Synthesis of new tin(IV) compounds of substituted diphenylsulfide derivatives and their complexes with some neutral ligands

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SYNTHESIS OF NEW TIN(IV) COMPOUNDS OF
SUBSTITUTED DIPHENYLSULFIDE DERIVATIVES AND
THEIR COMPLEXES WITH SOME NEUTRAL LIGANDS
Nabeel H. Buttrus a , Mohammed M. Suliman a & Talal A. K. Al-Allaf b
a Department of Chemistry , College of Science, University of Mosul , Mosul, Iraq
b Department of Chemistry , College of Science, Applied Science University , Amman, 11931,
Jordan
Published online: 15 Feb 2007.
To cite this article: Nabeel H. Buttrus , Mohammed M. Suliman & Talal A. K. Al-Allaf (2001) SYNTHESIS OF NEW TIN(IV)
COMPOUNDS OF SUBSTITUTED DIPHENYLSULFIDE DERIVATIVES AND THEIR COMPLEXES WITH SOME NEUTRAL LIGANDS, Synthesis
and Reactivity in Inorganic and Metal-Organic Chemistry, 31:5, 837-848, DOI: 10.1081/SIM-100104854
To link to this article: http://dx.doi.org/10.1081/SIM-100104854
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SYNTH. REACT. INORG. MET.-ORG. CHEM., 31(5), 837–848 (2001)
SYNTHESIS OF NEW TIN(IV)
COMPOUNDS OF SUBSTITUTED
DIPHENYLSULFIDE DERIVATIVES AND
THEIR COMPLEXES WITH SOME
NEUTRAL LIGANDS
Nabeel H. Buttrus,a Mohammed M. Suliman,a and
Talal A. K. Al-Allafa,*
aDepartment of Chemistry, College of Science,
University of Mosul, Mosul, Iraq
ABSTRACT
Some new tin(IV) compounds of the general formula
Sn(SC6H4R)4, where R ¼ o-NH2, p-Me, p-Bu-t have been
obtainedfrom the direct reaction of (RC 6H5S)2 andtin metal
in the molar ratio 2:1 in refluxing toluene. Similarly, a mixture
of tin (RC6H5S)2 andiodine in 1.0:1.5:0.5 or 1.0:1.0:1.0 molar
ratios in refluxing toluene leads to the formation of
Sn(SC6H4R)3I or Sn(SC6H4R)2I2, respectively. Complexes of
the new tin compounds with0 triphenylphosphine, 4-picoline,
1,10-phenanthroline and2,2 -bipyridine have been synthe-
sizedby the direct reaction between the tin compoundandthe
*Current address: Department of Chemistry, College of Science, Applied Science
University, Amman-11931, Jordan. E-mail: talal_al_allaf@hotmail.com
837
Copyright # 2001 by Marcel Dekker, Inc.
www.dekker.com

