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Synthesis and antimicrobial studies of bis(O O-dialkyl and alkylene dithiophosphoric acid) adducts of diphenyl diselenide.

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Full Paper
Received: 25 November 2010
Revised: 3 February 2011
Accepted: 3 February 2011
Published online in Wiley Online Library: 20 April 2011
(wileyonlinelibrary.com) DOI 10.1002/aoc.1791
Synthesis and antimicrobial studies
of bis(O,O-dialkyl and alkylene
dithiophosphoric acid) adducts
of diphenyl diselenide
A. A. S. El Khaldya∗ , A. M. Abushanabb and Emad Abu Alkhairc
Dialkyl and alkylene dithiophoshoric acids react with diphenyl diselenide in a 1 : 2 molar ratio in refluxing benzene to
yield Ph2 Se·2 2HS2 P(OR)2 (R = Et, Pr-n, Pr-i, Bu-i and Ph) and Ph2Se2.2HS2POGO , where G = -CH2 CMe2 CH2 -, -CH2 CEt2 CH2 - and
-CMe2 CMe2 -. The complexes are yellow solids (in the cyclic chain) and yellow sticky solids (in the open chain), are soluble in
common organic solvents and are monomeric in nature. They were characterized on the basis of elemental analyses, molecular
weight determinations, IR and NMR (1 H, 13 C and 31 P). The spectral data revealed addition of dithiophosphate moieties to the
diselenide. Studies were conducted to assess the growth-inhibiting potential of some of the synthesized complexes against
c 2011 John Wiley & Sons, Ltd.
various bacterial strains. Copyright Supporting information may be found in the online version of this article.
Keywords: selenium; dithiophosphates; adducts structure
Introduction
As early as 1957 it was shown that selenium is an essential
trace element for animals.[1] Biologists began to investigate
its properties and it was discovered that glutathione peroxidase, a mammalian enzyme, contains a selenocystein residue
in its active site.[2,3] Since then there has also been growing interest in the enzymology and bioorganic chemistry of
selenium.[4 – 6]
Research has been done on compounds with Se–Se bonds,
especially diphenyl diselenide, which is used as a chiral electrophilic selenium reagent for the synthesis of some species of
organic compounds.[7 – 15] Extensive studies with transition metals which make chelating bridges have also been reported.[16,17]
Diphenyl diselenide, which possesses an Se–Se bond as an active site, can be used in nucleophilic and electrophilic as well
as radical reactions by cleavage of the Se–Se bond (PhSe+ ,
•
PhSe− , PhSe ).[7] The formation of complexes of selenium dialkyl and alkylene dithiophosphates is rarely studied.[3,9] Salts
of the acids are often used as ligands. Thus there is a lack of
information concerning the donor properties of these acids as
neutral ligands.[18] In the present paper, we show that dialkyl
and alkylene dithiophosphoric acids react as neutral ligands by
donating a lone pair of electrons and the reaction can take place
without cleavage of the Se–Se bond and the bioactivity of these
complexes.
in 1 : 2 stoichiometry follow equations (1) and (2).
Ph2Se2
+ 2HS2P(OR)2
Ph2Se2.2HS2P(OR)2
(1)
where R = Et, Pr-n, Pr-i, Bu-i and Ph.
Ph2Se2 +
2HS2POGO
Ph2Se2.2HS2POGO
(2)
where G = -CH2 CMe2 CH2 -, -CH2 CEt2 CH2 - and -CMe2 CMe2 -.
The color of the reaction medium changed from orange
to yellow with the progress of the reaction; bis(dialkyl and
alkylene dithiophosphoric acid) adducts of diphenyl diselenide
are yellow sticky solids with open chain acids but yellow solids
with cyclic chain acids. They are soluble in common organic
solvents like benzene, dichloromethane and chloroform. The
molecular weights (Table 1) of all these adducts, determined by
the cryoscopic method in benzene, indicated their monomeric
nature.
∗
Correspondence to: A. A. S. El Khaldy, PO Box 322 Department of Chemistry,
Room 409, Alabama A&M University, Normal, AB 35762, USA.
