New organotin(IV) chlorides derived from N-(2-hydroxyphenyl)aryloxy sulfamates. Synthesis, characterization and DSC investigation

Article abstract of DOI:10.1007/s12039-018-1586-1

Abstract: Three monomeric pentacoordinate organotin complexes were prepared by the reaction of dimethyltin dichloride with three N-(2-hydroxy)phenyl substituted aryloxy sulfamates in alkaline medium. The newly synthesized compounds were characterized on the basis of their infrared, CPMAS NMR, powder XRD diffraction and elemental analysis. The XRD powder analyses revealed a tetragonal system for two complexes, whereas the third one was crystallized in the hexagonal system. The thermal decomposition behavior of the synthesized complexes have been investigated and all the organotin compounds have a similar order of thermal stability. Graphical Abstract : Synopsis We synthesized three organotin complexes 3a-c and have investigated their thermal properties. The XRD powder analyses revealed tetragonal system for two complexes, whereas the third one crystallized in hexagonal system. The differential scanning calorimetric data demonstrate high stability of all the synthesized complexes.[Figure not available: see fulltext.].

Full text of DOI:10.1007/s12039-018-1586-1

J. Chem. Sci.
(2019) 131:12
© Indian Academy of Sciences
https://doi.org/10.1007/s12039-018-1586-1
REGULAR ARTICLE
New organotin(IV) chlorides derived from
N-(2-hydroxyphenyl)aryloxy sulfamates. Synthesis,
characterization and DSC investigation
ALI AKREMIa,b,∗ and ADEL NOUBIGHa,c
aDepartment of Chemistry, Faculty of Science, Northern Border University, Arar 91431,
Kingdom of Saudi Arabia
bDepartment of Chemistry, High Institute of Environmental Sciences and Technologies, Carthage University,
Borj Cedria, Tunisia
cLaboratory of Physical Chemistry of Materials, Preparatory Institute for Scientific and Technical Studies of La
Marsa, 2070, Carthage University, Tunis, Tunisia
E-mail: akrimimi@gmail.com
MS received 4 September 2018; revised 17 December 2018; accepted 17 December 2018
Abstract. Threemonomericpentacoordinateorganotincomplexeswerepreparedbythereactionofdimethyltin
dichloride with three N-(2-hydroxy)phenyl substituted aryloxy sulfamates in alkaline medium. The newly
synthesizedcompoundswerecharacterizedonthebasisoftheirinfrared, CPMASNMR, powderXRDdiffraction
and elemental analysis. The XRD powder analyses revealed a tetragonal system for two complexes, whereas
the third one was crystallized in the hexagonal system. The thermal decomposition behavior of the synthesized
complexes have been investigated and all the organotin compounds have a similar order of thermal stability.
Keywords. Penta-coordinate complex; organotin complexes; sulfamates; powder XRD; thermal stability .
1. Introduction
(−SO2NH−CO) groups to transition metals has been
rarely investigated especially for the purpose of
developing new organometallic sulfamate deri-
vatives and exploring their presumed biological
activities.33–35
Sulfamates are found to be suitable intermediates
for the design and development of various types of
new molecules as therapeutic agents and for bio-
logical or pharmaceutical uses. Sulfamate derivatives
have been identified as bioactive molecules which
occupy a prominent place in medicinal chemistry
because of their wide range therapeutic properties,
such as anti-cancer,1–5 antibacterial,6–10 antioxidant,11,12
anti-HIV,13–15 anticonvulsant,16–19 antibiotic,13,20,21 anti-
obesity,22 diuretic,23,24 hypoglycemic,25 antithyroid,26
and anti-neuropathic pain27 activities. In addition, the
electronic structure of −SO2NH2 group in sulfamates
and related ligands was considered as moiety par
excellence for designing potent carbonic anhydrases
inhibitors (CAIs) because of its good chelating to
the metal ion of the enzyme.28–32 Thus, complexa-
tion reaction of sulfonyl (−SO2NH2) and N-sulfamoyl
On the other hand, organotin complexes have been
found to be encouraging agents for stimulating anti-
cancer activity, many of them are as effective or
even better than traditional drugs.36–39 In our previ-
ous work, we have reported the synthesis of some new
Sn(IV) complexes with 2-alkylaminobenzimidazole lig-
ands.40 In the current work, we describe synthesis,
characterization and thermal studies of dimethyltin
dichloride adduct with N-(2-hydroxyphenyl) substi-
tuted aryloxy sulfamates. The molecular structure of the
opted multi-dentate sulfamate might affect the planarity,
hydrophobicity, and coordination geometry of tin com-
plexes and perhaps the anticancer activity of tin-based
agents.
