Synthesis, spectral properties, and antimicrobial activity of 2-arilamino-2,4,4,6,6-pentachloro-1,3,5,2λ5, 4λ5,6λ5-triazatriphosphines and poly[bis(4-fluorophenylamino)phosphazene]

Article abstract of DOI:10.1134/S1070363207120079

2-(4-Chloro and 4-fluorophenylamino)-2,4,4,6,6-pentachloro-1,3,5, 2λ⁵,4λ⁵,6λ⁵- triazatriphosphinines and poly[bis(4-fluorophenylamino)phosphazene] were synthesized by reactions of 4-fluoroaniline and 4-chloroaniline with 2

Full text of DOI:10.1134/S1070363207120079

ISSN 1070-3632, Russian Journal of General Chemistry, 2007, Vol. 77, No. 12, pp. 2117 2122.
Pleiades Publishing, Ltd., 2007.
Original Russian Text M. Yildiz, S. Yilmaz, B. Dolger, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 12, pp. 1972 1977.
Synthesis, Spectral Properties, and Antimicrobial Activity
5
5
5
of 2-Arilamino-2,4,4,6,6-Pentachloro-1,3,5,2 ,4 ,6 -
Triazatriphosphines
and Poly[Bis(4-Fluorophenylamino)Phosphazene]
M. Yildiza, S. Yilmaza, and B. Dolgerb
a Department of Chemistry, Faculty of Arts and Sciences,
Çanakkale Onsekiz Mart University, 17100 Çanakkale, Turkey
fax: +(90286)218-05-33
e-mail: myildiz@comu.edu.tr
b Department of Biology, Faculty of Arts and Sciences,
Çanakkale Onsekiz Mart University, 17100 Çanakkale, Turkey
Received November 8, 2006
Abstract 2-(4-Chloro and 4-fluorophenylamino)-2,4,4,6,6-pentachloro-1,3,5,2 5,4 5,6 5-triazatriphos-
phinines and poly[bis(4-fluorophenylamino)phosphazene] were synthesized by reactions of 4-fluoroaniline
and 4-chloroaniline with 2,2,4,4,6,6-hexachloro-1,3,5,2 5,4 5,6 5-triazatriphosphinine and poly(dichloro-
phosphazene), respectively, in tetrahydrofuran under argon at 20 C, followed by heating under reflux. The
products were isolated by column chromatography and were characterized by FTIR, NMR (1H, 13C, 31P),
and mass spectra, termogravimetry, and high-performance liquid chromatography. Antimicrobial activity of
the monomeric compounds and polymer against 9 bacteria and 5 yeast cultures was evaluated by the disk
diffusion method in dimethyl sulfoxide relative to a number of commercial antibiotics and antifungal agents.
Aminophosphazene derivatives exhibited a broad spectrum of activity against both Gram-positive and Gram-
negative bacterial with a magnitude comparable to reference antimicrobial agents. The polymeric product
turned out to be more potent than the monomeric compounds.
DOI: 10.1134/S1070363207120079
During the past decade, reactions of hexachloro-
cyclotriphosphazene N3P3Cl6 with primary and sec-
ondary amines, diamines, polyamines, hydroxylamine
[1 6], phenols [7 9], alcohols, and oligo(ethylene
glycols) [10] have been studied under different condi-
tions with the goal of obtaining macrocyclic cyclo-
phosphazene ethers [11]. Polyphosphazenes constitute
a large class of inorganic polymers whose backbone
incorporates alternating phosphorus and nitrogen
atoms. Versatile reactivity of the precursor, poly(di-
chlorophosphazene) (NPCl2)x, makes it possible to
introduce various side organic groups into the poly-
meric chain via nucleophilic replacement of chlorine
on the phosphorus [12 14]. As a result, polymeric
products possessing practically important properties
could be obtained, e.g., polymeric electrolytes
[14, 15], compounds with unusual thermal propeties
[16, 17], biocompatible substances [18], and com-
pounds having interesting optical properties [19, 20];
some of these derivatives attract interest from the
commercial viewpoint. Therefore, phosphazenes have
received increasing attention. On the other hand,
polyanilines have been studied extensively for
numerous potential applications due to their high
conductivity, electroactivity, and other unique
properties [21 23].