E-mail: adnan.elkhaldy@aamu.edu
a PO Box 322 Department of Chemistry, Room 409, Alabama A&M University,
Normal, AB 35762, USA
Results and Discussion
b Chemistry Department, Al-Aqsa University, Gaza, Palestine
Appl. Organometal. Chem. 2011, 25, 491–496
c PO Box 2177, Chemistry Department, Al-Azhar University, Gaza, Palestine
c 2011 John Wiley & Sons, Ltd.
Copyright 491
The reactions of diphenyl diselenide with dialkyl and alkylene
dithiophosphoric acids in refluxed benzene with constant stirring
A. A. S. El Khaldy, A. M. Abushanab and E. A. Alkhair
Table 1. Physical properties and analytical data of bis(dialkyl and alkylene dithiophosphoric acid) adducts of diphenyl diselenide compounds
SI no. Compounds
Melting Molecular weight,
point (◦ C) found (calculated)
Physical state
%S, found
(calculated)
%Se, found
(calculated)
%C, found
(calculated)
%H, found
(calculated)
1
Ph2 Se2 ·2HS2 P(OEt)2
C20 H32 P2 O4 S4 Se2
Yellow sticky solid
–
681 (684.57)
17.54 (18.73) 22.23 (23.06) 35.11 (35.09)
4.88 (4.71)
2
Ph2 Se2 ·2HS2 P(OPr-n)2
C24 H40 P2 O4 S4 Se2
Yellow sticky solid
–
737 (740.68)
16.46 (17.31) 20.53 (21.32) 38.76 (38.91)
5.53 (5.44)
3
Ph2 Se2 ·2HS2 P(OPr-i)2
C24 H40 P2 O4 S4 Se2
Yellow sticky solid
–
734 (740.68)
16.48 (17.31) 20.89 (21.32) 38.69 (38.91)
5.62 (5.44)
4
Ph2 Se2 ·2HS2 P(OBu-i)2
C28 H48 P2 O4 S4 Se2
Yellow sticky solid
–
798 (796.79)
15.25 (16.09) 18.94 (19.81) 42.34 (42.20)
6.21 (6.07)
5
Ph2 Se2 ·2HS2 P(OPh)2
C36 H32 P2 O4 S4 Se2
Yellow sticky solid
–
872 (876.75)
15.34 (14.62) 17.32 (18.01) 49.48 (49.31)
3.79 (3.67)
Yellow solid
61
711 (708.61)
17.62 (18.09) 21.12 (22.28) 37.29 (37.29)
4.63 (4.55)
Yellow solid
58
763 (764.70)
15.89 (16.76) 19.76 (20.65) 40.82 (40.83)
5.15 (5.27)
Yellow solid
47
733 (736.65)
16.57 (17.40) 20.67 (21.43) 39.33 (39.13)
4.97 (4.92)
6
C22 H32 P2 O4 S4 Se2
7
C26 H40 P2 O4 S4 Se2
8∗∗∗
Ph2Se2·2HS2POCMe2CMe2O
C24 H36 P2 O4 S4 Se2
•
Molecular weight = K W/T × W × 100; %S = 32/234 weight of precipitate formed/weight of compound taken × 100; %C and %H, A = mass of A in
the whole compound/mass of whole compound × 100.
Table 2. IR spectral data (cm−1 ) of bis(dialkyl and alkylene dithiophosphoric acid) adducts of diphenyl diselenide compounds
SI no.
