Molecular structure and real-space bonding descriptors (AIM, ELI-D) of Phenyl(triphenylstannyl)telluride

Article abstract of DOI:10.1002/zaac.201300271

The previously known phenyl(triphenylstannyl)telluride, PhTeSnPh ₃, was prepared by the reaction of triphenyltin chloride, Ph ₃SnCl, with sodium phenyltellurolate, Na(TePh), in liquid ammonia. The molecular structure established by X

Full text of DOI:10.1002/zaac.201300271

SHORT COMMUNICATION
DOI: 10.1002/zaac.201300271
Molecular Structure and Real-Space Bonding Descriptors (AIM, ELI-D) of
Phenyl(triphenylstannyl)telluride
Jens Beckmann,*[a,b] Darina Heinrich, and Stefan Mebs*
[a]
[a]
Keywords: Tellurium; Tin; Density functional calculations; X-ray diffraction
Abstract. The previously known phenyl(triphenylstannyl)telluride, used for calculations of real-space bonding descriptors derived from
PhTeSnPh , was prepared by the reaction of triphenyltin chloride, an atoms-in-molecules (AIM) analysis of the theoretically calculated
Ph SnCl, with sodium phenyltellurolate, Na(TePh), in liquid ammonia. electron density. In addition, the electron localizability indicator
The molecular structure established by X-ray crystallography and by (ELI-D) was derived from the corresponding pair density and the
3
3
geometry optimization at the DFT/B3PW91/TZ level of theory was
Raub-Jansen-Index (RJI) was determined.
(ELI-D)[6] space partitioning schemes, respectively. The AIM-
approach has found wide applications in the last two dec-
Introduction
Studies involving the nature of chemical bonds are of utmost
concern for nearly all branches of chemistry. Small molecules
containing bonds between two distinctive p-block elements are
useful candidates for detailed bond analyses using real-space
bonding descriptors derived from the electron density (ED) and
[7]
ades, however, the ELI-D introduced in 2004 is not yet a
[1]
standard tool in the field. Besides our own work we are
aware of only one other study applying the ELI-D on tellurium
[8]
compounds.
the pair density. We recently reported an in-depth study on σ-
+
donor stabilized aryltellurenyl cations [MesTe(EPh )] (E = P, Results and Discussion
3
+
As, Sb) and [MesTe(TeMes )] , which are best described as
mesityltelluro-substituted triphenylphosponium, triphenylar-
sonium, triphenylstibonium, and dimesityl telluronium cations,
2
Phenyl(triphenylstannyl)telluride, Ph SnTePh, has been pre-
3
viously prepared by the reaction of PhTeTePh with Ph SnH in
3
yields of 50–70%[ and by the reaction of PhTeTePh with
2]
respectively, due to the fact that most of the positive charge is
[3]
situated at the donor atoms E.[1] Aryl(triphenylstannyl)tellu-
NaBH and Ph SnCl in yields of 76%, and characterized by
4 3
Raman, UV, NMR ( Sn, 125Te), and Mößbauer (119Sn, Te)
1
19
125
rides Ph SnTeR are isoelectronic to aryltelluro-substituted tri-
3
spectroscopy.[
3,4]
+
phenylstibonium cations [RTeSbPh ] , but lack a positive
3
We prepared Ph SnTePh by salt metathesis of Ph SnCl with
3
3
charge.
NaTePh (generated in situ from PhTeTePh and Na) in liquid
ammonia in 78% yield [Equation (1)]. The melting point
In this study, we extend the bond analysis to the previously
known phenyl(triphenylstannyl)telluride, Ph SnTePh, a simple
3
[
3]
119
125
molecule containing a Sn–Te bond.[
2–4]
(97 °C, lit. 95–97 °C ) as well as the Sn and Te NMR
The structural analysis
[4]
chemical shifts of –127.6 (lit. –125.0 ) and –202.5 (lit.
