New organic derivatives of O,O'-(o-, m-, and p-ditolyl)/ dibenzyldithiophosphates: Synthesis and characterization

Article abstract of DOI:10.1080/10426500802445340

Reactions of (m- and p-ClC₆H₄NH₂), (p-BrC₆H₄NO₂), and (p-ClCOC₆H ₄NO₂) with sodium O,O'-ditolyl/ dibenzylphosphorodithionates, (ArO)₂PS₂

Full text of DOI:10.1080/10426500802445340

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Phosphorus, Sulfur, and Silicon
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New Organic Derivatives of
O,O′-(o-, m-, and p-Ditolyl)/
Dibenzyldithiophosphates:
Synthesis and Characterization
Sangeeta Sharma a , Suresh Magotra a & Sushil K.
Pandey a
a Department of Chemistry , University of Jammu ,
Jammu, India
Published online: 22 Jul 2009.
To cite this article: Sangeeta Sharma , Suresh Magotra & Sushil K. Pandey (2009)
New Organic Derivatives of O,O′-(o-, m-, and p-Ditolyl)/Dibenzyldithiophosphates:
Synthesis and Characterization, Phosphorus, Sulfur, and Silicon and the Related
Elements, 184:8, 2140-2151, DOI: 10.1080/10426500802445340
To link to this article: http://dx.doi.org/10.1080/10426500802445340
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Phosphorus, Sulfur, and Silicon, 184:2140–2151, 2009
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500802445340
New Organic Derivatives of O,Oꢀ-(o-, m-, and
p-Ditolyl)/Dibenzyldithiophosphates: Synthesis and
Characterization
Sangeeta Sharma, Suresh Magotra, and Sushil K. Pandey
Department of Chemistry, University of Jammu, Jammu, India
Reactions of (m- and p-ClC H NH ), (p-BrC H NO ), and (p-ClCOC H NO )
6
4
2
6
4
2
6
4
2
with sodium O,Oꢀ-ditolyl/dibenzylphosphorodithionates, (ArO) PS Na, (Ar =
2
2
o−, m−, and p−CH C H or –C H CH ) in 1:1 molar ratio in refluxing
3
6
4
6
5
2
toluene under anhydrous conditions resulted in the formation of the compounds
(ArO) PS C H L and (ArO) PS COC H L (L = NH or NO ) in 87–94% yield.
2
2
6
4
2
2
6
4
2
2
These viscous compounds were characterized by elemental analyses, molecular
1
13
31
weight determination, and IR and NMR ( H, C, and P) spectroscopic stud-
ies, which revealed a monodentate mode of bonding of the dithiophosphate moiety
with the carbon of the phenyl ring of the organic moiety leading to a P–S–C linkage.
Keywords Dithiophosphate; organophosphorus; phosphorodithioate; phosphorus–
sulfur
INTRODUCTION
Dialkylphosphonates [(RO)2PO]−, dialkyldithiophosphonates [(RS)2
PO]−, dialkyldithiophosphates [(OR)2PS2]−, and O, Oꢀ-alkylenedithio-
phosphates, [OGOPS2]− (where G = CHMeCMMe-, CMe2CMe2-,
CH2CMe2CH2-, CH2CEt2CH2-, and CHMeCH2CMe2-), have at-
tracted wide attention in academia, especially due to their versatile
utility as active pesticides1–2 and also for providing various bond-
ing aspects with several metals and metalloids.3–6 These derivatives
find extensive applications in agriculture,7–8 industry,9–10 and ana-
lytical studies.11–12 A variety of complexes have been reported with
these ligands, in which they have predominantly exhibited a biden-
tate mode of bonding.13–19 However, the less common monodentate
Received 13 May 2008; accepted 2 September 2008.
We are grateful to the Central Drug Research Institute, Lucknow, for providing spec-
tral studies.
Address correspondence to Sushil K. Pandey, Department of Chemistry, Univer-
sity of Jammu, Baba Saheb Ambedkar Road, Jammu, 180 006 (J & K), India. E-mail:
kpsushil@rediffmail.com
2140

