Synthesis and spectral studies (FT-IR, 1H, 13C, 119Sn, and mass spectrometry) of mixed organotin(IV) compounds containing a long chain alkyl group (n-C7H15)

Article abstract of DOI:10.1081/SIM-120030432

Di- and triorganotin(IV) compounds of the type R₂SnR ₂′ and R₃SnR′ (R = CH₃, n-C ₄H₉, C₆H₅, C₆H ₅CH₂ and R′ = n-C₇H₁₅) have been prepared by the reaction of R₂SnCl₂ and R ₃SnCl with a stoichiometric amount of n-heptylmagnesium bromide, prepared in situ in dry diethyl ether. The products obtained were vacuum distilled. The structural assignments were made on the basis of spectral studies such as FT-IR, ¹H, ¹³C, ¹¹⁹Sn NMR, and mass spectrometry which ascertain the tetrahedral environment around the tin atom.

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Synthesis and Spectral Studies (FT‐IR, 1H, 13C, 119Sn,
and Mass Spectrometry) of Mixed Organotin(IV)
Compounds Containing a Long Chain Alkyl Group
(n‐C7H15)
Sadiq‐ur‐Rehman a b , Saqib Ali a & Amin Badshah a
a Department of Chemistry, Quaid‐i‐Azam University, Islamabad, 45320, Pakistan
b Department of Chemistry, Azad Jammu and Kashmir University, Muzaffarabad, Pakistan
Published online: 16 Nov 2010.
To cite this article: Sadiq‐ur‐Rehman , Saqib Ali & Amin Badshah (2004): Synthesis and Spectral Studies (FT‐IR, 1H, 13C,
119Sn, and Mass Spectrometry) of Mixed Organotin(IV) Compounds Containing a Long Chain Alkyl Group (n‐C7H15), Synthesis
and Reactivity in Inorganic and Metal-Organic Chemistry, 34:3, 443-457
To link to this article: http://dx.doi.org/10.1081/SIM-120030432
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SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY
Vol. 34, No. 3, pp. 443–457, 2004
1
Synthesis and Spectral Studies (FT-IR, H,
13C, 119Sn, and Mass Spectrometry) of
Mixed Organotin(IV) Compounds
Containing a Long Chain
Alkyl Group (n-C7H15)
1
Sadiq-ur-Rehman,1,2 Saqib Ali,1, and Amin Badshah
*
1Department of Chemistry, Quaid-i-Azam University,
Islamabad, Pakistan
2Department of Chemistry, Azad Jammu and Kashmir University,
Muzaffarabad, Pakistan
ABSTRACT
Di- and triorganotin(IV) compounds of the type R2SnR02 and R3SnR0
(R ¼ CH3, n-C4H9, C6H5, C6H5CH2 and R0 ¼ n-C7H15) have been pre-
pared by the reaction of R2SnCl2 and R3SnCl with a stoichiometric
amount of n-heptylmagnesium bromide, prepared in situ in dry diethyl
ether. The products obtained were vacuum distilled. The structural assign-
ments were made on the basis of spectral studies such as FT-IR, 1H, 13C,
*
Correspondence: Saqib Ali, Department of Chemistry, Quaid-i-Azam University,
Islamabad 45320, Pakistan; E-mail: drsa54@yahoo.com.
443
DOI: 10.1081/SIM-120030432
0094-5714 (Print); 1532-2440 (Online)
www.dekker.com
Copyright # 2004 by Marcel Dekker, Inc.

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Rehman, Ali, and Badshah
119Sn NMR, and mass spectrometry which ascertain the tetrahedral
environment around the tin atom.
Key Words: Organotin(IV); n-Heptylmagnesium bromide; Spectra; Alkyl.
INTRODUCTION
In the past few decades the chemistry of tin has gained considerable
importance both in basic research and in industrial applications.[1,2] Organotin
compounds and intermediates are also used in organotin and organic syn-
thesis.[3,4] Thus, there are so many interesting aspects of inorganic and organic
tin chemistry that a continuous and intensive research is in progress in this
field.
Our contribution involves the synthesis, characterization,[5,6] structural
elucidation,[7–9] biological,[10,11] and industrial applications of orgariotin(IV)
compounds.[12–14] These compounds can be used as precursors for the syn-
thesis of triorganotin(IV) halides of moderate fungicidal activity.[15]
In continuation of our previous work,[16] we report here the synthesis, IR,
multinuclear NMR, and mass spectral studies of R2SnR02 and R3SnR0 where,
R0 ¼ n-C7H15 and R ¼ CH3, n-C4H9, C6H5, C6H5CH2.
RESULTS AND DISCUSSION
The tetraorganotin(IV) compounds with the general formula R42xSnRx0
have been synthesized by the reaction of n-heptylmagnesium bromide
(Grignard’s reagent) with the corresponding organotin(IV) chlorides. The
preparation of the compounds may be represented by the following general
equation.
R
4ꢀxSnClx þ nR0MgBr ꢀ! R4ꢀxSnR0x þ nBrMgCl
R ¼ CH3ð1Þ; n-C4H9ð3Þ; C6H5ð5Þ; C6H5CH2ð7Þ; R0 ¼ n-C7H15 x ¼ 2
R ¼ CH3ð2Þ; n-C4H9ð4Þ; C6H5ð6Þ; C6H5CH2ð8Þ; R0 ¼ n-C7H15 x ¼ 1
All the synthesized compounds are liquids, air-stable, and miscible with
common organic solvents. The physical data of compounds (1)–(8) are
given in Table 1.