*
For correspondence
Electronic supplementary material: The online version of this article (https://doi.org/10.1007/s12039-018-1586-1) contains
supplementary material, which is available to authorized users.
0123456789().: V,-vol

12 Page 2 of 8
J. Chem. Sci.
(2019) 131:12
νNH
ν
ν
ν
2. Experimental
3370, CHarom 3080, C=O 1690, 1612, 1502,
C=Carom
1448, SO2 1373. 1H NMR (δ, ppm in CDCl3) : 7.8−6.8 (m;
Harom, 8H), 6.5 (br, NH, 1H), 3.9 (s, OH; 1H). 13C NMR (δ,
ppm in CDCl3): δ168.5, 164.1, 161.1, 145.2, 134.1, 129.5,
121.0, 119.9, 118.0, 117.6, 115.4. Anal. Calculated(%) for
C13H10FNO5S: C, 50.15; H, 3.23; N, 4.49. Found(%): C,
50.14; H, 3.20; N, 4.47.
ν
2.1 Materials and methods
The melting point of the complexes was recorded by a
differential scanning calorimetric instrument (DSC 131 evo-
Setaram, France). The IR spectra were measured using a
Nicolet iS5 Infrared Spectrometer in KBr disc (Thermo
Scientific, USA). 1H NMR, 13C NMR and 119Sn spectra
were recorded by Bruker Avance 300 spectrometer (Bruker,
France) at 300 and 75 MHz, respectively. Chemical shifts
2.3 Synthesis of organotin complexes 3a–c
The alcoholic solution of 1 mmol of dimethyltin dichloride
was added with constant stirring to an alcoholic solution of
1mmolofSodiumsaltofsubstitutedaryloxysulfamateligand.
The brown precipitates were instantly obtained. The precip-
itates were filtered and washed with water and then with
Methanol and dried over calcium chloride in a desiccator.
were reported in ppm from internal TMS for H, 13C and
1
119Sn. Elemental analysis was obtained by an Exeter Analyt-
ical CE-440 Elemental instrument (Exeter Analytical, UK).
X-ray spectra were recorded by an Oxford X-calibur Gemini
diffractometer (Santa Clara, California, USA) equipped with
EOS CCD detector using monochromated Mo Ka radiation
(k = 0.71073 Å) at room temperature. All reagents and sol-
vents used in this study were commercially available (from
Sigma-Aldrich) and were used without further purification.
The intermediate compounds were prepared according to the
literature methods.
2.3.1 [Me2Sn(L1)Cl](3a): Brown solid. Yield: 54%. M.p.:
373 ◦C. IR (cm−1): OH 3440; C=N 1608 and 1522;
ν
ν
ν
Sn−C
578; Sn−N 507. 13C CPMAS NMR (ppm): 183–164(C=O
andC=N); 137–117(Carom); 80−40(CH3arom), 14−8(CH3
-Sn). Anal. Calculated(%) for C18H22ClNO5SSn: C, 41.69;
H, 4.28; N, 2.70. Found(%): C, 41.67; H, 4.25; N, 2.69.
ν
2.2 Synthesis of substituted phenyloxy (2-hydroxyben
zoyl)sulfamates 2a–c
2.3.2 [Me2Sn(L2)Cl](3b): Brown solid. Yield: in 41%.