838
BUTTRUS, SULIMAN, AND AL-ALLAF
neutral ligand. The tin compounds and their adducts have
been characterizedphysio-chemically andspectroscopically.
INTRODUCTION
Compounds of both main group and transition metals with sulfur
donor ligands are a subject of current interest. Substituted disulfide deri-
vatives of main group metals have receivedmuch less attention than those
of the corresponding transition metals. The chemistry of Sn(SR)4,
RxSn(SR0)4-x, tin(II) thiolate and of the corresponding lead compounds
have been reviewed1–4. For indium, In(SC6H5)3 has been preparedeither
by metathesis of InCl3 andNa(SC 6H5)5 or, more simply, by a direct
thermal reaction between indium or tin metal with (C6H5E)2 (E ¼ S, Se) in
refluxing toluene to give the neutral compounds In(EC6H5)3 or Sn(EC6H5)4,
respectively6. The synthesis of dihalobis(2-pyridinethiolato)tin(IV) by an
oxidative-addition reaction of di-2-pyridyldisulfide to tin(II) halides repre-
sents an example of preparing other similar dihalodithiolatotin(IV) com-
pounds7. In our recent article, we have describe the direct reaction between
bismuth metal with (o-H2NC6H4S)2 and( p-MeC6H4S)2 in refluxing toluene
to give the corresponding bismuth compounds Bi(SC6H4NH2-o)3 and
Bi(SC6H4Me-p)3, respectively8.
In the present work, the oxidative addition of the -S-S- linkage of
(RC6H4S)2, R ¼ o-NH2, p-Me, p-Bu-t to tin metal alone andto tin metal in
the presence of iodine in different molar ratios are discussed. Also reported
is the synthesis of complexes of the new tin(IV) compounds with some
neutral donor ligands, i.e., triphenylphosphine (PPh3), 4-picoline (4-pic),
0
1,10-phenanthroline (phen) and2,2 -bipyridine (bipy), as a part of our
continuedinterest in investigating this type of interaction between tin metal
and various donor ligands9–12
.
EXPERIMENTAL
Measurements
IR spectra were recorded on a Perkin-Elmer 580 infrared spectro-
photometer over the range 200–4000 cmÀ1 using CsI pellets. Analyses of the
compounds were carried out with a type 1106 (Carlo Erba) CHN analyser.
UV-Vis. spectra were recorded on a UV 1160 Shimadzu UV-Vis. recording
spectrophotometer. Conductivity measurements were obtained in 10À3 M,

SYNTHESIS OF NEW TIN(IV) COMPOUNDS
839
solutions of the compounds in DMF at room temperature (25 ꢀC), using a
model 4070 Jenway conductivity meter.
Starting Materials
Tin metal, toluene andsubstitutedthiols were commercial products
(Fluka) and used as supplied. The disulfides, (RC6H4S)2, R ¼ o-NH2, p-Me,
p-Bu-t, were synthesized by standard methods13.
Preparation of Tin(IV) Compounds
Sn(SC6H4R)4. A mixture of finely cut tin metal (0.12 g, 1.0 mmol)
and the disulfide (RC6H4S)2 (2.0 mmol) in toluene (30 mL) was refluxedfor
4 h. The reaction mixture was filteredthrough Celite andthe resultant
yellow solution was reduced to ca. 10 mL by evaporation under reduced
pressure. The solidthus obtaine,d after cooling in an ice-bath, was
collectedby filtration, washedwith petroleum ether (60–80 ꢀC) anddried
in vacuo.
Sn(SC6H4R)3I. Finely cut tin metal (0.12 g, 1.0 mmol) was refluxed
with the disulfide (RC6H4S)2 (1.5 mmol) andiodine (0.064 g, 0.50 mmol) in
toluene (30 mL) for 4 h. The reaction mixture was filteredthrough Celite and
the resultant yellow or brown solution was reduced to ca. 10 mL by eva-
poration under reduced pressure. The solid thus obtained, after cooling
in an ice-bath, was collectedby filtration, washedwith petroleum ether
(60–80 ꢀC) anddried in vacuo.
Sn(SC6H4R)2I2. These compounds were prepared in a manner
similar to the Sn(SC6H4R)3I compounds, except that equimolar quantities
of both tin, disulfide and iodine (1.0 mmol) were used.
0
Preparation of Sn(SC6H4R)4Á2L orL Complexes
.
Sn(SC6H4NH2-o)4 2PPh3. The tin compoundSn(SC 6H4NH2-o)4
(0.54 g, 1.0 mmol) was added to a solution of the ligand PPh3 (0.52 g,
2.0 mmol) in n-pentane (20 mL) at room temperature. The reaction mixture
was stirred for 4 h, during which time a precipitate formed. It was collected
by filtration, washedwith n-pentane anddried in vacuo.

