull., Int.Ed., Vol. 56, No. 12, December, 2007
Pashirova et al.
kapp•103/s–1
tural arrangements in the system can be caused by a change
in the shape or sizes of the associates. The carbazoylmeꢀ
thyl derivative of pyrogallol 2 is also aggregated in a waꢀ
ter—DMF medium (CMC = 3•10–3 mol L–1).
12
8
It is known31—33 that unsubstituted calix[4]pyrogallols
in both the solid state and solutions form stable hexamerꢀ
ic aggregates. This process can additionally involve water
molecules or metal cations. The nanospheroidal strucꢀ
tures obtained from these compounds are stable even in
polar waterꢀcontaining media.31 However, the size of these
aggregates (diameter less than ∼19 nm)32,33 is substantialꢀ
ly smaller than the size of the structures in our case. The
substitution of the hydrogen atoms of the hydroxy groups
for the carbazoylmethyl moieties favors, most likely, the
formation of a more complex and saturated network of
hydrogen bonds. This can be a main reason for the enꢀ
hanced stability of the aggregates in our case and for their
considerable sizes.
1
4
2
8
9
10 pH
Fig. 2. Dependence of kapp of the acylation of compounds 1 and
2 on pH (C1 = 1.5•10–3 mol L–1, C2 = 6•10–3 mol L–1).
The kinetics of the acylation of derivatives 1 and 2 by
PNPA in a water—DMF medium was studied (Scheme 1).
kapp•103/s–1
7
6
5
4
Scheme 1
1.0
1.5
2.0
C1•103/mol L–1
Fig. 3. Dependence of kapp of the acylation on the concentration
of calix[4]pyrogallol 1 (pH = 9.5).
The dependence of the apparent rate constant (kapp
,
substrate (aggregate—substrate complex) due to noncoꢀ
valent interactions similarly to the formation of the enꢀ
zyme—substrate and micelle—substrate complexes.28b,34
The data shown in Fig. 3 were processed using Eq. (2) of
the pseudoꢀphase model of micellar catalysis. The paramꢀ
eters obtained are given in Table 1. Rather high binding
constant of PNPA (Ks = 1300 L mol–1) with the forming
aggregates of calix[4]pyrogallol 1 suggests that the factor
s–1) of the acylation of compounds 1 and 2 on the pH
value is presented in Fig. 2. These data show that the
reactivity of the macrocycle is much higher than that of
its monomeric analog. The plot of the apparent rate conꢀ
stant vs concentration of 1 is nonlinear and reaches a
plateau (Fig. 3). This confirms the formation of associates
of compound 1 capable of preꢀreaction binding of the
Table 1. Parameters of the acylation of calix[4]pyrogallol 1 by PNPA in the absence and in the presence of
CSurf (pH = 9.5)
System
CMC/mol L–1
km•102/s–1
Ks/L mol–1
km/k0
1—H2O—DMF
CSurf1—1b—H2O—DMF
CSurf2—1b—H2O—DMF
5.8•10–4
3.6•10–5
1.2•10–4
1.1
3.1
4.4
1.3•103
9.5•102
1.3•103
22a
4c
6c
a Acceleration of the rate constant of the acylation of compound 2 (6•10–3 mol L–1) at pH = 9.5
(k0 = 5•10–4 s–1).
b C1 = 1.5•10–3 mol L–1
.
c Acceleration over the rate constant of the acylation of compound 2 (6•10–3 mol L–1) in the absence of
CSurf at pH = 9.5 (k0 = 7.5•10–3 s–1).

Preorganization and reactivity of hydrazides
Russ.Chem.Bull., Int.Ed., Vol. 56, No. 12, December, 2007 2397
Table 2. The CMC values (mol L–1) for CSurf in the absence (I) and presence (II) of calix[4]pyrogallol 1
(C1 = 1.5•10–3 mol L–1
)
Parameter
CSurf1
CSurf2
CSurf3
I
II
I
II
I
II
CMC1
CMC2
5•10–4
6.5•10–3
5•10–5
2•10–4
6•10–4
7•10–3
3•10–5
1.5•10–4
2•10–5
1.2•10–4
1•10–5
—
of reactant concentrating makes the main contribution to
the process under study.