205.8 ) ppm resemble literature values and confirm the au-
based on X-ray crystallography is supported by density func-
tional theory (DFT) calculations performed at the B3PW91/TZ
level of theory. The experimental and theoretically optimized
[4]
–
thenticity of the material.
liquid NH
3
structures are topologically analyzed according to the Atoms-
Ph
3
SnCl + NaTePh
Ǟ
–NaCl
Ph
3
SnTePh
(1)
In-Molecules (AIM)[5] and Electron-Localizability-Indicator
The molecular structure of Ph SnTePh is shown in Figure 1
3
*
*
Prof. Dr. J. Beckmann
and selected bond parameters are collected in the caption of
the figure. The spatial arrangement of the tin atom is slightly
distorted tetrahedral with the C–Sn–C and C–Sn–Te angles
ranging from 108.2(2) to 110.3(2)°.
E-Mail: j.beckmann@uni-bremen.de
Dr. S. Mebs
E-Mail: stebs@chemie.fu-berlin.de
[
[
a] Institut für Chemie und Biochemie
Freie Universität Berlin
The Sn–Te–C angle of 90.2(1)° is identical within the exper-
Fabeckstraße 34/36
+
14195 Berlin, Germany
imental error to the Sb–Te–C angle of the MesTe(SbPh ) ]
3
3
b] Institut für Anorganische Chemie
Universität Bremen
[1]
cation. The Te–Sn bond length of 2.732(1) Å is slightly
+
Leobener Straße
longer than the Te–Sb bond length of the [MesTe(SbPh )]
3
28359 Bremen, Germany
[1]
cation [2.708(1) Å], which is presumably affected by the
positive charge and an additional ionic bond contribution aris-
ing thereof. There are no significant intermolecular contacts
Supporting information for this article is available on the WWW
under http://dx.doi.org/10.1002/zaac.201300271 or from the au-
thor.
Z. Anorg. Allg. Chem. 2013, 639, (12-13), 2129–2133
© 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
2129

J. Beckmann, D. Heinrich, S. Mebs
SHORT COMMUNICATION
3
Figure 3. Bond topology in the experimental geometry of Ph SnTePh.
[
11]
Figure 1. Molecular structure of Ph SnTePh showing 30% probability AIM2000 representation.
3
ellipsoids and the crystallographic numbering scheme. Selected bond
parameters /Å,°: Te1–Sn1 2.732(1), Te1–C1 2.134(5), Sn1–C7
2
1
.148(4), Sn1–C13 2.137(4), Sn1–C19 2.137(4), C7–Sn1–Te1
09.8(1), C13–Sn1–Te1 109.2(1), C19–Sn1–Te1 109.8(1), C7–Sn1–
The ELI-D basin volumes, charges, and attractor values for
the Te–Sn, Te–C, and Sn–C bonds and the lone-pair basins of
the tellurium atom [Te(LP)] are listed in Table 2. Overall, the
results are very similar to those for the previously analyzed
C13 110.3(2), C7–Sn1–C19 109.5(2), C13–Sn1–C19 108.2(2), C1–
Te1–Sn1 90.2(1). ORTEP representation.[
9]
+
+
[
MesTe(SbPh )] and [MesTe(TeMes )] cations uncovering
3 2
involving the tin and tellurium atoms. Starting from the experi-
mentally obtained atomic coordinates, a geometry optimization
was carried out. The superposition of the experimentally and
computationally obtained molecular structures is shown in Fig-
ure 2. The conformational differences are only marginal, which
may justify the sole analysis of the experimental geometry in
similar cases when theoretical geometry optimizations may not
[1]
all listed bond types as polar-covalent interactions. For the
ELI-D bonding basins (so called disynaptic valence basins)
also the attractor position relative to the atom–atom line and
[12]
the Raub-Jansen-Index are displayed.
The latter is a combi-
nation of the AIM and ELI-D partitioning schemes: It quanti-
fies the partial electron numbers of a ELI-D bonding basin
within the bond contributing AIM atoms. The RJI is 50% for
homopolar bonds and increases for polar interactions. Dative
bonds are represented by an RJI of at least 95%.[ The ELI-
D is displayed for two different iso values in Figure 4. At Y =
[1]
be feasible due to time constraints.