Derivatives of Dibenzyldithiophosphates
2141
linkage has also been depicted by these ligands, such as in the case
of nickel and tin.20–21 A literature survey revealed scant information
on the derivatives of O,Oꢀ-ditolyldithiophosphate ligands compared to
dialkyl- and alkylenedithiophosphates.22–26 We have recently reported
a convenient synthesis of ditolyldithiophosphate ligands27 and also
a single crystal X-ray structure of [Et3NH]+[(o-MeC6H4O)2PS2]−.28
These new ditolyldithiophosphate ligands appear to be potential chelat-
ing ligands to the metals, metalloids, and nonmetals. Recently, some
metal complexes with the ditolyldithiophosphate ligands have been
synthesized and characterized.29–30 Some interesting applications
of ditolyldithiophosphates have also been reported such as rubber
vulcanizers,31 aerofloats,32 polymerization catalysts,33 oil additives,34
and acaricides.35 The nitrogen-containing organodithiophosphates are
well known biologically active compounds, such as methyl/ethyl
parathion, (RO)2P(S)OC6H4NO2 (R = Me/Et), and others such as
malathion, (MeO)2PS(S)CHCO2EtCH2CO2Et, which is produced from
dialkyldithiophosphoric acids, (RO)2PS2H (R = Me/Et) and widely used
as effective pesticides.35–36 A review of the literature indicated no
report of organic derivatives of ditolyl/dibenzyldithiophosphates. In
view of the above interesting facets of dithiophosphate chemistry, it
was thought worthy to investigate the chemistry of organic deriva-
tives of O,Oꢀ-(o-, m-, and p-ditolyl)/dibenzyldithiophosphates. So, we
report herein on the synthesis of some new nitrogen containing organic
compounds of O,Oꢀ-ditolyl/dibenzyldithiophosphates using m- and p-
chloroaniline, p-bromonitrobenzene, and p-nitrobenzoylchloride.
RESULTS AND DISCUSSION
Reactions of m-ClC6H4NH2, p-ClC6H4NH2, p-BrC6H4NO2, and p-
ClCOC6H4NO2 with sodium O,Oꢀ-(o-, m- and p-ditolyl)/dibenzyl phos-
phorodithioates, (ArO)2PS2Na (Ar = o-, m-, and p-CH3C6H4 and –
C6H5CH2) in 1:1 molar ratio in toluene under refluxing conditions
resulted in the formation of compounds of the type (ArO)2PS2C6H4L
(L = m-NH2 for 1–4, p-NH2 for 5–8, and p-NO2 for 9–12) and
(ArO)2PS2COC6H4-p-NO2 (13–16) in 87–94% yield (Scheme 1).
These reactions were found to be a bit sluggish and needed to be
refluxed for 9–11 h. These compounds are viscous liquids; they appear
to be moisture sensitive, since they became turbid when left open in
humid atmosphere; and they are soluble in organic solvents such as
toluene, benzene, and chloroform and insoluble in carbon tetrachloride
and n-hexane. The micro-elemental analyses (C, H, N, and S) were
found to be in agreement with the molecular weight of the compound.

2142
S. Sharma et al.
SCHEME 1 Where Ar = o-, m- and p-CH3C6H4 or C6H5CH−2 ; L = m-NH2 (1–4),
p-NH2 (5–8) and p-NO2 (9–12) and p-NO2 (13–16); X = Cl or Br.
These compounds are nonvolatile even under reduced pressure, and
they decomposed to dark brown products, which could not be character-
ized. The monomeric nature of these compounds was confirmed by their
molecular weight determination using a cryoscopic method (Table I).
Mechanistically, the reaction between dithiophosphate ligand and
organic moiety might involve the nucleophilic displacement of the
halide ion from the organic moiety with the dithiophosphate ligand
(Scheme 2).
The IR spectral data (4000–400 cm−1) were interpreted by compari-
son with relevant and related literature reports.22–25,34 The IR spectra
of these compounds show the disappearance of the νC X (X CI and Br)
absorption band present in the range of 755–710 cm−1 in the parent
organic moiety and the appearance of a new absorption band in the
region 680–608 cm−1, which is assigned for νC S vibrations. This fact
has supported the cleavage of C X bond thereby formation of P(S)–S–C
linkage in these compounds. The bands of medium intensities in the
region 780–681 cm−1 and 598–506 cm−1 are attributed to νP S and
νP–S (asymmetric and symmetric) vibrations of the dithiophosphate
moiety, which indicated no shifting compared to the parent dithio lig-
and. The absorption bands of strong intensity present in the region
1195–1170 cm−1 and 958–817 cm−1 are assigned for ν(P)–O–C and νP–
O–(C) stretching vibrations, respectively. A band forνN–H vibrations
was observed in the region 3473–3339 cm−1 in the compounds 1–8. The
absorption band for nitro group in the compounds 9–16 was observed
SCHEME 2 Nucleophilic displacement of halide ion with dithiophosphate
moiety.