cationic surfactants in the absence and presence of 1 are
presented in Table 2. Figure 4 shows as an example the
dependence of the electrical conductivity on the CSurf1
concentration in the presence of compound 1. The deꢀ
crease in the CMC upon the addition of macrocycle 1 to
the system, according to published data,39 favors the forꢀ
mation of combined aggregates due to hydrogen bonds of
the hydrazide fragments with the OH groups of the moleꢀ
cules or micelles of CSurf. It can be assumed that these
bonds are stronger than the IMHB between the hydrazide
groups of the molecules in compound 1. This can decomꢀ
pose an aggregate of calix[4]pyrogallol, after which its
molecules interact with the CSurf micelles to form comꢀ
bined structures.
The size of the aggregates in a calix[4]pyrogallol 1
(1•10–3 mol L–1)—CSurf2 (4•10–4 mol L–1)—water—
DMF system was determined by dynamic light scattering
and showed a decrease in the radius of the aggregates of
calix[4]arene 1 in the presence of CSurf2 (from 141 to
125 nm). It is known9,40 that for the cationic surfactants
the radius of the micelles in water and in a water—DMF
(30 vol.%) medium is ∼2.5—3 nm.
The reactivity of the monomeric structural analog 2 in
the acylation at the concentration exceeding by 4 times
the concentration of macrocycle 1 (see Table 1) is by
∼20 times lower. This is distinctly seen from the data in
Fig. 2 exhibiting the plots of kapp vs pH for the reactions of
compounds 1 and 2 with PNPA.
At present, binary mixtures of amphiphilic comꢀ
pounds forming combined nanoaggregates with specific,
including catalytic, properties are of great interest for
controlling the rates of chemical processes.35—38
Calix[4]pyrogallol 1 was acylated in micellar solutions of
cationic surfactants (CSurf) containing the hydroxyalkyl
groups: cetyldimethyl(2ꢀhydroxypropyl)ammonium
(CSurf1) and cetylmethyldi(2ꢀhydroxyethyl)ammonium
(CSurf2) bromides. In this case, the systems based on
calix[4]pyrogallol 1 and CSurf consist of the components
capable of selfꢀassociating. In addition, compound 1 conꢀ
tains the carbazoylmethyl groups that can be involved in
chemical processes.
Calix[4]pyrogallol 1 was found to affect the CMC of
the detergents decreasing them. The CMC values of the
The plots of kapp of the acylation of 1 with PNPA vs
CSurf concentration are presented in Fig. 5. It is seen that
the rate of the process in the micellar systems increases by
4—6 times. The results of quantitative processing of the
nonlinear dependences Kapp = f(СCSurf) by Eq. (2) of the
pseudoꢀphase model are given in Table 1. The binding
constants of the substrate (PNPA) in CSurf2 solutions
χ/µS cm–1
70
kapp•102/s–1
2
65
60
55
3
1
2
1
CCSurf•103/mol L–1
10
20
CCSurf •104/mol L–1
1
1
2
Fig. 4. Dependence of the electrical conductivity on the CSurf1
Fig. 5. Plots of kapp of the acylation of calix[4]pyrogallol 1 vs
concentration of CSurf1 (1) and CSurf2 (2); water—DMF
(30 vol.%), pH = 9.5.
concentration in the presence of calix[4]pyrogallol 1 (C1
=
1.5•10–3 mol L–1).

2398
Russ.Chem.Bull., Int.Ed., Vol. 56, No. 12, December, 2007
Pashirova et al.
Table 3. Parameters of the hydrolysis of BCNPP
System
рН
k0a/s–1
km•10–2
/s–1
Ks
/L mol
CMC
/L mol
km/k0
–1
–1
1—H O—DMF
9.5
9.0
1.58•10–2
5•10–3
9.6
4.1
1260
2400
2.6•10–3
1.6•10–5
6
8
2
b
CSurf —1 —H O—DMF
3
2
a Rate constant of the hydrolysis of BCNPP in the absence of compound 1 and surfactant.
b С1 = 3.5•10–3 mol L–1
.
(1300 L mol–1) are higher than Ks in the system based on
CSurf1 (950 L mol–1), suggesting the direct participation
of the hydroxyalkyl groups of CSurf in the binding.
The catalytic activity of calix[4]pyrogallol 1 was studied
using the hydrolysis of BCNPP as an example (Scheme 2).