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Rehman, Ali, and Badshah
Infrared Spectroscopy
The infrared spectra of the compounds were recorded as neat liquids in
the range 4000–400 cm21. The characteristic absorption frequencies are listed
in Table 2. The important and informative absorption bands are v(Sn–C)
stretching, v(C–H) stretching in CH2, CH3, v(C55C) bending in rings (in
aryl derivatives), and v(C–H) bending in CH2, CH3 which support the for-
mation of these compounds. The bands in the range 493–437 cm21 and
596–503 cm21 are assigned as vsym(Sn–C) and vasym(Sn–C), respectively.
These absorption bands indicate the formation of Sn–C bonds and are compa-
tible with literature values.[17] Similarly, the existence of vsym(C–H) and
vasym(C–H) stretching frequencies in CH2, v(C–H) bending in CH2, CH3 con-
firm the presence of n-C7H15 groups in all the synthesized compounds.
NMR Spectroscopy
The multinuclear NMR (1H, 13C, 119Sn) spectra were recorded in CDCl3,
using it as internal reference. The resonances are characterized by their multi-
1
plicity and coupling constants. The resonance frequencies for H, 13C, and
119Sn show good agreement with literature values.[18]
1H NMR
1
The H NMR spectral data recorded in CDCl3 are listed in Table 3.
A complex multiplet due to protons of long chain alkyl groups (both in
n-C7H15 and n-butyltin) is observed in the range 0.77–1.70 ppm. Therefore,
resonance peaks for protons of n-C7H15 and n-C4H9 are difficult to differen-
tiate in dibutyl- and trbutyltin derivatives. However, methyl (SnCH3) protons
of dimethyl- and trimethyltin derivatives appear as sharp singlets with well-
resolved coupling satellites due to tin. Similarly, methylene protons (SnCH2-
C6H5) of dibenzyltin derivative also give a sharp singlet with 2J[119Sn–1H] ¼
60 Hz at 2.39 ppm (Table 3). The coupling constants 2J[117/119Sn–1H]
observed for dimethyltin, trimethyltin, and dibenzyltin derivatives fall in the
range of a tetrahedral environment around the tin atom, which is further sup-
ported by the C–Sn–C bond angles (107.88, 108.48, 112.28) calculated by
Lockhart’s equation, respectively.[19] Due to complex multiplet pattern the
coupling constants 2J[117/119Sn–1H] are not observed for the other
compounds.
For phenyl- and benzyltin derivatives, ortho and para protons fall in the
range of 7.0–7.6 ppm and meta protons resonate at 7.2–7.8 ppm. Whereas,
signals for n-C7H15 protons appear in the region 0.9–1.9 ppm.