Here we report on the synthesis of 2,4,4,6,6-penta-
5
5
5
chloro-2-(4-fluorophenylamino)-1,3,5,2 ,4 ,6 -tr-
iazatriphosphinine (I), 2,4,4,6,6-pentachloro-2-(4-
chlorophenylamino)-1,3,5,2 5,4 5,6 5-triazatriphos-
phinine (II), and poly[bis(4-fluorophenylamino)phos-
phazene] (IV) and on their antimicrobial activity in
vitro. The structure of the monomeric and polymeric
products was determined by elemental analysis, FTIR
spectroscopy, 1H, 13C, and 31P NMR, thermogra-
vimetric analysis, and high-performance liquid
chromatography (HPLC).
The IR spectra of compounds I, II, and IV con-
tained absorption bands belonging to vibrations of
N H bonds at 3180, 3161 and 3366 (m), C=C bonds
at 1509, 1495, and 1511 (s), C N bonds at 1377, 1376,
and 1382 (m), and P=N bonds at 1196, 1189, and
1
1211 cm (s), respectively (Fig. 1). Unlike polymeric
2117

2118
YILDIZ et al.
H
Cl
N
P
N
Cl
N
P
Cl
N
P
4-XC6H4NH2 (2 equiv)
THF, 20 C
P
P
N
X
4-XC6H4NH3+ Cl
Cl
Cl
Cl
Cl
Cl
Cl
P
Cl
Cl
N
N
I, II
250 C
C6H4F-4
4-FC6H4NH2 (excess)
THF, 20 C
NH
P=N
NH
Cl
4-XC6H4NH3+ Cl
P=N
Cl
n
n
4-FC6H4
III
IV
I, X = F; II, X = Cl.
phosphazene IV, compounds I and II showed (P Cl)
bands at 592, 523 and 598, 526 cm , respectively.
sponding band in the spectra of octachlorocyclotetra-
1
1
phosphazene (1310 cm ), decachlorocyclopentaphos-
1
The position of the P=N absorption band in the IR
spectrum of initial hexachlorocyclotriphosphazene
phazene (1355 cm ), dodecachlorocyclohexaphos-
1
phazene (1325 cm ), tetradecachlorocycloheptaphos-
1
1
(1215 cm ) is similar to the position of the corre-
phazene (1310 cm ), and higher cyclic homologs and
(b)
(a)
1495.03
526.04
1509.13
592.11
1189.11
598.78
1196.26
523.67
1
1
, cm
, cm
(c)
1511.18
1211.32
4000
3200 2400 1800 1400 1000 600
, cm
1
Fig. 1. IR spectra of compounds (a) I, (b) II, and (c) IV.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 77 No. 12 2007

SYNTHESIS, SPECTRAL PROPERTIES, AND ANTIMICROBIAL ACTIVITY
2119
1
polymer (1305 cm ), as well as of acyclic mono-
TG 136 C
675 C
100
90
80
70
60
50
40
30
20
10
0
1
phosphazenes (1160 1230 cm ) [24]. The P=N
stretching vibration frequencey in the IR spectrum of
monomer I is lower by 15 cm than that observed for
polymer IV. The presence of chlorine atoms increases
the intensity of the (P=N) band in the spectrum of
poly(dichlorophosphazene) (III) as compared to poly-
[bis(4-fluorophenylamino)phosphazene] (IV) contain-
ing electron-withdrawing 4-fluorophenylamino groups.