M.p.: 338 ◦C. IR data (cm−1): OH 3452;
1610 and
ν
ν
C=N
Freshly prepared and distilled aryloxysulfonyl isocyanate (1
equiv.) and salicylic acid (1 equiv.) were taken in a round
bottom flask and anhyd. toluene (10 mL) was added to it
followed trimethylamine (0.05 equiv.). Then it was stirred
in an argon atmosphere at room temperature. The reaction
was monitored by TLC and was found to be completed after
30 min. The crude solid was filtered and recrystallized from
carbon tetrachloride.
νSn−C
ν
1526;
571; Sn−N 510. 13C CPMAS NMR (ppm):
182 − 164(C=O and C=N); 138 − 116(Carom); 14 − 8(CH3
-Sn). Anal. Calculated(%) for C15H13Cl4NO5SSn: C, 31.07;
H, 2.26; N, 2.42. Found(%): C, 31.05; H, 2.25; N, 2.41.
2.3.3 [Me2Sn(L3)Cl] (3c): Brown solid. Yield: 44%, M.p.:
299 ◦C. IR data (cm−1):
3444;
1606 and 1526;
νOH
ν
C=N
576; Sn−N 511. 13C CPMAS NMR (ppm): 185−165
νSn−C
ν
(C=O and C=N); 144−121(Carom); 13−8(CH3-Sn). Anal.
2.2.1 Mesityl (2-hydroxybenzoyl)sulfamate (2a): White Calculated (%) for C15H15ClFNO5SSn: C, 36.43; H, 3.06;
solid. Yield: 94%. M.p.: 74 ◦C. IR (cm−1): OH 3444,
N, 2.83. Found(%): C, 36.40; H, 3.05; N, 2.80.
ν
ν
NH
ν
ν
ν
3355, CHarom 3076, C=O 1658, C=Carom 1612, 1549, 1475,
1448, SO2 1350. 1H NMR (δ, ppm in CDCl3) : 7.9−6.6(m;
ν
H
arom, 6H), 5.4 (br, NH, 1H), 4.4 (s, OH; 1H), 2.4 − 2.3 (2 s,
3. Results and Discussion
CH3arom; 9H). 13C NMR (δ, ppm in CDCl3): δ167.2, 160.4,
143.4, 134.1, 129.2, 127.7, 119.9, 117.5, 115.2, 21.8, 16.5.
Anal. Calculated(%) for C16H17NO5S: C, 57.30; H, 5.10; N,
4.17; Found(%): C, 57.27; H, 5.09; N, 4.14.
3.1 Chemistry
The synthesis of new sulfamate derivative ligands (LnH)
2a–c has been carried out in a basic medium at room
temperature by the addition of 2-hydroxy benzoic acid
to a series of substituted aryloxy sulfonylisocyanates
1a–c which followed by decarboxylation reaction41
(Scheme 1). The latter isocyanates were prepared
according to literature methods.42,43
2.2.2 2,4,6-Trichlorophenyl (2-hydroxybenzoyl)sulfa
mate (2b): White solid. Yield: 91%. M.p.: 86 ◦C. IR (cm−1):
νOH
ν
νCHarom
νC=O
νC=Carom
3436, NH 3361,
3087,
1682,
1
ν
1614, 1568, 1473, SO2 1378. H NMR (δ, ppm in CDCl3):
7.7 − 7.0 (m; Harom, 6H), 6.2 (br, NH, 1H), 4.1 (s, OH; 1H).
13C NMR (δ, ppm in CDCl3): δ168.2, 161.4, 145.9, 134.3,
130.0, 129.6, 120.1, 117.9, 115.8. Anal. Calculated(%) for
C13H8Cl3NO5S: C, 39.36; H, 2.03; N, 3.53. Found(%): C,
39.33; H, 2.00; N, 3.52.