Compound
1
2
3
4
5
6
Ph2 Se2 ·2HS2 P(OEt)2
Ph2 Se2 ·2HS2 P(OP-n)2
Ph2 Se2 ·2HS2 P(OPr-i)2
Ph2 Se2 ·2HS2 P(OBu-i)2
Ph2 Se2 ·2HS2 P(OPh)2
ν(P)–O–C
νP–O–(C)
Ring vibration
νP S
1014.5
1055.0
975.9
999.1
1182.0
1041.0
850.5
862.1
893.0
867.9
923.8
819.7
–
–
–
–
–
983.6 s
669.3
688.5
667.3
665.4
688.5
603.7
s
s
s
s
s
s
m
m
m
s
s
s
νP–S
s
s
s
s
s
s
507.2
515.0
516.9
530.0
518.8
553.5
νS–H
m
m
m
m
m
s
2401.2
2401.0
2401.2
2400.0
2403.1
2543.9
ν(Se–S)
m
m
m
mb
m
mb
370.1
370.0
371.3
369.0
372.1
375.0
m
m
w
m
w
m
7
1068.0 s
823.5 m
993.3 s
605.6 s
513.0 m
2538.1 m
377.5 w
8
1018.3 m
848.6m
931.6 s
659.6m
588.2 m
2524.6 m
374.2 m
Ph2Se2·2HS2POCMe2CMe2O
IR Spectra
492
The assignments of some important IR frequencies are given in
Table 2. Two bands of strong intensities present in the regions
1182–976 and 893–820 cm−1 may be assigned to ν(P)–O–C
and νP–O–(C) vibrations, respectively.[19,20] Strong bands due to
dioxaphospholane and dioxaphosphorinane ring vibrations are
present in the region 993–931 cm−1 and these are probably
coupled with C–C stretching vibrations.[21,22] A sharp band
present in the region 688–665 cm−1 can be assigned to νP S
vibrations.[20,23 – 25] This shows notable shifting ( = 22.7 cm−1 )
towards higher frequencies in open chain derivatives, but
in the cyclic chain derivatives the shifts are towards lower
frequencies (by = 59.1 cm−1 ) compared with the free acids.
This shift is probably due to coordination of sulfur of the
P S group to the selenium atom. The bands of medium
intensities in the region 588–507 cm−1 may be attributed to
νP–S vibrations.[24,25]
The bands of medium intensities in the region 2544–2400 cm−1
are due to S–H vibrations.[26] This shows notable shifting
wileyonlinelibrary.com/journal/aoc
( = 64.5 cm−1 ) towards lower frequencies in the open
chain, but in the cyclic chain there is no shift observed
with respect to its position in the free acids and a new
band is observed in the region 377–369 cm−1 due to Se–S
vibrations.[27,28]
1 H NMR Spectra
The1 H NMR spectra (Table 3) of these adducts show the characteristic proton resonance of the corresponding dialkyl protons as
well as alkylene protons. The S–H protons were observed in the
range 2.60–4.02 ppm;[26] a small shift (of ∼0.189 ppm) was also
noted in comparison to its position in the parent acids.[18] This
small chemical shift means that the ligands behaves as a neutral
acid (addition reaction). Complex multiplets due to the protons
of phenyl groups attached to the selenium atoms were present
at 6.82–7.72 ppm.[17] The signal of hydrogen atom, present at the
α-carbon atom of the P–O–C skeleton of alkyl and alkylene chains,
became doubled owing to coupling with 31 P.
c 2011 John Wiley & Sons, Ltd.
Copyright Appl. Organometal. Chem. 2011, 25, 491–496
Synthesis and antimicrobial studies of adducts of diphenyl diselenide
Table 3.
1
H and 31 P NMR spectral data of bis (dialkyl and alkylene dithiophosphoric acid) adducts of diphenyl diselenide compounds
31
P chemical shift in
δ ppm (parent acid)
SI no.