2143

2144

Derivatives of Dibenzyldithiophosphates
2145
TABLE II IR Spectral Data of Organic Derivatives of Ditolyl/
dibenzyldithiophosphates (in cm−1
)
S. Aromatic
No. ν(C—H) ν(P)—O—C νP—O—(C) νP
S νP—S νC—S νN—H νNO νC O
1. 2962, b
2. 2956, b
3. 3058, b
4. 2963, b
5. 2961, b
6. 2963, b
7. 2963, b
8. 2971, b
9. 2964, b
10. 2967, b
11. 2965, b
12. 2967, b
13. 2964, b
14. 2963, b
15. 2924, b
16. 2963, b
1174, s
1174, s
1195, s
1170, s
1191, s
1177, s
1181, s
1174, s
1188, s
1190, s
1177, s
1188, s
1181, s
1192, s
1189, s
1171, s
889, s
887, s
888, s
889, s
896, s
877, s
820, s
817, s
870, s
885, s
880, s
885, s
951, s
958, s
942, s
926, s
682, m 563, m 608, m 3343, b
681, m 559, m 632, m 3339, b
681, m 527, m 630, m 3364, b
682, m 561, m 668, m 3387, b
688, m 562, m 640, m 3416, b
681, m 566, m 635, m 3387, b
697, m 506, m 639, m 3473, b
698, m 585, m 637, m 3385, b
—
—
—
—
—
—
—
—
—
—
—
–
—
—
—
—
—
—
—
—
780, m 510, m 665, m
775, m 514, m 665, m
760, m 511, m 640, m
766, m 513, m 680, m
705, m 598, m 669, m
684, m 588, m 641, m
730, m 591, m 631, m
699, m 598, m 670, m
—
—
—
—
—
—
—
—
1150, s
1164, s
1166, s
1205, s
1190, s 1580, s
1234, s 1610, s
1421, s 1609, s
1478, s 1592, s
Where s = Strong, b = broad, and m = medium.
in the region 1478–1150 cm−1. The relevant IR spectral data are data
are given in Table II.
In the 1H NMR spectra (in CDCl3), the chemical shifts for the −CH3
and −CH2 (benzyl ring) protons were observed in the regions δ 2.2–
2.3 and δ 3.5–3.6 ppm as a singlet, whereas the chemical shift for
the phenyl ring protons of the dithio moiety appeared in the region δ
7.0–7.5 ppm as a multiplet in all the compounds. This multiplet was
due to long range coupling of these protons with a magnetically active
phosphorus atom. The chemical shifts for the phenyl protons of organic
moiety (–C6H4NH2, −C6H4NO2, and –COC6H4NO2) also appeared as
multiplet in the range δ 6.5–7.1 ppm. The resonance for –NH2 protons
in the compounds 1–8 was observed as a singlet in the region δ 3.0–3.5
1
ppm. The H NMR spectral data of these compounds are summarized
in Table III.
The 31P NMR chemical shift occurred as singlet in the range δ 81.0–
88.6 ppm for these compounds. The upfield shifting of 31P chemical
shift in range of δ 20–25 ppm compared to the parent dithiophosphate
moiety (∼δ 105 ppm) might be due to the formation of a covalent linkage
between the carbon and sulfur atom of the dithiophosphate moiety in
a unidentate manner. The occurrence of only one singlet in each case
might be due to the equivalent nature of the phosphorus atom in these