The formation of bis(chloromethyl)phosphinic acid
(δ = 27.6) in this reaction was confirmed by the 31P NMR
method. The chemical shift of BCNPP in a water—DMF
medium is 32.2 ppm.
The plots of the apparent rate constant of the hydrolyꢀ
sis of BCNPP vs concentration of calix[4]pyrogallol 1 and
vs pH are shown in Figs 6 and 7, respectively. The results
of quantitative processing of the data in Fig. 6 using Eq.
(2) are given in Table 3. The hydrolysis in the presence of
compound 1 is accelerated by 6 times compared to the
alkaline hydrolysis of BCNPP under the same conditions.
The acceleration of the hydrolysis in the presence of strucꢀ
tural analog 2 in a concentration of 1.6•10–2 mol L–1
Scheme 2
(ClCH2)2P(O)OC6H4NO2ꢀ4 + H2O →
→ (ClCH2)2P(O)OH + HOC6H4NO2ꢀ4
(pH = 9.5) is by ~2 times lower (kapp = 1.8•10–2 s–1
)
kapp•102/s–1
than that in the presence of calix[4]pyrogallol 1
(kapp = 4•10–2 s–1) in the concentration ~5ꢀfold lower
(3•10–3 mol L–1).
6
4
2
The effect of a geminal surfactant, viz., hexylideneꢀ
1,6ꢀbis(dimethylcetylammonium) dibromide (CSurf3), on
the hydrolysis of BCNPP catalyzed by compound 1
(Fig. 8) and the influence of the latter on the CMC1 of
this surfactant (see Table 2) were revealed. In a CSurf—
macrocycle 1 mixed system an increase in the binding
constant of the substrate compared to the system in the
absence of a detergent is observed. However, the comꢀ
bined aggregates exert a catalytic effect that differs insigꢀ
nificantly from the catalytic activity of the aggregates of
calix[4]pyrogallol 1 itself (see Table 3).
1
2
3
C1•103/mol L–1
Fig. 6. Dependence of kapp of the hydrolysis of BCNPP on the
concentration of calix[4]pyrogallol 1 (pH = 9.0).
Thus, aggregate formation due to intermolecular
hydrogen bonds between the carbazoyl groups of calix[4]ꢀ
kapp•102/s–1
kapp•102/s–1
4
2.0
2
1.5
2
4
CCSurf •104/mol L–1
3
8
9
pH
Fig. 8. Dependence of kapp of the hydrolysis of BCNPP on the
concentration of CSurf3 in the presence of calix[4]pyrogallol 1
(C1 = 3.5•10–3 mol L–1, pH = 9.0).
Fig. 7. Dependence of kapp of the hydrolysis of BCNPP on pH in
the presence of calix[4]pyrogallol 1 (C1 = 3.0•10–3 mol L–1).

Preorganization and reactivity of hydrazides
Russ.Chem.Bull., Int.Ed., Vol. 56, No. 12, December, 2007 2399
Sudakova, W. D. Habicher, and А. I. Konovalov, Spectroꢀ
chim. Acta, Part A: Molecular and Biomolecular Spectroscopy,
2007, 66, 250.
pyrogallol 1 molecules increases its reactivity in the acyꢀ
lation and the catalytic activity in the hydrolysis of phosꢀ
phorus acid esters compared to the reactivity of its strucꢀ
tural unit 2. The formation of the combined aggregates of
calix[4]pyrogallol 1 with the cationic surfactant enhances
its ability to acylation and catalytic effect.
20. E. Schmidt, Hydrazine and its Derivatives: Preparation, Propꢀ
erties, Applications, 2nd ed., Wiley, New York, 2001.
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khimicheskie svoistva i stroenie [Transition Metal Complexes
with Hydrazones: Physicochemical Properties and Structure],
Nauka, Moscow, 1990, 109 pp. (in Russian).
22. R. I. Machkhoshvili and R. N. Shchelokov, Koord. Khim.,
2000, 26, 723 [Russ. J. Coord. Chem., 2000, 26, 677 (Engl.
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23. P. V. Bernhardt, P. Chin, and D. R. Richardson, J. Biol.
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This work was financially supported by the Russian
Foundation for Basic Research (Project No. 07ꢀ03ꢀ
00325ꢀa).
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