Compounds
1 H chemical shift in δ
1
Ph2 Se2 ·2HS2 P(OEt)2
1.38, t (J = 7 Hz) 12H (-CH3 )
2.60, s, 2H (SH)
4.20–4.30, q, 8H (-OCH2 )
7.20–7.35, m, 10H (C6 H5 )
86.5 (85.7)
2
Ph2 Se2 ·2HS2 P(OPr-n)2
1.05, t (J = 7 Hz) 12H (-CH3 )
1.65–1.75, m, 8H (-CH2 )
3.02, s, 2H (SH)
4.10–4.19, t, 8H (-OCH2 )
7.23–7.62, m, 10H (C6 H5 )
86.8 (86.1)
3
Ph2 Se2 ·2HS2 P(OPr-i)2
1.39, d (J = 6 Hz) 24H (-CH3 )
3.10, s, 2H (SH)
4.85–4.98, m, 4H (-OCH)
7.25–7.63, m, 10H (C6 H5 )
83.0 (82.3)
4
Ph2 Se2 ·2HS2 P(OBu-i)2
0.99, d (J = 7 Hz) 24H (-CH3 )
1.89–2.15, m, 4H (-CH)
3.07, s, 2H (SH)
3.91–4.00, d (J = 15.6 Hz) 8H (-OCH2 )
7.23–7.72, m, 10H (C6 H5 )
86.9 (85.7)
5
Ph2 Se2 ·2HS2 P(OPh)2
4.02, s, 2H (SH)
6.82–7.72, m 30H (C6 H5 and OC6 H5 )
80.2 (79.9)
6
1.12, s, 12H (CH3 )
2.80, s, 2H (SH)
4.09, d (J = 15.6 Hz) 8H (-OCH2 )
7.25–7.60, m, 10H (C6 H5 )
91.2 (77.3)
7
0.92, t (J = 6 Hz) 12H (-CH3 )
1.47–1.55, q, 8H (CH2 )
2.82, s, 2H (SH)
4.14, d (J = 15.3 Hz) 8H (-OCH2 )
7.24–7.62, m, 10H (C6 H5 )
79.1 (78.5)
1.49, s, 24H (CH3 )
3.61, s, 2H (SH)
7.26–7.74, m, 10H (C6 H5 )
94.0 (93.1)
8
Ph2Se2·2HS2POCMe2CMe2O
ppm in CDCl3
s = singlet, d = doublet, t = triplet, q = quartet m = multiplet.
13 C NMR Spectra
Structural Elucidation
13 C
NMR spectra of the parent dithio acids and a few
The
representative complexes were recorded in deutarated chloroform
at ambient temperature (Table 4). In the spectra of these
complexes four signals for phenyl carbons were observed in the
region 131.9–128.1 ppm for C1 , C2,6 , C3,5 and C4 , respectively.[17]
The appearance of a single set for the carbon atoms of the phenyl
groups showed their equivalent nature. The signals for dialkyl and
alkylene carbons were observed at the expected positions.
31 P NMR Spectra
Appl. Organometal. Chem. 2011, 25, 491–496
Experimental
Stringent precautions were taken to exclude moisture. Solvents
(benzene, n-hexane) were dried by standard methods. Glycols
c 2011 John Wiley & Sons, Ltd.
Copyright wileyonlinelibrary.com/journal/aoc
493
The proton-decoupled 31 P NMR spectra (Table 3) showed only
one signal for each adduct in the region 94.03–79.20 ppm. There
was a very small shift of the signal towards a higher field
(∼0.76–1.25 ppm) from its position in the corresponding acid,
except for the neopentylene derivatives, which possessed a large
shift (∼13.93 ppm) towards a higher field; this was probably due
to a dative P S → M bonding.
Phosphorus–31 NMR spectra showed magnetic equivalence
of the phosphorus nuclei in the complexes. The shift in the
position of the peak due to P S in the IR spectra showed that
the donor center in the acid molecule was phosphorothionyl
sulfur.
The molecular weight data also provide supporting evidence.
The presence of SH groups in 1 H NMR and IR proves that these
ligands behaved as neutral ligands.
Attempts to obtain suitable crystals for x-ray diffraction study
have so far been unsuccessful. From the above data a plausible
structure of the following type may be suggested for the new
derivatives (Figs 1 and 2).
A. A. S. El Khaldy, A. M. Abushanab and E. A. Alkhair
Table 4.
13
C NMR spectral data of some bis(dialkyl and alkylene dithiophosphoric acid) adducts of diphenyl diselenide compounds (δ ppm)
Ph2 Se2 carbons
Dialkyl and alkylene
dithiophosphate
C1
C2,6
C3,5
C4
Ph2 Se2 ·2HS2 P(OEt)2
131.9
131.3
129.6
128.