50%
438 C
5
4
1
510 C
3
2
1
248 C
DTA
34%
500
0
1
300 C
The H and 13C NMR spectra of the obtained com-
1
pounds are given in Experimental. The NH proton
signal appears as a singlet at 5.52 ppm, doublet at
5.59 ppm (2JPH = 9.0 Hz), or doublet at 5.40 ppm
100
300
700
900
1100
Temperature, C
(2JPH = 20 Hz) in the H NMR spectra of I, II, and
1
Fig. 2. Data of thermogravimetric and differential
thermal analysis of polymer IV.
IV, respectively. Aromatic protons resonated at
,
ppm: 6.93, 7.09 m (I); 7.18, 7.38 d.d (II); 7.07,
7.19 m (IV). The 13C NMR spectra of I and IV re-
corded with decoupling from protons contained six
signals, whereas compound II displayed four signals.
This means that cyclotriphosphazene IImolecules) in
solution have symmetrical structure and that mole-
cules I and IV are not symmetric. The 13C 31P coup-
ling constants through two, three, four, and five bonds
in IV are much greater than the corresponding con-
stants for compound I. The C1 (ipso) and C3 (meta)
aromatic nuclei in molecule I interact with the phos-
phorus nucleus, while fluorine-containing polyphos-
phazene lacks such interactions.
The 31P NMR spectra of I, II, IV may be inter-
preted as AB2, AB2, and An spin systems, respectively.
According to the 31P NMR data, no higher cyclophos-
phazene homologs are formed in the polymerization
of hexachlorocyclotriphosphazene: the spectrum of
polymer IV contained the only phosphorus signal at
oxidation of the polymer. The corresponding weight
loss amounts to 34% in the TG curve and represents
liberation of CO2, H2O, and NH3. The product formed
after decomposition in the range 400 700 C is stable
up to 1200 C. Presumably, thermal degradation of
polymer IV is a complicated process involving both
transformations of particular groups and oxidation.
The results of testing compounds I, II, and IV for
antibacterial activity are summarized in the table; for
comparison, the corresponding data for reference anti-
biotics are given. It is seen that compounds I, II, and
IV are active against both Gram-positive and Gram-
negative bacteria and yeast cultures, although the
activity against Gram-positive bacteria is usually
higher than against Gram-negative bacteria [25].
Polymer IV showed the strongest effect against all
tested bacteria. Compounds I, II, and IV turned out
to be more active with respect to Staphylococcus
aureus than reference antibiotics except for Ofloxacin
and Tetracyclin. Compounds I and IV were more
active than Cefotaxime against acid-fast Mycobacte-
rium smegmatis but less active than reference anti-
biotics against Micrococcus luteus and Proteus
vulgaris (except for Penicillin in the latter case). A
strong effect was also observed toward Bacillus
cereus and Escherichia coli. Compounds I, II, and IV
also showed more or less pronounced activity against
other bacteria.
6.31 ppm.
P
Study of the molecular weight distribution in
polymeric products III and IV gave the following
values: number-average molecular weight Mn 766864
1
and 659959 g mol , weight-average molecular weight
1
Mw 770105 and 688215 g mol , and polydispersity
index (PDI) 1.004 and 1.042, respectively.
The thermal stability of polyphosphazene IV was
studied under atmospheric conditions in the tempera-
ture range from 20 to 1200 C. Figure 2 shows the TG
and DTA curves for polymer IV. It is seen that de-
composition starts at 136 C. Increase in the tempera-
ture from 136 to 381 C is accompanied by 50%
weight loss, and it reaches 84% at 845 C. The DTA
curve reveals two endothermic reactions at 300 and
510 C. Taking into account 50% weight loss, the
observed peaks were attributed to structural rearrange-
ments. Strong exothermic effects in the regions
400 450 and 650 700 C are likely to result from
Polymer IV was more efficient than commercial
antifungal agents (such as Nystatin, Ketoconazole, and
Clotrimazole) in tests with the yeast cultures Candida
albicans and Kluyveromyces fragilis. Compounds I,
II, and IV showed different activities against other
microorganisms. These differences may be rational-
ized in terms of different structures of cell membranes:
cell membrane of Gram-positive bacteria consists of a
single layer, Gram-negative bacteria have multilayered
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 77 No. 12 2007

2120
YILDIZ et al.