Dimethylthin phenyloxy (2-hydroxybenzoyl)sulfa
mate complexes 3a–c [Me2Sn(Ln)Cl] were synthe-
sized from N-(2-hydroxyphenoyl) substituted aryloxy
sulfamates 2a–c in alkaline medium, and its metal
complexes were prepared. As a result of the electro-
2.2.34-Fluorophenyl(2-hydroxybenzoyl)sulfamate (2c):
White solid. Yield: 93%. M.p.: 69 ◦C. IR (cm−1): OH 3448, attractor effect of both sulfonyl and carbonyl groups,
ν

J. Chem. Sci.
(2019) 131:12
Page 3 of 8
12
Scheme 1. Synthesis of substituted phenyloxy (2-hydroxybenzoyl)sulfamates 2a–c.
Scheme 2. Synthesis of sulfamate complexes 3a–c.
the proton sulfamate group NH is more acidic than the respectively, due to the hydroxyl (OH) chromophore.
proton hydroxyl group OH; therefore, a significant con- Thus, the absorption bands observed at 3375 cm−1 and
jugated bidentate ligand would be formed and reacted 1656 cm−1 in IR spectrum of 2c which assigned to (N-
with the Tin halide, in 1:1 molar ratio, as shown in H) and (C=O) groups respectively, were disappeared in
Scheme 2.
the homologous IR spectrum of 3c in favor of appear-
The composition of isolated complexes was con- ance of new bands exhibited at (1609, 1514) cm−1 and
firmed by the findings obtained from elemental analyses (565–547) cm−1 which might be attributed to (C=N) and
which performed by an Exeter Analytical CE-440 Ele- (Sn-C) chromophores correspondently (Figure 1). The
mental instrument. It has been found that in all ligands absorption bands of both carbonyl and imino groups are
(LnH) 2a–c, one chloride was substituted by monoan- hardly observed probably because of the high conjuga-
ionic ligands and furnished with moderate yields their tion (Scheme 2).
corresponding mononuclear complexes 3a–c.
The 13C NMR spectra of compounds 3a–c displayed
Upon coordination to tin atom, many absorption one set of resonances which were consistent with the
bands were markedly shifted. The three complexes presence of one organotin(IV) moiety and equivalence
3a–cexhibitedbroadbandsat3440, 3449, and3444cm−1 of the methyl groups attached to tin on the NMR time

12 Page 4 of 8
J. Chem. Sci.
(2019) 131:12
scale (Figure 2). Indeed, the signals observed at 14– and shown in Figure 3. All spectra revealed sharp
8 ppm were assigned to CH3-Sn carbon group, whereas, peaks with significant diffraction intensity and low
the signals exhibited at 80–40 ppm were attributed to the background. Indexing of the powder diffraction pat-
aromatic methyl (CH3arom) carbon group. The aromatic tern and searching space group of the crystal specimen
carbons displayed signals at 137–117 ppm. The C=O were determined using X-pert high score plus soft-
and C=N carbon groups presented signals located at ware program after peak searching (Figure 3). Particular
185–165 ppm.
structural properties and features obtained are presented
X-ray spectra of synthesized complexes 3a–c were in Tables 1–3, respectively. The organotin compounds
recorded by an Oxford X-calibur Gemini diffractometer 3a and 3b show tetragonal crystal system, while, the
crystal structure of complex 3c belong to the hexagonal
system. Crystallite size Dp for all complexes 3a–c have
been calculated using Scherrer formula44 and obtained
values are 142 nm, 76 nm, and 70 nm, respectively.
Kλ
Dp =
β cos θ
Dp is the size of particles of crystals in the form of
powder, K is a dimensionless shape factor with a value
close to unity, λ is the X-ray wavelength, β is the line
broadening at half the maximum intensity (FWHM),
after subtracting the instrumental line broadening, in
radians and θ is the Bragg angle.
Tables 1–3 show that all the diffraction peaks in the
pattern of the synthesized organotin complexes 3a–c can
be readily indexed by a set of lattice parameters. The
Figure 1. Infrared spectra of ligand 2c and its correspond-
ing complex 3c.
relative deviations between the calculated and experi-
mental are about 1.13%, 0.37%, and 0.36% for products
Figure 2. 13C CPMAS NMR spectrum of organotin complex 3a.