15.57 (s, CH3 )
59.50 (s, OCH2 )
2
Ph2 Se2 ·2HS2 P(OPr-n)2
131.9
131.3
129.6
128.
10.03 (s, CH3 )
22.78(s, CH2 )
65.55(s, OCH2 ).
3
Ph2 Se2 ·2HS2 P(OPr-i)2
131.9
131.3
129.6
128.
23.36 (s, CH3 )
73.77 (s OCH)
4
Ph2 Se2 ·2HS2 P(OBu-i)2
131.9
131.3
129.7
128.1
19.20 (s, CH3 )
29.15 (s, CH)
74.40 (s, OCH2 )
5
Ph2 Se2 ·2HS2 P(OPh)2
131.9
131.3
129.6
128.
121.47 s, CH; 129.34(s, CH)
150.34 (s, OC)
6
131.9
131.3
129.6
128.1
21.90 (s, CH3 )
32.94 (s, C)
78.30 (s, OCH2 )
7
131.9
131.3
129.6
128.
7.14 (s, CH3 )
23.02 (s, CH2 )
37.24 (s, C-Et)
74.31 (s, OC)
131.9
131.3
129.6
128.1
24.40 (s, CH3 )
91.20 (s, OC)
SI no.
Compound
1
8
Ph2Se2·2HS2POCMe2CMe2O
Figure 1. Structure of bis(O,O -dialkyldithiophosphoric acid) adducts of
diphenyl diselenide, where R = Et, Pr-n, Pr-i, Bu-i and Ph.
494
were distilled before use; diphenyl diselenide (Merck) was used
as received. Dialkyl and alkylene dithiophosphoric acids were
prepared by the reaction of phosphorus pentasulfide and alcohols
in a 1 : 4 ratio, and in a 1 : 2 ratio with glycols as described
in the literature.[18,28] Sulfur was determined by Messenger’s
method as barium sulfate. Selenium was determined by iodometric
titration.
Infrared spectra were recorded as Nujol mulls using CsI cells
in the region 4000–200 cm−1 on an FT-IR 8201PC spectrophotometer. 1 H and 13 C spectra were recorded on a Jeol-FT NMR
spectrometer-LA300 and using TMS as the internal reference.31 P
NMR spectra were recorded in CHCl3 using H3 PO4 as an external
reference on the same instrument. The following synthetic details for a specific 1 : 2 reaction represent the procedure used to
synthesize all compounds.
wileyonlinelibrary.com/journal/aoc
Figure 2. Structure of bis(alkylenedithiophosphoric acid) adducts of
diphenyl diselenide where G = -CH2 CMe2 CH2 -, -CH2 CEt2 CH2 - and CMe2 CMe2 -.
Reaction between Diphenyl Diselenide with Dialkyl (OEt)
Dithiophosphoric Acid in 1 : 2 Molar Ratio
A benzene (∼10 ml) solution of HS2 P(OEt)2 (0.836 g, 3.58 mmol)
was added to a benzene (∼15 ml) solution of Ph2 Se2 (0.614 g,
1.79 mmol) dropwise with stirring at room temperature. The
reaction mixture was refluxed for ∼5 h, during which the color of
the reaction mixture changed from orange to yellow. The excess
solvent was removed under reduced pressure and the product
washed repeatedly by n-hexane; the desired product was finally
dried under reduced pressure (1.08 g, 88.52%).
Reaction between Diphenyl Diselenide with Alkylene
Dithiophosphoric Acids in 1 : 2 Molar Ratio
A neopentylene dithiophosphoric acid (0.873 g, 4.40 mmol)
solution in benzene (∼10 ml) was added to a benzene (∼15 ml)
c 2011 John Wiley & Sons, Ltd.
Copyright Appl. Organometal. Chem. 2011, 25, 491–496
Synthesis and antimicrobial studies of adducts of diphenyl diselenide
Table 5. Inhibition zones (mm) obtained with bis(dithiophosphoric acid) adduct of diphenyl diselenide complexes
Inhibition zones (mm)
SI. no.