Antibacterial activity of compounds I, II, and IV and some commercial antibiotics a
Inhibition zone diameter, mm
Microorganism
I
II
IV
P10 AM20 CTX30 VA30 OFX5 TE30 NY100 KET20 CLT10
Escherichia coli
Staphylococcus
aureus
15
16
14
16
19
22
18
13
12
16
10
12
22
13
30
24
28
26
Klebsiella
13
14
17
18
18
8
14
10
13
54
22
10
28
44
30
34
pneumoniae
Pseudomonas
aeruginosa
11
Proteus vulgaris
Bacillus cereus
Mycobacterium
smegmatis
11
17
12
14
13
13
20
16
10
14
15
16
12
21
18
14
11
20
18
20
28
30
32
26
25
24
Listeria mono-
cytogenes
Micrococcus
luteus
Candida albicans
Kluyveromyces
fragilis
17
15
14
14
18
17
10
36
12
32
16
32
26
34
30
28
28
22
18
14
22
22
20
18
21
16
15
18
Rhodotorula
rubra
15
20
18
22
16
H. guilliermondii
Debaryomyces
hansenii
14
14
10
12
19
16
21
16
24
14
22
18
a
P10 is Penicillin G, 10 units; AM20 is Ampicillin, 10 g; CTX30 is Cefatoxime, 30 g; V30 is Vancomycin, 30 g; OFX5 is
Ofloxacin, 5 g; TE30 is Tetracyclin, 30 g; N100 is Nystatin, 100 g; KET20 is Ketoconazole, 20 g; and CLT10 is Clotrimazole,
10 g.
cell membranes, while yeast cell wall has even more
complex structure [26].
molecular sieves. 4-Fluoroaniline and 4-chloroaniline
(Merck) were used without additional purification.
Column chromatography was performed on silica gel
(70 230 mesh, 60 ; Aldrich); Kieselgel 60 F 254
plates were used for thin-layer chromatography. All
operations were performed under argon using standard
Thus, the results of biological studies show that
phosphazene derivatives are capable of generating
novel metabolites displaying high affinity for most
receptors. The strong anticandidal effect of these
compounds makes them promising from the viewpoint
of developing new anticandidal agents with a broad
spectrum of activity. Compounds I, II, and IV may
be selected for further pharmacological tests as po-
tential drugs against many infectious diseases.
1
Schlenk glassware. The H, 13C, and 31P NMR spectra
were recorded on a Bruker DPX spectrometer at 400,
1
101.6, and 161.99 MHz, respectively. The H and 13C
chemical shifts were measured relative to tetramethyl-
silane as internal reference; the 31P chemical shifts
were determined relative to 85% H3PO4 (external).
The IR spectra were recorded on a Perkin Elmer BX
II instrument from samples prepared as KBr pellets.
The elemental compositions were determined on a
LECO CHNS-932 C,H,N analyzer. The melting points
were measured on an Electrothermal IA 9100 ap-
paratus in capillaries. Thermogravimetric analysis was
performed on an NETZSCH Simulton Thermal
Analyzer STA 409 EP instrument in the temperature
EXPERIMENTAL
Commercial hexachlorocyclotriphosphazene (2,2,4,
4,6,6-hexachloro-1,3,5,2 5,4 5,6 5-triazatriphosphi-
nine, Aldrich) was recrystallized from hexane and
additionally purified by fractional vacuum sublimation
at 55 C just before use. Benzene, tetrahydrofuran, and
hexane (Merck) were distilled over metallic sodium
in the presence of benzophenone and were stored over
1
range from 20 to 1200 C (rate 10 deg min ) in air.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 77 No. 12 2007

SYNTHESIS, SPECTRAL PROPERTIES, AND ANTIMICROBIAL ACTIVITY
2121
The number-average (Mn) and weight-average (Mw)
molecular weights and polydispersity indices (PDI)
were determined by size-exclusion chromatography
(SEC) on a Shimadzu instrument equipped with a
refractive index detector (25 C) and a 3.3 300-mm
column packed with SGX (grain size 100 , pore
diameter 7 nm); dimethylformamide was used as
m/z for 35Cl (Irel, %): 441 (35) [M + 2H], 439 (55)
[M]+, 437 (100) [M 2H]+, 402 (23) [M HCl]+, 312
(53) [M NHC6H4Cl]+. Found: C 16.30; H 1.13; N
12.76. C6H5Cl6N4P3. Calculated, %: C 16.40; H 1.14;
N 12.77.