840
BUTTRUS, SULIMAN, AND AL-ALLAF
Sn(SC6H4NH2-o)4 2(4-pic). The tin compoundSn(SC 6H4NH2-o)4
.
(0.54 g, 1.0 mmol) and4-picoline (0.186 g, 2.0 mmol) was mixedin methanol
(15 mL) to yielda green oil, which became a solidon stirring for ca. 4 h. The
solidwas then collectedby filtration, washed3 times with 5 mL of methanol
anddried in vacuo.
.
Sn(SC6H4NH2-o)4 phen. The tin compoundSn(SC 6H4NH2-o)4
(0.54 g, 1.0 mmol) was stirredwith 1,10-phenanthroline (0.18 g, 1.0 mmol) in
methanol (10 mL) for ca. 4 h, during which time a red-orange oil formed,
which became a solidupon stirring for further 2 h. The solidwas filteredoff,
washed3 times with 5 mL of methanol anddried in vacuo.
0
.
Sn(SC6H4NH2-o)4 bip. The tin compoundSn(SC 6H4NH2 -o)4
0
(0.54 g, 1.0 mmol) was stirredwith 2,2 -bipyridine (0.16 g, 1.0 mmol) in ben-
zene (20 mL) for ca. 2 h, during which time a yellow oily layer was separated
from the colourless solution, and the colourless layer was decanted. The oil
was triturated with diethyl ether (30 mL) until it solidified and the resultant
yellow solidwas filtered, washedwith ether anddried
The analogous complexes with R ¼ p-Me and p-Bu-t were prepared
similarly.
in vacuo.
RESULTS AND DISCUSSION
The methoddescribedin this work clearly represents a simple and
efficient one-pot synthesis of a number of Sn(SC6H4R)4 compounds, where
R is o-NH2, p-Me or p-Bu-t, by a direct oxidative addition reaction of the
disulfides to tin metal. These reactions are noticeably simpler than those
usedin the past for the preparation of M(SPh) compounds of main group
n
elements, involving metathesis reactions of MCln with Na(SPh), Li(SPh) or
Mg(SPh})25,14. Also, the thermal reactions are clearly different from those
involving the electrochemical oxidation of metal anodes in non-aqueous
media, since the latter method is known to give benzenthiolates of zinc, tin
15,16
andthallium
.
The most likely primary reaction is that shown in eq (1), giving a 1þ or
2þ oxidation state species. In the case of bismuth, indium and tin, this
wouldbe followedby the reaction of eq (2).
2M þ ðRSÞ À! 2MðSRÞ
ð1Þ
ð2Þ
2MðSRÞ þ 2ðn À 1ÞðRSÞ2 À! 2MðSRÞn
ðM ¼ Bi or In; n ¼ 3 and M ¼ Sn; n ¼ 4Þ