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Table 3. 1H NMR dataa for the synthesized compounds (in CDCl3).
Compound
no.
Chemical shifts (ppm), coupling constant (Hz)
(1)
0.09 [s, 6H, Sn(CH3)2]; 2J[117/119Sn–1H] ¼ 48.3, 50.4 Hz; 0.10
[s, 4H, Sn(CH2)2]; 2J[117/119Sn–1H] ¼ 48.3, 50.4 Hz; 0.87–
0.99 [m, 10H, 2CH2, 2CH3]; 1.36 [s, 12H, CH2]; 1.56–1.61
[m, 4H, CH2].
(2)
0.12 [s, 2H, SnCH2]; 2J[117/119Sn–1H] ¼ 50, 52.3 Hz; 0.13 [s, 9H,
Sn(CH3)3]; 2J[117/119Sn–1H] ¼ 50.1, 52.3 Hz; 0.89–0.99
[m, 5H, CH2, CH3]; 1.36 [s or brs, 6H, CH2]; 1.57–1.62 [m,
2H, CH2].
(3)
(4)
(5)
0.77–0.97 [m, 20H, Sn(CH2)4, 4CH3]; 2J[117/119Sn–1H] ¼ (n.o);
1.29–1.39 [m, 20H, CH2]; 1.43–1.53 [m, 8H, CH2].
0.87–0.96 [m, 20H, Sn(CH2)4, 4CH3]; 2J[117/119Sn–1H] ¼ (n.o);
1.27–1.41 [m, 18H, CH2]; 1.59–1.69 [m, 4H, CH2].
1.11–1.16 [m, 14H, Sn(CH2)4, 2CH3]; 2J[117/119Sn–1H] ¼ (n.o);
1.35–1.57 [m, 12H, CH2]; 1.61–1.94 [m, 4H, CH2]; 7.54–7.59
[m, 6H, o,p/H]; 7.69–7.79 [m, 4H, m/H].
(6)
(7)
1.14–1.16 [m, 7H, Sn(CH2)2, CH3]; 2J[117/119Sn–1H] ¼ (n.o); 1.55
[brs, 6H, CH2]; 1.77 [brs, 2H, CH2]; 7.37–7.49 [m, 9H, o,p/H];
7.56–7.59 [m, 6H, m/H].
0.87–1.03 [m, 14H, Sn(CH2)4, 2CH3]; 2J[117/119Sn–1H] ¼ (n.o);
1.32–1.39 [m, 12H, CH2]; 1.62–1.64 [m, 4H, CH2]; 2.39 [s,
CH2(Bz)]; 2J[117/119Sn–1H] ¼ 60 Hz, 7.01–7.10 [m, 6H, o,p/
H]; 7.23–7.36 [m, 4H, m/H].
2
(8)
0.98–1.0 [m, 7H, Sn(CH2)2, CH3]; J[117/119Sn–1H] ¼ (n.o); 1.39
[brs, 6H, CH2]; 1.59 [brs, 2H, CH2]; 2.37 [s, CH2(Bz)];
2J[117/119Sn–1H] ¼ (n.o), 7.13–7.39 [m, 9H, o,p/H]; 7.52–
7.59 [m, 6H, m/H].
as ¼ singlet; m ¼ multiplet, brs ¼ broad signal, (n.o) ¼ not observed, Bz ¼ benzyl.
13C NMR
The 13C NMR data of the compounds are given in Table 4. The number of
signals found corresponds to the number of expected magnetically nonequiva-
lent carbon atoms. The d 13C values for R groups in R42xSnR0xwhere, R¼alkyl
or aryl, were in the region reported in the literature.[6]
For n-C7H15, the magnetically nonequivalent carbons were assigned on
the basis nJ[117/119Sn–13C] values and an earlier report.[16] The coupling con-
stants 1J[117/119Sn–13C] observed in the spectra of compounds (1)–(8) lie in
the range 286–435 Hz and indicate a tetrahedral geometry around the
tin atom.[14]

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a
b
g
d
a
d

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Rehman, Ali, and Badshah
119Sn NMR
The 119Sn chemical shift data for the investigated compounds are pre-
sented in Table 4. The chemical shift values of 119Sn in four-coordinated tin
compounds range from 200 to 260 ppm[20,21] and the d 119Sn values for com-
pounds (1)–(8) are in agreement with these values. Thus, the results obtained
from 1H, 13C, and 119Sn NMR are consistent with each other and favor a tetra-
hedral geometry around the tin atom in all of the synthesized compounds.
Mass Spectrometry
The observed mass fragmentation pattern of R2SnR02 and R3SnR0 is
shown in Figs. 1 and 2, respectively. The most common fragments along
with their m/z ratios and relative abundances are given in Tables 5 and 6. A
molecular ion peak of low intensity was observed only in compounds (1),
(7), and (8). All of the R2SnR02 derivatives exhibit almost the same behavior
with the only exception of diphenyldi-n-heptyltin(IV). Here, the fragmenta-
tion proceeds via two pathways. The primary fragmentation may occur
Figure 1. Fragmentation pattern of R2SnR02.