Poly(dichlorophosphazene) (III) was synthesized
and purified according to the procedures described in
1
eluent (flow rate 0.4 ml min ), and polystyrene was
used as standard.
1
[12, 27]. IR spectrum (KBr), , cm : 1255 s (P=N);
1
766 s, 578 s (P Cl). Mn = 766864 g mol ; Mw =
1
2,4,4,6,6-Pentachloro-2-(4-fluorophenylamino)-
770105 g mol ; PDI = 1.004.
5
5
5
1,3,5,2 ,4 ,6 -triazatriphosphinine (I). A solu-
tion of 3.19 g of 4-fluoroaniline in 50 ml of anhydrous
THF was added dropwise over a period of 1 h to a
solution of 5.0 g of hexachlorocyclotriphosphazene in
100 ml of anhydrous THF under stirring at 20 C in
an argon atmosphere. The mixture was allowed to
warm up to room temperature and was then heated
under reflux for 4 h with protection from atmospheric
moisture. The precipitate of 4-fluoroaniline hydro-
chloride was filtered off, the filtrate was evaporated
on a rotary evaporator, and the residue was subjected
to column chromatography on silica gel (120 g) using
chloroform as eluent. The product was additionally
purified by recrystallization from methylene chloride
n-hexane (3:1). Yield 3.76 g (62%), white crystals,
Poly[bis(4-fluorophenylamino)phosphazene]
(IV). A solution of 19.13 g of 4-fluoroaniline in 50 ml
of anhydrous THF was added dropwise over a period
of 1 h to a solution of 5.0 g of poly(dichlorophos-
phazene) (III) in 150 ml of anhydrous THF under
stirring at 20 C in an argon atmosphere. The mixture
was allowed to warm up to room temperature and was
then heated under reflux for 48 h with protection from
atmospheric moisture. The precipitate of 4-fluoro-
aniline hydrochloroide was filtered off, the filtrate was
evaporated on a rotary evaporator, the residue was
treated with water, and the product was extracted into
chloroform. Yield 9.98 g (87%), brown solid, mp
1
>300 C (decomp.). IR spectrum (KBr), , cm :
3366 m (N H), 1511 s (C=C), 1370 m (C N), 1211 s
1
mp 54 C. IR spectrum (KBr), , cm : 3180 m (N H);
(P=N). 31P NMR spectrum (CDCl3):
6.31 ppm, s.
P
1509 s (C=C); 1377 m (C N); 1196 s (P=N); 592 s,
1H NMR spectrum (CDCl3), , ppm: 5.40 d (1H, NH,
523 s (P Cl). 31P NMR spectrum (CDCl3), P, ppm:
2JPH = 20 Hz), 6.93 m (2H, Harom), 7.09 m (2H,
2
13.62 t (1P, P2, JPP = 48 Hz), 22.59 d (2P, P4, P6,
Harom). 13C NMR spectrum (CDCl3), C, ppm:
1
2JPP = 48 Hz). H NMR spectrum (CDCl3), , ppm:
3
115.10 s (1C), 115.33 s (1C), 122.20 d (1C, JPC
=
5.52 s (1H, NH), 7.07 m (2H, Harom), 7.19 m (2H,
4
Harom). 13C NMR spectrum (CDCl3), C, ppm:
22.8 Hz), 131.77 d (1C, JPC = 2.8 Hz), 157.65 d (1C,
5
2JPC = 9.6 Hz), 160.78 d (1C, JPC = 10 Hz).