J. Chem. Sci.
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Page 5 of 8
12
Figure 3. X-ray patterns of complexes 3a–c and indexation peak using X-pert high score plus software.
Table 1. Experimental data and calculated results for the powder X-ray diffraction pattern of 3a,
tetragonal symmetry.
Peak no. 2 (c) [◦] 2 (o) [◦] d-sp. (c)[Å] d-sp. (o) [Å] Relative intensity (%)
hkl
θ
θ
1
2
3
4
5
6
7
8
11.5707
12.4071
16.3915
23.2616
24.9628
25.3287
27.593
31.6343
35.2044
36.3925
38.2233
43.6406
45.2256
49.3459
52.2106
56.5098
66.0679
75.1509
83.9897
11.4789
12.3876
16.4768
23.131
25.0595
25.3407
27.2856
31.6316
35.134
36.4842
38.0732
43.7133
45.3761
49.3517
52.2846
56.3931
66.1456
75.2085
83.9029
7.641693
7.128348
5.403492
3.820846
3.564174
3.513511
3.23011
2.826082
2.547231
2.466749
2.352707
2.072384
2.003371
1.845302
1.75059
7.702639
7.139563
5.375722
3.842123
3.550645
3.511875
3.2658
2.826311
2.552172
2.460762
2.361631
2.069108
1.997076
1.845099
1.748288
1.63027
12.56
47.90
5.26
100
101
110
200
202
105
212
007
300
302
108
322
218
411
1011
2011
0014
602
5111
2.31
19.92
15.76
16.02
100.00
2.24
2.27
1.46
6.21
58.11
8.75
1.93
13.26
5.67
9
10
11
12
13
14
15
16
17
18
19
1.627179
1.413041
1.263187
1.151308
1.411568
1.262364
1.152279
11.88
6.41
◦
γ
α
Lattice parameters calculated: a = 7.64 Å, b = 7.64 Å, c = 19.78 Å and = β = = 90
Particle size of complex 3a: 142 nm, V = 1155.21 Å3. (2Theta Zero Shift [◦], 0.0(1)).

12 Page 6 of 8
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Table 2. Experimental data and calculated results for the powder X-ray diffraction pattern of 3b,
tetragonal symmetry.
Peak no. 2 (c) [◦] 2 (o) [◦] d-sp. (c) [Å] d-sp. (o) [Å] Relative intensity (%)
hkl
θ
θ
1
2
3
4
5
6
7
8
10.4175
11.9636
16.1204
20.9224
22.259
10.4552
11.9934
16.1441
20.8978
22.3631
24.6695
26.3521
31.7311
32.5138
33.1522
35.0121
36.5498
37.0893
40.1444
42.2347
44.3299
45.482
8.484892
7.391633
5.493742
4.242446
3.990629
3.589231
3.370199
2.828297
2.746871
2.702254
2.566839
2.463877
2.424255
2.240761
2.13062
2.038026
1.99243
1.923011
1.685099
1.62884
1.26064
1.151497
8.454357
7.373334
5.485749
4.247382
3.972279
3.605881
3.379341
2.817677
2.751613
2.700069
2.560783
2.456496
2.421989
2.244435
2.138059
2.041746
1.99267
14.84
100.00
91.50
14.54
53.07
10.22
19.68
45.82
28.86
18.31
13.10
8.53
15.59
10.89
12.02
5.49
16.86
4.77
002
101
111
004
201
211
212
006
222
301
311
303
007
216
305
401
118
331
424
1110
536
635
24.7858
26.4248
31.6088
32.5715
33.1246
34.9268
36.4364
37.0534
40.2131
42.3893
44.4152
45.4878
47.2275
54.4033
56.4471
75.3292
83.9728
9
10
11
12
13
14
15
16
17
18
19
20
21
22
47.2446
54.3872
56.4298
75.3317
83.9769
1.922356
1.685562
1.629297
1.260604
1.151451
4.36
5.48
2.95
3.45
◦
γ
α
Lattice parameters calculated: a=8.212 Å, b=8.212 Å, c = 16.97 Å and = β = = 90 ,
Particle size of complex 3b: 76 nm, V = 1144.26 Å3. (2Theta Zero Shift [◦], −0.01(6)).