Compound
Concentration (mol/l)
S. aurous
E. coli
1
0.0287 (C1)
0.0692 (C2)
0.0882 (C3)
0.1110 (C4)
8
16
18
19
6
13
16
17
2
0.0215 (D1)
0.0340 (D2)
0.0442 (D3)
0.0566 (D4)
4
9
10
12
Negative
Negative
4
6
solution of Ph2 Se2 (0.687 g, 2.20 moml) dropwise in a 2 : 1 ratio
with stirring at room temperature. The mixture was refluxed
for ∼5 h. The color of the reaction changed to yellow. The
excess solvent was removed under reduced pressure and the
product washed repeatedly with n-hexane; the desired product
was finally dried under reduced pressure (1.48 g, 95.4%; m. p.
61 ◦ C).
Bioactivity Test of bis(Dithiophosphoric Acid) Adducts
of Diphenyl Diselenide
The antimicrobial activity of the bis(neopentylene and 2,2-diethyl
propane-1,3-diol dithiophosphoric acid) adducts of diphenyl
diselenide were determined by the agar diffusion method.
Sterile nutrient agar was inoculated with test organisms being
locally isolated strains of Staphylococcus aureus and Escherichia
coli. Each 100 ml of the medium received 1 ml of 24 h broth
culture.
Aliquots of 50 µl of the two tested compound solutions in water
and having different concentrations were placed separately in
cups (8 mm diameter) cut into the agar medium. The plates were
incubated at 37 ◦ C for 24 h. The resulting inhibition zones were
measured and the results are presented in Table 5.
The bis(neopentylene dithiophosphoric acid) adducts of
diphenyl diselenide had a greater antimicrobial effect than
bis(2,2-diethyl propane-1,3-diol dithiophosphoric acid) adduct of
diphenyl diselenide against S. aureus (Gram-positive) and E. coli
(Gram-negative) bacteria in different concentrations of the two
adducts. The results showed that the increase in the concentration
of bis(neopentylene dithiophosphoric acid) adducts of diphenyl
diselenide increased the inhibition zones, although the differences
in the concentrations of C2, C3 and C4 were small. The concentration showing the best antimicrobial effect on the plates among
the different bis(neopentylene dithiophosphoric acid) adducts of
diphenyl diselenide was C2.
On the other hand, bis(2,2-diethylpropane1,3diol dithiophosphoric acid) adduct of diphenyl diselenide also had an antimicrobial effect against S. aureus and E. coli bacteria. The lower
concentrations (D1 and D2) had no effect on inhibition zones, but
higher concentrations (D3 and D4) did show an effect.
Conclusions
Appl. Organometal. Chem. 2011, 25, 491–496
Acknowledgments
One of the authors (A. A. S. Elkhaldy) is grateful to the SRF,
New York, USA for their financial assistance. I also would like to
thank Professor Malcom Chisholm at OSU and Professor Matthew
Edwards at AAMU for their assistance and support.
Supporting information
Supporting information may be found in the online version of this
article.
References
[1] K. Schwarz, C. M. Foltz. J. Am. Chem. Soc. 1957, 79, 3292.
[2] L. Flohe, W. A. Gunzler, H. H. Schock, FEBS Lett. 1973, 32, 132.
[3] J. T. Rotruck, A.L. Pope, H. E. Ganther, A. B. Swanson, D. G. Hafeman,
W. G. Hoekstra. Science 1973, 179, 588.
[4] G. N. Schrauzer, Selen. Neue Entwicklungen aus Biologie, Biochemie
und Medizin, Johann Ambrosius Barth: Heidelberg, 1998, 232.
[5] X. Zhang, H. P. Xu, Z. Y. Dong, Y. P. Wang, J. Q. Liu, J. C. Shen., J. Am.
Chem. Soc. 2004, 126, 10556.
[6] N. Ma, Y. Li, H. Xu, Z. Wang, X. Zhang, J. Am. Chem. Soc.2010, 132,
442.