3
4
116.78 d (1C, JPC = 22.8 Hz), 123.82 d (1C, JPC
=
15.2 Hz), 123.9 s (1C), 132.69 s (1C), 159.35 d (1C,
The following bacteria and yeast cultures were
used in antibacterial tests: Escherichia coli ATCC
11230, Staphylococcus aureus ATCC 6538, Klebsiella
pneumoniae UC57, Micrococcus luteus La 2971,
Proteus vulgaris ATCC 8427, Pseudomonas
aeruginosa ATCC 27853, Mycobacterium smegmatis
CCM 2067, Bacillus cereus ATCC 7064, Listeria
monocytogenes ATCC 15313, Candida albicans
ATCC 10231, Kluyveromyces fragilis NRRL 2415,
Rhodotorula rubra DSM 70403, Debaryomyces
hansenii DSM 70238, and Hanseniaspora guillier-
mondii DSM 3432. The tests were carried out follow-
ing the disk diffusion technique according to the pro-
cedure outlined by the National Committee for Clinical
Laboratory Standards (NCCLS) [28]. Compounds I,
II, and IV were dissolved in dimethyl sulfoxide
5
2JPC = 2 Hz), 161.78 d (1C, JPC = 2 Hz). Mass spec-
trum, m/z for 35Cl (Irel, %): 425 (25) [M + 3H]+, 422.5
(65) [M]+, 421.7 (100) [M H]+, 386 (35) [M HCl]+,
312 (45) [M NHC6H4F]+. Found, %: C 17.03; H
1.16; N 13.23. C6H5Cl5FN4P3. Calculated, %: C 17.06;
H 1.19; N 13.27.
2,4,4,6,6-Pentachloro-2-(4-chlorophenylamino)-
5
5
5
1,3,5,2 ,4 ,6 -triazatriphosphinine (II) was
synthesized in a similar way from 3.57 g of 4-chloro-
aniline. Yield 3.31 g (54%), white crystals, mp 75 C.
1
IR spectrum (KBr), , cm : 3161 m (N H); 1495 s
(C=C); 1376 m (C N); 1189 s (P=N); 598 s, 526 s
(P Cl). 31P NMR spectrum (CDCl3), P, ppm: 12.88 t
2
2
(1P, P2, JPP = 48 Hz), 22.54 d (2P, P4, P6, JPP
=
1
1
49 Hz). H NMR spectrum (CDCl3), , ppm: 5.59 d
(DMSO) to a concentration of 30 g ml . Empty
2
(1H, NH, JPH = 9.0 Hz), 7.18 m (2H, Harom), 7.38 m
(2H, Harom). 13C NMR spectrum (CDCl3), C, ppm:
122.35 d (1C, JPC = 7.6 Hz), 130.05 s (1C), 130.26 d
(1C, JPC = 2.0 Hz), 135.72 s (1C). Mass spectrum,
sterilized paper disks were impregnated each with
20 l of the above solution. The above-listed bacteria
were incubated for 24 h at 30 0.1 C by inoculation
into Nutrient Broth (Difco), and yeasts were incubated
3
5
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 77 No. 12 2007

2122
YILDIZ et al.
for 48 h on Malt Extract Broth (Difco). An inoculum
containing about 106/ml bacteria cells or 108/ml yeast
cells was spread over Mueller-Minton Agar (Oxoid)
plates (1 ml per plate). The injected disks were placed
on the inoculated agar by pressing slightly and were
incubated for 24 h at 35 C in tests with bacteria or for
72 h at 25 C in tests with yeast cultures. Disks in-
jected with the corresponding reference antibiotic
were applied on each plate for comparison [28, 29].
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ACKNOWLEDGMENTS
The authors are grateful to the Scientific and
Technical Research Council of Turkey, TUBITAK
for financial support of this work [grant no. TBAG-
2159 (102T053)].
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