Table 3. Experimental data and calculated results for the powder X-ray diffraction pattern of 3c,
hexagonal symmetry.
Peak no. 2 (c) [◦] 2 (o)[◦] d-sp. (c) [Å] d-sp. (o) [Å] Relative intensity (%)
hkl
θ
θ
1
2
3
4
5
6
7
8
12.6202 12.6337
21.9487 21.9512
25.3969 25.4268
27.4867 27.392
31.6927 31.7292
38.5047 38.5464
45.6151 45.4493
12.6202 12.6337
21.9487 21.9512
25.3969 25.4268
27.4867 27.392
7.008465
4.046339
3.504233
3.242368
2.820999
2.336155
1.987164
7.008465
4.046339
3.504233
3.242368
7.00105
100.00
7.20
21.24
12.40
71.49
8.12
7.57
4.02
1.36
2.19
200
220
400
211
311
600
112
200
220
400
211
4.045873
3.500174
3.253358
2.817842
2.333723
1.994027
7.00105
4.045873
3.500174
3.253358
9
10
11
1.49
◦
◦
γ
α
Lattice parameters calculated: a = 16.19 Å, b = 16.19 Å, c = 4.10 Å and = β = 90 , = 120
Particle size of complex 3c: 70 nm, V = 930.13 Å3. (2 Theta Zero Shift [◦], −0.0(1)).
3a, 3b and 3c correspondently, which could suggest that correspondently (Figure 4). Indeed, the combustion
all complexes are single-phase compounds.
process of complex 3a was achieved in two different
stages. The related DSC curve revealed intense exother-
mic peak at 664 ◦C in the temperature range 649–664 ◦C
followed by two successive endothermic peaks at 666
and 669 ◦C, respectively with an extrapolated combus-
tion enthalpy equal to −699.12 J.g−1. However, the
decomposition mechanism of 3b was carried out in two
similar stages. The corresponding DSC curve exhibited
3.2 DSC studies for the complexes 3a–c
The thermal curves exhibited slight endothermic peaks
nearly at 373 ◦C, 338 ◦C, and 299 ◦C for the complexes
3a, 3b, and 3c, respectively, which followed by heat
◦
◦
◦
flow gradually rise until 649 C, 652 C, and 646 C

J. Chem. Sci.
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Page 7 of 8
Supplementary Information (SI)
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180
160
140
120
100
80
3a
Supplementary Information for this article is available at
www.ias.ac.in/chemsci.
640
660
680
60
40
20
0
-20
Acknowledgements
0
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300
300
400
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250
200
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100
50
The authors wish to acknowledge the approval and the support
of this research study by the grant N◦. SCI-2017-1-7-F-6928
from the Deanship of Scientific Research in Northern Border
University, Arar, KSA.
3b
640
660
680
400
680
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References
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660
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-50
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-150
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Temperature (°C)
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4. Conclusions
Three monomeric pentacoordinate organotin(IV)
complexes were successfully synthesized and character-
ized using various analytical approaches. The results of
spectroscopic analyses were in agreement with the sug-
gested structures of the compounds. All the complexes
3a–c were obtained via O, N coordination to tin cen-
ter by their homologous ligands 2a–c, respectively. The
analysis of XRD spectra revealed that products 3a and
3b crystalize in the tetragonal system, while, the crystal
structure of complex 3c refers to the hexagonal system.
DSC studies showed that all the organotin compounds
3a–c possess higher thermal stability, a similar range
of decomposition temperature, and slightly comparable
combustion processes.
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