13]
1.4 the Te–Sn basin is not visible as the ELI-D value at the
attractor position is 1.34. The bonding electrons are much less
localized in the Te–Sn interaction than in the Te/Sn–C bonds,
which is reflected in the small value for the ED at the bond
critical point (bcp), the larger bond ellipticity (ε), the smaller
curvature along the bond path (λ ), the smaller localizability
3
value at the ELI-D attractor position of the Te–Sn basin (Ymax
)
and the larger distance of the ELI-D attractor position to the
atom–atom line (dELI).
The smaller difference of the electronegativity between tel-
lurium and tin compared to Te/Sn–C is reflected in the Lapla-
cian being close to zero (instead of being significantly posi-
tive), a smaller interpenetration of the tellurium and the tin
atom compared to Te/Sn and C, which gives rise to a smaller
G/ρ(r)bcp value for Te–Sn and a Raub-Jansen-Index (RJI) close
to 50%. With 1.55 e the electron population in the Te–Sn basin
is significantly smaller than in the related compounds compris-
ing Te–E (E = P, As, Sb) bonds (1.89–1.95 e) and comparable
Figure 2. Superposition of the experimentally obtained X-ray structure
(
(
light gray) and the computationally optimized gas-phase geometry
dark gray) of Ph SnTePh. SCHAKAL representation.
3
[
10]
+
[1]
to the Te–Te bond (1.61 e) of the [MesTe(TeMes )] cation.
2
The electronic analysis is focused on the Te–Sn, Te–C, and However, the ELI-D value at the attractor position, Ymax
=
Sn–C bonds and the involved atoms and lone pairs. The bond 1.34, is similar to the Te–Sb bond (1.32) and the Te–Te bond
+
+
topology of the experimentally obtained structure of (1.36) of the [MesTe(SbPh )] and MesTe(TeMes )] cat-
3
2
Ph SnTePh is shown in Figure 3. The corresponding bond to- ions.[ Integration of the electron population within the AIM
1]
3
pological parameters are collected in Table 1.
basins leads to AIM-atomic volumes and charges. Summing
2
130 www.zaac.wiley-vch.de
© 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 2013, 2129–2133

Phenyl(triphenylstannyl)telluride
Table 1. Bond topological propertiesa) of the Te–Sn, Te–C, and Sn–C bonds of Ph
second row (italics): values at computationally optimized gas-phase structure.
SnTePh. First row: values at experimentally obtained geometry,
3
Bond
d /Å
ρ(r)bcp /e·Å–3 Δρ(r)bcp /e·Å–5
d
1
/Å
d
2
/Å
ε
λ
3
/e·Å–5
G/ρ(r)bcp /he–1 H/ρ(r)bcp /he–1
Te1–Sn1
2.733
0.45
0.43
0.80
0.80
0.72
0.72
0.73
0.71
0.73
0.71
0.2
0.2
–0.2
0.0
2.6
2.7
2.9
2.7
2.9
2.9
1.462
1.476
1.098
1.097
1.090
1.090
1.084
1.090
1.084
1.091
1.271
1.284
1.037
1.037
1.057
1.059
1.052
1.060
1.053
1.062
0.15
0.16
0.05
0.03
0.07
0.07
0.06
0.06
0.06
0.06
2.53
2.40
5.76
5.80
8.15
8.18
8.50
8.17
8.55
8.14
0.37
0.35
0.50
0.50
0.68
0.69
0.71
0.69
0.71
0.69
–0.34
–0.33
–0.51
–0.51
–0.43
–0.43
–0.43
–0.43
–0.43
–0.42
2
.760
2.135
.134
2.147
.149
2.136
.150
2.137
.153
Te1–C1
Sn1–C9
Sn1–C15
Sn1–C21
2
2
2
2
a) For all bonds, ρ(r)bcp is the electron density at the bond critical point, Δρ(r)bcp is the corresponding Laplacian, d
from the atom to the bond critical point, ε is the bond ellipticity (ε = λ / λ
curvature along the bond path, G/ρ(r)bcp and H/ρ(r)bcp are the kinetic and total energy density over ρ(r)bcp ratios. Results obtained by an analysis
1
and d
2
are the distances
1
2 3
–1; λ1/2: curvatures perpendicular to the bond path), λ is the
[
11]
of the wavefunction files with AIM2000.