2146
S. Sharma et al.
TABLE III 1H and 31P NMR Spectral Data of Organic Derivatives of
Ditolyl/dibenzyldithiophosphates in CDCl3 (δ ppm)
S. No.
1.
1H
31P
2.3 (s, 6H, –CH3), 7.0–7.3 (m, 8H, –C6H4), 6.8–6.9 (m, 4H, –C6H4
of C6H5NH2), 3.5 (s, 2H, –NH2)
84.8, s
2.
3.
2.3 (s, 6H, –CH3), 7.1–7.2 (m, 8H, –C6H4), 6.5–6.6 (m, 4H, –C6H4
of C6H5NH2), 3.5 (s, 2H, –NH2)
2.2 (s, 6H, –CH3), 7.0–7.2 (m, 8H, –C6H4), 6.5–6.6 (m, 4H, –C6H4
of C6H5NH2), 3.5 (s, 2H, –NH2)
3.5 (s, 6H, –CH2), 7.2–7.3 (m, 10H, –C6H5), 6.7–6.9 (m, 4H, –C6H4
of C6H5NH2), 3.5 (s, 2H, –NH2)
2.2 (s, 6H, –CH3), 7.2–7.3 (m, 8H, –C6H4), 6.7–6.9 (m, 4H, –C6H4
of C6H5NH2), 3.5 (s, 2H, –NH2)
2.2 (s, 6H, –CH3), 7.1–7.2 (m, 8H, –C6H4), 6.7–6.9 (m, 4H, –C6H4
of C6H5NH2), 3.4 (s, 2H, –NH2)
2.2 (s, 6H, –CH3), 7.1–7.3 (m, 8H, –C6H4), 6.7–6.9 (m, 4H, –C6H4
of C6H5NH2), 3.4 (s, 2H, –NH2)
3.5 (s, 6H, –CH2), 7.1–7.3 (m, 10H, –C6H5), 6.7–6.9 (m, 4H, –C6H4
of C6H5NH2), 3.0 (s, 2H, –NH2)
2.2 (s, 6H, –CH3), 7.0–7.4 (m, 8H, –C6H4), 6.6–6.9 (m, 4H, –C6H4
of C6H5NO2)
2.2 (s, 6H, –CH3), 7.1–7.3 (m, 8H, –C6H4), 6.6–6.9 (m, 4H, –C6H4
of C6H5NO2)
2.3 (s, 6H, –CH3), 7.2–7.5 (m, 8H, –C6H4), 6.6–6.9 (m, 4H, –C6H4
of C6H5NO2)
3.5 (s, 6H, –CH2), 7.1–7.3 (m, 10H, –C6H5), 6.6–6.8 (m, 4H, –C6H4
of C6H5NO2)
2.3 (s, 6H, –CH3), 7.2–7.3 (m, 8H, –C6H4), 6.8–7.0 (m, 4H, –C6H4
of COC6H5NO2)
2.3 (s, 6H, –CH3), 7.0–7.2 (m, 8H, –C6H4), 6.8–7.0 (m, 4H, –C6H4
of COC6H5NO2)
2.2 (s, 6H, –CH3), 7.2–7.4 (m, 8H, –C6H4), 6.8–7.9 (m, 4H, –C6H4
of COC6H5NO2)
3.6 (s, 6H, –CH2), 7.2–7.5 (m, 10H, –C6H5), 6.9–7.1 (m, 4H, –C6H4
of COC6H5NO2)
81.0, s
82.1, s
84.1, s
83.1, s
81.0, s
83.9, s
83.9, s
82.9, s
83.0, s
83.9, s
84.1, s
88.6, s
87.1, s
88.2, s
87.9, s
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
Where s = singlet and m = multiplet.
compounds. The 31P chemical shift values of these compounds are given
in Table III.
The 13C NMR spectra of these compounds did not show any ap-
preciable deviation in the chemical shift value of the carbon nu-
clei compared to the parent moieties. The chemical shift for methyl
(–CH3) and methylene (–CH2) carbon occurred in the range δ 22.0–22.9
and δ 42.9–43.2 ppm, respectively. The carbon nuclei of the phenyl
groups (–C6H5 and –C6H4) have displayed their resonance in the