SYNTHESIS OF NEW TIN(IV) COMPOUNDS
841
The oxidative insertion process of eq (2) is clearly analogous to the
known reactions involving the conversions7,8
:
In0 À! In3þ or Sn2þ À! Sn4þ
The analytical data of the tin compounds Sn(SC6H4R)4 (R ¼ o-NH2,
p-Me, p-Bu-t) and their adducts with the neutral ligands 2L and L0 are given
in Table I. These data are in good agreement with the proposed formulas.
All of the compounds are air-stable at room temperature and insoluble in
the common organic solvents. They are, however, soluble in dimethylfor-
mamide (DMF) and other donor solvents.
The most important diagnostic features of the IR spectra are listed
in Table II. The IR bands of the free disulfide species are included here
for comparison. At a quick glance at Table II, one can see that a drastic
decrease in the n(NH2) frequency of the free disulfide (o-NH2C6H4S)2
from 3395 to ca. 3260 cmÀ1 upon forming Sn(SC6H4NH2-o)xI4-x
,
x ¼ 4,3,2, i.e., compounds (1), (4) and (7), respectively. This may well be
attributedto intramolecular coordination between the NH group andSn,
2
in which two NH2 groups are bonded to metal through the nitrogen
atoms17, in addition to four sulfur atoms forming an octahedral geometry
aroundthe tin atom. It seems likely that this coordination is only temporary
in these compounds because when reacted with the neutral ligands 2L or L0,
the former coordination with NH2 is displaced by the stronger inter-
molecular coordination with P or N atoms of the neutral ligands (vide infra).
À1
The frequency of the (C-S) bandobservedat 1000–1040 cm
for the free
disulfides is only slightly increased upon forming the corresponding
tin compounds (Table II), which indicates that the tin compounds
Sn(SC6H4NH2-o)xI4-x had formed. Further support for this is provided by
À1
the appearance of new bands at about 323–342 cmÀ1 and400–440 cm
which are tentatively attributedto (Sn-S) and(Sn-N), respectively. Fur-
thermore, the IR spectra of the complexes Sn(SC6H4R)Á2L or L0, i.e.,
complexes (10)–(21) (Table I andII) show a clear strong bandat
ca.
3385 cmÀ1, which is assignedto uncoordinated(NH 2) while the (C-S) band
À1
which is observedat 1018–1060 cm indicates that the S atom is still
bonded to Sn and no drastic change was observed on going from the tin
À1
compoundto its complex. Similarly, the IR bandat 323–336 cm
in the
complexes (10)–(21) is assignedto (Sn-S) while the (Sn-N) absorptions are
dependent on the free ligand used. The (Sn-N) band at 264–300 cmÀ1 is due
to phen andbipy ligansd [complexes ( 16)–(21)] andthis is in a good
agreement with the reportedvalues for InX 3.1.5phen (X ¼ Cl, Br)18,19
which fall in the range 220–290 cmÀ1. With the ligand4-pic, the (Sn-N) band
was observedat 429–446 cm À1 [complexes (11), (13) and( 15)] andthe (Sn-P)
À1
bandfor complexes ( 10), (12) and( 14) was observedat 488–514 cm

Table I. Physical Properties andAnalyses of Sn(SC 6H4R)xI4-X (x ¼ 4, 3,2) Compounds and Sn(SC6H4R)4 Á 2L or L0 Complexesa
Analysis: Found(Calcd.)%
M.p.
ꢀC)
Empirical
Formula
Formula Yield
Weight (%)
Cond.b
Seq.
CompoundColor
(
C
H
N
LM
(1) Sn(SC6H4NH2-o)4
yellow 106–108 C24H24N4S4Sn
yellow 86–88 C28H28S4Sn
614.6 97 47.02 (46.85) 4.10 (3.90) 8.88 (9.11) 32
(2) Sn(SC6H4Me-p)4
(3) Sn(SC6H4But-p)4
(4) Sn(SC6H4NH2-o)3I
610.7 83 55.12 (55.02) 4.71 (4.58)
778.7 96 61.14 (61.14) 6.62 (6.67)
15
23
yellow 100–102 C40H52S4Sn
golden 185–187 C18H18N3S3ISn
yellow
617.7 98 35.11 (34.97) 3.09 (2.91) 6.55 (6.80) 63
(5) Sn(SC6H4Me-p)3I
(6) Sn(SC6H4But-p)3I
(7) Sn(SC6H4NH2-o)2I2
(8) Sn(SC6H4Me-p)2I2
(9) Sn(SC6H4But-p)2I2
yellow 300c
C21H21S3ISn
yellow >300 C30H39S3ISn
614.7 73 40.87 (41.00) 3.51 (3.42)
740.7 60 48.54 (48.60) 5.19 (5.26)
59
67
brown 193–196 C12H12N2S2I2Sn 620.7 82 22.89 (23.20) 2.08 (1.93) 4.29 (4.51) 90
orange 124–126 C14H14S2I2Sn
orange >360 C20H26S2I2Sn
618.7 69 27.10 (27.15) 2.28 (2.26)
702.7 65 34.20 (34.15) 3.65 (3.70)
101
112
(10) Sn(SC6H4NH2-o)4 Á 2PPh3 yellow
(11) Sn(SC6H4NH2-o)4 Á 2(4-Pic) yellow
(12) Sn(SC6H4Me-p)4 Á 2PPh3 pale
66–68 C60H54N4S4P2Sn 1138.7 86 63.13 (63.23) 4.80 (4.74) 4.87 (4.92) 16
800.7 65 52.95 (5395) 4.54 (4.75) 10.39 (10.49) 20
1134.7 96 66.81 (67.68) 5.09 (5.11) 17
94–95 C36H38N6S4Sn
76–78 C64H58P2S4Sn
yellow
(13) Sn(SC6H4Me-p)4 Á 2(4-Pic) yellow
(14) Sn(SC6H4But-p)4 Á 2PPh3 pale
90–92 C40H42N2S4Sn
60–62 C76H82P2S4Sn
796.7 80 60.17 (60.02) 5.19 (5.27) 3.62 (3.51) 18
1302.7 92 70.08 (70.00) 6.38 (6.29) 10
yellow
(15) Sn(SC6H4But-p)4 Á 2(4-Pic) pale
90–92 C52H66N2S4Sn
964.7 82 64.65 (64.68) 6.82 (6.29) 2.92 (2.90) 24
yellow