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451
Figure 2. Fragmentation pattern of R3SnR0.
through loss of R or R0 and the secondary fragmentation involves
elimination of R00 (n-C7H14), following the b-hydrogen transfer mechan-
ism.[16] The tertiary fragmentþation is due to release of the corresponding
alkane (RH) generating [SnR0] or [SnR]þ. As a next step either one releases
R00 (n-C7H14) or Rꢁ (alkene), giving [SnH]þ as end product. Diphenyldi-n-
heptyltin(IV) adopts a different fragmentation pattern (Fig. 1) which leads
to the fragment [Sn]þ.
The fragmentation in R3SnR0 compounds also occurs by two different
pathways. All the derivatives show almost the same behavior. However, the
fragmentation pattern in triphenyl-n-heptyltin(IV) is slightly different from
that of other analogues (Fig. 2). In all the R3SnR0 derivatives the primary frag-
mentation is due to elimination of R groups while secondary and tertiary frag-
mentation occur through loss of R00 (n-C7H14) and corresponding alkane (RH),
respectively. A second pathway is characterized by loss of R0, followed by
release of corresponding alkene (Rꢁ) and alkane (RH) in subsequent steps.
In compounds (2), (6), and (8), the final step results in the elimination of an
R group and ends with [Sn]þ. But in compound (4) the final fragmentation
occurs via release of corresponding alkene (Rꢁ) again by the b-hydrogen
transfer mechanism and ends with [SnH]þ. In triphenyl-n-heptyltin(IV)
also the primary fragmentation is due to loss of R0. Then there is a successive

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Rehman, Ali, and Badshah

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Rehman, Ali, and Badshah
elimination of three R groups which ends with the fragment [Sn]þ of low
intensity.
EXPERIMENTAL
Chemicals
Organotin chlorides were obtained from Aldrich or Fluka Chemicals and
1-bromoheptane was obtained from Alfa Aesar Chemicals (Germany). Diben-
zyltin- and tribenzyltin chloride were prepared by a reported method.[22] The
solvents were dried before use.[23] All other chemicals were of analytical
grade and were used without further purification.
Instrumentation
Infrared spectra were recorded as neat liquids on a Bio-Rad Excalibur FT-
IR, model FTS 300 MX spectrometer (USA), in the frequency range 4000–
400 cm21 using KBr cells. NMR spectra (1H, 13C, 119Sn) were obtained on a
Bruker ARX 250 spectrometer (Germany), using CDCl3 as an internal refer-
ence [d 1H(CDCl3) ¼ 7.23 ppm; d 13C(CDCl3) ¼ 77.0 ppm]. 119Sn NMR spec-
tra were obtained with Me4Sn as external reference [d 119Sn ¼ 37.290665] as
reported earlier.[24] The mass spectral data were recorded on a MAT 8500 Fin-
nigan (Germany) mass spectrometer. The m/z values evaluation is based on the
assumption that H ¼ 1, C ¼ 12, and Sn ¼ 120.
Table 7. Experimental details.a,b
Compound
no.
General
formula
Molar
ratio
Mg
(g)
1-Bromoheptane
(mL)
R
(1)
(2)
(3)
(4)
(5)
(6)
(7)
(8)
R2SnR02
R3SnR0
R2SnR02
R3SnR0
R2SnR02
R3SnR0
R2SnR02
R3SnR0
CH3
CH3
1 : 2
1 : 1
1 : 2
1 : 1
1 : 2
1 : 1
1 : 2
1 : 1
1.120
0.610
0.770
0.370
0.730
0.320
0.260
0.120
7.30
3.98
4.99
2.40
4.86
2.10
1.70
0.80
n-C4H9
n-C4H9
C6H5
C6H5
C6H5CH2
C6H5CH2
aMolar ratio organotin(IV) chloride: 1-bromoheptane.
bR0 ¼ n-C7H15.

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455
Figure 3. Proposed structures (a) for R3SnR0 and (b) for R2SnR20 .
General Procedure of Synthesis
n-Heptylmagnesium bromide (12.7 mmol), prepared in situ was added
dropwise at 0 8C over a period of 30 min to a stoichiometric amount of the
corresponding organotin chloride (R2SnCl2, 25.4 mmols and R3SnCl,
12.7 mmol) suspended in 60 mL of toluene, under inert atmosphere (details
are given in Table 7). The reaction mixture was refluxed for 6 hr, cooled to
room temperature and hydrolyzed with 7% hydrochloric acid solution while
placed in an ice bath. The organic layer was separated and dried overnight
over anhydrous sodium sulfate. After filtration, solvent was evaporated on a
rotary evaporator. The product obtained was purified by vacuum distillation,
boiling points are included in Table 1.
From all of the spectroscopic studies, it is concluded that the synthesized
compounds have a tetrahedral environment around the tin atom in noncoordi-
nating solvents (Fig. 3).
ACKNOWLEDGMENTS
SA is thankful to Quaid-i-Azam University for financial support. SR is
indebted to the University of Azad Jammu and Kashmir for granting a
study leave.
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Received February 10, 2003
Accepted November 10, 2003
Referee I: G. Eng
Referee II: K. Moedritzer

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