Derivatives of Dibenzyldithiophosphates
2147
region δ 112.1–131.2 ppm. The chemical shift for C–O carbon in meta-
and para-ditolyldithiophosphato derivatives (2–3, 6–7, 10–11, and 14–
15) was found in the region δ 152.1–154.9 ppm, which is indicative of
intramolecular hydrogen bonding between a proton attached to one
of the ortho-carbons of one tolyl ring with an oxygen atom (O–C)
of the other tolyl ring. However, the shift for C–O carbon in ortho-
ditolyldithiophosphato derivatives (1, 5, 9, and 13) was found with an
upfield shift in the range of δ 145.6–146.8 ppm, which shows the absence
of intramolecular hydrogen bonding in ortho-derivatives. The presence
of hydrogen bonding in the compounds (2–3, 6–7, 10–11, and 14–15) is
also supported by the chemical shift for the C–(CH3) carbon in the range
δ 115.2–116.9 ppm compared to the chemical shift in the compounds (1,
5, 9, and 13), which lies in the normal region δ 122.6–122.9 ppm. This
upfield swing for the chemical shift of C–(CH3) carbon in the meta- and
para- derivatives is possible because of hydrogen bonding between the
proton attached to ortho-carbon of one tolyl ring with oxygen atom of
other tolyl ring. In the 13C NMR spectra of the compounds (1–16), four
signals for the phenyl carbons of the organic moiety have been observed
in the region δ 115.1–153.1 ppm for Ci(ip so), Co(ortho), Cm(meta), and Cp(para)
,
respectively. The corrected chemical shift values, δꢀ (δꢀ = Cpara− Cmeta),
are found to be positive in the range 22.6–30.0 for these compounds.37
These positive δꢀ values do not appear in cases like metal dithiophos-
phates, for which δꢀ values are negative since the mode of attachment
of the dithio ligand is referred to as bidentate. These positive values
are suggestive of less polarity of carbon–sulfur bond compared to well
established M–S linkages. The chemical shift of carbonyl carbon C(O)
of organic moiety in the compounds (13–16) occurred in the region δ
190.2–192.4 ppm. The 13C NMR spectral data of these compounds are
summarized in Table IV.
EXPERIMENTAL
General Procedure and Reagents
Benzene and toluene were freshly dried by refluxing over sodium metal
and kept under a nitrogen atmosphere. Moisture was carefully ex-
cluded throughout the experimental manipulations by using standard
Schlenk techniques. Elemental analyses (C, H, N, and S) were per-
formed on a Vario EL III and CHNS-932 Leco elemental analyzer. O,Oꢀ-
Ditolyl/dibenzyldithiophosphate ligands were prepared by a method in
the literature.27 Molecular weights were determined cryoscopically in
freezing benzene. IR spectra were recorded either as nujol mulls or neat
in the range of 4000–400 cm−1 on Perkin Elmer-577 and Shimadzu

2148

Derivatives of Dibenzyldithiophosphates
2149
1
8201 PC spectrophotometers. The H, 13C, and 31P NMR spectra were
recorded on Bruker DRX 300 (300 MHz) and Bruker Avance 400 (400
1
MHz) spectrometer using TMS as an external reference for H NMR
and 85% H3PO4 as an external reference for 31P NMR.
Synthesis of S-(3-Aminophenyl)-O,O’-di(2-
tolyl)phosphorodithioate) [(o-CH3C6H4O)2PS2-m-C6H4NH2] (1)
For the synthesis of (o-CH3C6H4O)2PS2C6H4NH2(1), an approximately
20 cm3 toluene solution of m-chloroaniline, m−ClC6H4NH2(0.38 g, 3.0
mmol) was added dropwise with constant stirring into a toluene suspen-
sion (∼30 cm3) of sodium salt of O,Oꢀ-(o-ditolyl)dithiophosphoric acid,
(o-CH3C6H4O)2PS2Na (1.00 g, 3.0 mmol) in a 100 cm3 round-bottomed
flask. The reaction mixture was refluxed for ∼9 h and then was brought
to room temperature. The precipitated sodium chloride was removed by
filtration using a funnel fitted with a G-4 sintered disc. Subsequently,
excess solvent from the filtrate was evaporated under reduced pressure.
Final drying of the product in vacuo for ∼3 h resulted the compound
(o-CH3C6H4O)2PS2C6H4NH2(1) as light yellow viscous liquid in 94%
yield.
Similar methodology and stoichiometry was used for the synthesis of
all other compounds (2–16). The synthetic and analytical data of these
compounds are given in Table I.
STRUCTURAL FEATURES
It is not possible to predict the precise structure of these compounds,
since we could not produce a single crystal, owing to viscous nature
of the products. However, on the basis of analytical studies such as
elemental analyses, molecular weight determination, IR, and multin-
uclear NMR (1H, 31P, and 13C), a probable geometry may be assigned
to these compounds. It is interesting to note that 31P NMR spectra of
the compounds have shown an upfield shift in the range δ 20–25 ppm
compared to the parent dithio ligands, and this might be due to mon-
odentate behavior of the ligand, since it is found that a low-field shift
(high ppm) is usually observed in the cases when dithiophosphate lig-
and is bonded in bidentate manner.13–19 Hence only one sulfur atom
of the ditotyl/dibenzyl dithiophosphate ligand is attached to the car-
bon atom of organic moiety, leaving another sulfur atom non-bonded.
In conjunction with the reports in the literature,34–36 P−S−C link-
age may be assigned in these compounds in which the phosphorus(V)
atom might have a tetrahedral arrangement such as [(o-, m-, and

2150
S. Sharma et al.
FIGURE 1
p-CH3C6H4O)2PS2-p-C6H4NH2] (Figure 1a) and [(o-, m-, and p-
CH3C6H4O)2PS2-p-COC6H4NO2] (Figure 1b).
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Derivatives of Dibenzyldithiophosphates
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