(16) Sn(SC6H4NH2-o)4 Á phen orange 100–102 C36H32N6S4Sn
794.7 89 53.99 (54.36) 4.10 (4.03) 10.51 (10.57) 22
770.7 78 53.54 (52.94) 4.22 (4.15) 10.66 (10.90) 25
red
(17) Sn(SC6H4NH2-o)4 Á bipy
pale
yellow
lemon 152–154 C40H36N2S4Sn
orange 98–100 C38H36N2S4Sn
lemon 198–200 C52H60N2S4Sn
lemon 112–115 C50H60N2S4Sn
113–114 C34H32N6S4Sn
(18) Sn(SC6H4Me-p)4 Á phen
(19) Sn(SC6H4Me-p)4 Á bipy
(20) Sn(SC6H4But-p)4 Á phen
(21) Sn(SC6H4But-p)4 Á bipy
790.7 90 60.39 (60.71) 4.69 (4.55)
16
766.7 98 60.04 (59.48) 4.82 (4.70) 3.62 (3.65) 14
958.7 93 64.99 (65.09) 6.29 (6.26) 2.85 (2.92) 10
934.7 75 64.09 (64.19) 6.39 (6.42) 2.98 (3.00) 19
a
0
For R, L andL , see Fig. 1.
bConductivity measured in DMF (ohmÀ1 molÀ1 cm2).
cCompoundmelts with decomposition.

Table II. IR Absorptions and Electronic Spectral Data for the Disulfides, Tin(IV) Compounds, and Their Complexes
À1 b
U.V.=Vis. Bands
lmax (nm)
SelectedIR Bands (cm
)
Compounda
Seq.
n(NH2)
n(C-S)
n(Sn-S)
n(Sn-N)
n(Sn-P)
(emax (dm3 molÀ1 cmÀ1))
c
(o-NH2C6H4S)2
c
( p-MeC6H4S)2
3395 s
1040 s
1015 s
1000 s
1058 s
284 (12100), 348 (23400)
250 (6500), 294 (23930)
247 (5610), 298 (24920)
280 (24700), 308 (16800),
383 (13780)
c
( p-ButC6H4S)2
(1)
3264 w
323 m
441 s
(2)
(3)
(4)
(5)
(6)
(7)
(8)
(9)
1027 s
1112 s
1060 s
1032 s
1115 s
1069 s
1033 m
1020 s
1055 s
1060 s
342 s
333 s
268 (25480), 310 (18720)
265 (21420), 348 (9130)
254 (13710), 344 (2085)
270 (25400), 325 (21280)
244 (7810), 298 (23780)
281 (21900), 378 (22980)
283 (24930), 339 (24860)
252 (8230), 378 (16720)
290 (22810), 381 (25730)
283 (24940), 346 (15680),
371 (18250)
d
3260 m
3216 w
329 w
329 w
336 w
340 w
336 w
340 m
323 m
325 m
399 w
(10)
(11)
3388 s
3378 s
514 w
446 b
(12)
(13)
(14)
1028 m
1033 s
1020 s
308 w
315 w
335 m
492 s
488 b
281 (22370), 387 (19870)
268 (23180), 344 (11270)
270 (14820), 318 (24910),
365 (20900)
443 m
(15)
(16)
1018 s
1050 s
336 w
326 m
429 m
264 w
267 (14500), 299 (21730),
356 (12310)
289 (24940), 381 (16780)
3387 s