Table 2. Topological and integrated ELI-D propertiesa) of Ph
(
SnTePh. First row: values at experimentally obtained geometry, second row
italics): values at computationally optimized gas-phase structure.
3
Basin
V(001)ELI /Å3
N(001)ELI /e
Y
max
dELI /Å
RJI /%
Te–Sn
6.9
1.55
1.55
2.43
2.43
2.45
2.45
1.85
1.87
2.27
2.29
2.28
2.29
2.29
2.29
1.34
1.34
1.74
1.74
1.75
1.76
1.67
1.67
1.73
1.74
1.74
1.74
1.74
1.74
0.375
0.256
–
–
–
53
54
–
–
–
7
.3
21.0
1.1
21.7
1.6
4.6
.7
9.7
Te(LP1)
Te(LP2)
Te–C1
2
2
–
–
0.019
0.025
0.012
0.013
0.019
0.007
0.023
0.011
72
72
72
73
73
73
74
73
4
Sn–C7
10.0
Sn–C13
Sn–C19
9.7
10.0
9.5
10.1
a) For all basins, V(001)ELI is the basin volume cut at 0.001 a.u., N(001)ELI is the corresponding electron population in that volume, Ymax is
the ELI-D value at the attractor position, dELI is the perpendicular distance of the attractor position to the atom–atom line, RJI is the Raub-
Jansen-Index (percental electron population within the AIM atom, which has the larger electronegativity). Results obtained by analysis of grid-
[
20]
files using DGRID-4.5.
AIM-charges are analyzed for the experimentally obtained
structure of Ph SnTePh.
3
The molecular structure is divided into its functional frag-
ments: the tellurium atom (0.01 e), the phenyl ring attached to
the tellurium atom (–0.26 e), the tin atom (1.39 e) and the
three phenyl rings attached to the tin atom (–0.37 e, –0.38 e,
–
0.39 e). The relative distribution of charges in Ph SnTePh is
3
+
comparable to the distribution in the [MesTe(SbPh )] cation:
3
Te = 0.26 e, Ph(Te) = –0.09 e, Sb = 1.39 e, Ph(Sb) = –0.18
each.[ Thus, the positive charge in the [MesTe(SbPh )] cat-
1]
+
3
ion is quite equally distributed over all functional parts of the
molecule. According to the electronic real-space bonding prop-
erties the bond polarity of the Te–Sn interaction is lower than
Figure 4. Left side: Side-view ELI-D representation of the experimen-
tal X-ray structure of Ph
+
SnTePh (Y = 1.4) Small basins are light gray the Te–P, Te–As, Te–Sb bonds of the [MesTe(EPh
)
] cations
3
3
3
and solid, larger basins are increasingly dark gray and transparent. (E = P, As, Sb) and even the Te–Te bond in the
Right side: corresponding top view at Y = 1.3. The Te–Sn bonding
basin is also visible at this iso value. MOLISO representation.[14]
MesTeTeMes2]+ cation. The same trend is found for the
[1]
[
electron localization between the tellurium and the tin atom,
which is lower than the cationic reference compounds.
up atomic charges according to functional groups allows for
The Sn–Te bond in Ph SnTePh was investigated using real-
3
an analysis of electronic substituent effects. In this work, the space bonding descriptors derived from an atoms-in-molecules
Z. Anorg. Allg. Chem. 2013, 2129–2133
© 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.zaac.wiley-vch.de 2131

J. Beckmann, D. Heinrich, S. Mebs
AIM) analysis of the theoretically calculated electron density. Table 3. Crystal data and structure refinement of Ph SnTePh.