[7] K. C. Nicolaou, N. A. Petasis, Selenium in Natural Products Synthesis,
CIS: Philadelphia, PA, 1984, p. 66.
[8] C. Paulmier, Selenium Reagents and Intermediates in Organic
Synthesis, Pergamon Press: Oxford, 1986, Chaps VII and VIII.
[9] L. A. Wessjohann, U. Sinks, J. Prakt. Chem. 1998, 340, 189–203.
[10] K. Hiroi, Y. Suzuki, I. Abe, Tetrahedron Asymm. 1999, 10, 1173.
[11] T. Billard, B. R. Langlois, Tetrahedron Lett. 1996, 7, 6865.
[12] F. Nief, Coord. Chem. Rev. 1998, 13 and 178.
[13] J. Lee, M. Brewer, M. Berardini, J. G. Brennan, Inorg. Chem. 1995, 34,
3215.
[14] L. Awwal, J. E. Drake, M. B. Hursthouse, R. Kumar, M. E. Light,
R. Ratnani, K. Saraswat, Polyhedron 2007, 26, 3973.
[15] A. L. Bingham, J. E. Drake, M. B. Hursthouse, M. E. Light, M. Nirwan,
R. Ratnani, Polyhedron 2007, 26, 2672.
[16] I. Edith I. D. Koffi-Sokpa, T. Calfee, B. R. T. Allred, J. L. Davis,
E. K. Haub, A. K. Rich, R. A. Porter, M. S. Mashuta, J. F. Richardson,
M. E. Noble, Inorg. Chem. 1999, 38(4), 802.
[17] S. K. Srivastava, S. Tomar, R. Rastogi, R. Saxena, Phosphorus Sulfur
Silicon Relat Elem. 2010, 185, 634.
[18] H. P. S Chauhan, C. P. Bhasin. G Srivastava, R. C Mehrotra, Phosphorus
Sulfur 1983, 15, 99.
[19] B. P. Singh. G. Srivastava, R. C. Mehrotra, Organomet. Chem. 1979,
171, 35.
c 2011 John Wiley & Sons, Ltd.
Copyright wileyonlinelibrary.com/journal/aoc
495
In conclusion, we have shown the facile synthesis of dithiophosphate derivatives of selenium. All these new compounds were
characterized using multinuclear NMR, IR and elemental analyses.
We showed that dialkyl and alkylene dithiophosphoric acids react
as neutral ligands by donating a lone pair of electrons, and that
the reaction can take place without cleavage of the Se–Se bond.
These complexes have important bioactivity.
A. A. S. El Khaldy, A. M. Abushanab and E. A. Alkhair
[20]
[21]
[22]
[23]
J. Casdeon, W. N. Baxter, W. De Acetis. J. Org. Chem. 1959, 24, 247.
R. A. V. Jones, A. R. Katritzky, J. Chem. Soc. 1960, 4367.
D. E. C. Corbridge, Top. Phosphorus Chem. 1969, 6, 235.
L. Pavia, G. M. Lampman, G. S. Kris, Introduction to Spectroscopy, 2nd
edn, 1996, pp. 42 and 80.
[24] C. Alyea, B. S. Ramaswamy, A. N. Bhat, R. C. Fay, Inorg. Nucl. Chem.
Litt. 1973, 9, 399.
[25] R. Beattie, Q. Rev. 1963, 17, 382.
[26] R. K. Gupta, A. K. Rai, R. C. Mehrotra, V. K. Jain, P. F. Hoskins,
E. R. T. Tiekink, Inorg. Chem., 1985, 24, 3280.
[27] J. N. Pandey, G. Srivastava, J. Indian Chem. 1986, 9, 41.
[28] T. W. Mastin, G. R. Norman, E. A. Wellmuenster, J. Am. Chem., Soc.
1945, 67, 1662.
496
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acid, adduct, synthesis, diseleniden, alkylenen, antimicrobials, dithiophosphoric, dialkyl, bis, studies, diphenyl
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