(17)
3390 s
1054 s
326 m
463 w
285 (23890), 361 (17520),
381 (21730)
(18)
(19)
1027 m
1032 s
329 w
335 m
288 w
265 sh
283 (25400), 376 (16970)
270 (24910), 313 (16840),
361 (10190)
(20)
1018 s
326 w
333 w
275 w
300 w
273 (24170), 303 (12340),
346 (7630)
263 (21300), 371 (13860)
(21)
1018 s
aFor the compounds (1)–(21), see Fig. 1 and Table I.
bFor IR data: s, strong; m, medium; w, weak; b, broad; sh, shoulder bands.
cData for disulfides included here for comparisons.
dBandnot observed.

846
BUTTRUS, SULIMAN, AND AL-ALLAF
X ¼ Y ¼ Z ¼ SC6H4-R X ¼ SC6H4R; R ¼ o-NH2 X ¼ SC6H4R; R ¼ o-NH2
(1) R ¼ o-NH2
(2) R ¼ p-Me
(3) R ¼ p-Bu-t
(10) L ¼ PPh3
(11) L ¼ 4-pic
R ¼ p-Me
(16) L0 ¼ phen
(17) L0 ¼ bipy
R ¼ p-Me
Y ¼ I, X ¼ Z ¼ SC6H4R (12) L ¼ PPh3
(18) L0 ¼ phen
(4) R ¼ o-NH2
(5) R ¼ p-Me
(6) R ¼ p-Bu-t
(13) L ¼ 4-pic
R ¼ p-Bu-t
(19) L0bipy
R ¼ p-Bu-t
(14) L ¼ PPh3
(20) L0 ¼ phen
Y ¼ Z ¼ I, X ¼ SC6H4R (15) L ¼ 4-pic
(7) R ¼ o-NH2
(21) L0 ¼ bipy
(8) R ¼ p-Me
(9) R ¼ p-Bu-t
Figure 1. The suggestedstructures for the tin(IV) compounds andtheir complexes
with neutral ligands. For the expected structures of compounds (1), (4) and (7),
see text.
(Table II); similar observations were reportedby Roundhill 20. It is con-
cluded that the tin complexes Sn(SC6H4-R)4 Á 2L or L0 obtainedin this study
might well have octahedral structures (Fig. 1), probably with some distor-
tion. A similar study of complexes such as Sn(SC6H5)4 Á bipy by X-ray single
crystal diffraction showed it to have a distorted octahedral SnS4N2 unit5.
The UV=Vis. spectra of the tin compounds and their complexes are
similar to one another but different from those of the free disulfides
(Table II). The broad bands observed in the range 247–348 nm are due
to p ! p* or n ! p* transitions of the free disulfides, while a new addi-
tional bandwas observedfor almost all tin compounds andtheir com-
plexes in the range 356–387 nm. This bandmay be attributedto the
charge transfer from filledligandorbitals to the vacant metal orbitals.
The molar conductivities of 10À3 M solutions of the tin compounds
andtheir complexes (Table I) indicate that they are non-electrolytes in
DMF21, except for the compounds (4)–(6) which are 1:1 electrolytes and
compounds (7)–(9) which are 1:2 electrolytes. This could be due to dis-
placement of iodide ion=ions in the compounds by DMF22,23
.

SYNTHESIS OF NEW TIN(IV) COMPOUNDS
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Received: April 28, 2000
Accepted: March 15, 2001
Referee I: D. G. Tuck
Referee II: J. Iriarte-Gross