SHORT COMMUNICATION
(
3
Moreover, the electron localizability indicator (ELI-D) was de-
rived from the corresponding pair density and the Raub-
Jansen-Index (RJI) was determined. Unlike the strongly
polar Te–Te and Te–E bonds (E = P, As, Sb) of the previously
Formula
Formula weight /g·mol–1
Crystal system
24
C H20SnTe
554.69
monoclinic
0.70ϫ0.60ϫ0.50
Crystal size, mm
reported
σ-donor
stabilized
aryltellurenyl
cations Space group
P2 /c
12.951(4)
1
+
+ [1]
a /Å
b /Å
c /Å
α /°
[MesTe(TeMes )] and [MesTe(EPh )] , the Sn–Te bond of
2
3
9.434(4)
18.433(7)
90.00
106.09(3)
90.00
2163.9(14)
4
1.703
Ph SnTePh that is rather apolar. The structural differences of
3
molecular structures obtained experimentally by X-ray crystal-
lography and computationally by geometry optimization were
only marginally and consequently the analyses of the real- γ /°
β /°
3
V /Å
space bonding descriptors gave very similar results.
Z
ρ
calcd /mg·m–3
T /K
μ (Mo K
F(000)
θ range /°
Index ranges
173
2.506
1064
2.30 to 29.21
–17 Յ h Յ 11
Experimental Section
) /mm–1
α
The starting materials Ph
3
SnCl and PhTeTePh were commercial prod-
ucts and used as received. For general information refer to our preced-
ing paper.[
1]
–
–
12 Յ k Յ 10
25 Յ l Յ 25
Synthesis of Ph
with PhTeTePh (230 mg, 0.562 mmol) and cooled to –78 °C before
NH (30 mL) was condensed on. To the dark red solution, sodium
metal (34.1 mg, 1.48 mmol) was added, which caused a color change
to orange. After the mixture was stirred for 2 h, Ph SnCl (393 mg,
.12 mmol) was added and a colorless suspension was formed. The
mixture was allowed to warm up to room temperature, while the NH
3
SnTePh: A flame-dried Schlenk tube was charged
No. of reflns collected
Completeness to θmax
No. indep. reflections
No. obsd reflns with [I Ͼ 2σ(I)]
No. refined parameters
GooF (F )
13160
97.2%
5700
4494
236
3
3
1
2
1.013
0.108
3
Rint
slowly evaporated. The solid residue was extracted with THF R (F) [I Ͼ 2σ(I)]
0.0424
0.1238
Ͻ 0.001
0.927 / –1.503
1
2
(
2ϫ10 mL) and filtered. The slightly orange filtrate was evaporated wR
to dryness and the crude product was recrystallized from CH Cl /hex-
2 2
2
(F ) (all data)
Δ/σ)max
Largest diff peak/hole /e·Å
(
–
3
ane to give colorless crystals of Ph
8%).
3
SnTePh (486 mg, 0.88 mmol,
7
Supporting Information (see footnote on the first page of this article):
Cartesian coordinates of the optimized gas-phase structure of
Ph SnTePh.
3
X-ray Crystallography: Intensity data were collected with a STOE
IPDS 2T area detector fitted with graphite-monochromated Mo-K
α
(
0.7107 Å) radiation. The structure was solved by direct methods and
2
[15]
refined based on F using OLEX2.
All non-hydrogen atoms were
refined using anisotropic displacement parameters. Hydrogen atoms
attached to carbon atoms were included in geometrically calculated
positions using a riding model. Crystal and refinement data are col-
lected in Table 3.
Acknowledgements
The Deutsche Forschungsgemeinschaft (DFG) is gratefully acknowl-
edged for financial support.
Crystallographic data (excluding structure factors) for the structure in
this paper have been deposited with the Cambridge Crystallographic
Data Centre, CCDC, 12 Union Road, Cambridge CB21EZ, UK.
Copies of the data can be obtained free of charge on quoting the
depository number CCDC-940870 (Fax: +44-1223-336-033; E-Mail:
deposit@ccdc.cam.ac.uk, http://www.ccdc.cam.ac.uk).
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Published Online: August 15, 2013
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© 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.zaac.wiley-vch.de
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