The Nature of Chalcogen-Bonding-Type Tellurium–Nitrogen Interactions: A First Experimental Structure from the Gas Phase

Article abstract of DOI:10.1002/anie.202013480

(C₆F₅)Te(CH₂)₃NMe₂ (1), a perfluorophenyltellurium derivative capable of forming intramolecular N???Te interactions, was prepared and characterized. The donor-free reference substance (C₆F₅)TeMe (2) and the unsupported adduct (C₆F₅)(Me)Te?NMe₂Et (2 b) were studied in parallel. Molecular structures of 1, 2 and 2 b were determined by single-crystal X-ray diffraction and for 1 and 2 by gas-phase electron diffraction. The structure of 1 shows N???Te distances of 2.639(1) ? (solid) and 2.92(3) ? (gas). Ab initio plus NBO and QTAIM calculations show significant charge transfer effects within the N???Te interactions and indicate σ-hole interactions.

Full text of DOI:10.1002/anie.202013480

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Accepted Article
Title: The nature of chalcogen-bonding-type tellurium-nitrogen
interactions: a first experimental structure from the gas phase
Authors: Timo Glodde, Yury Vishnevskiy, Lars Zimmermann, Beate
Neumann, Georg Stammler, and Norbert Werner Mitzel
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The nature of chalcogen-bonding-type tellurium-nitrogen
interactions: a first experimental structure from the gas phase
Timo Glodde, Yury V. Vishnevskiy, Lars Zimmermann, Hans-Georg Stammler, Beate Neumann and
[
a]
Norbert W. Mitzel*
Dedicated to Professor Thomas M. Klapötke on the occasion of his 60th birthday
3
Abstract: (C
6
F
5
)Te(CH
2
)
3
NMe
2
(1), a perfluorophenyltellurium deriva-
spectrum shows a triplet ( J
Te,F
= 64 Hz) at 353 ppm. The fact that
the 125Te{ H} NMR resonance of Te(C F ) is a quintet at 305
1
tive capable of forming intramolecular N∙∙∙Te interactions, was pre-
pared and characterized. The donor-free reference substance
6
5 2
[10]
ppm allows to conclude the tellurium atom in 1 to be weakly
coordinated in solution –intra or intermolecularly– by an electro-
negative element such as nitrogen.
(C F
6
5
)TeMe (2) and the unsupported adduct (C
6 5 2
F )(Me)Te∙NMe Et
(2b)were studied in parallel. Molecular structures of 1, 2 and 2b were
determined by single crystal X-ray diffraction and for 1 and 2 by gas-
phase electron diffraction. The structure of 1 shows N∙∙∙Te distances
of 2.639(1) Å (solid) and 2.694(53) Å (gas). Ab initio plus NBO and
QTAIM calculations show significant charge transfer effects within the
N∙∙∙Te interactions and indicate -hole interactions.
Scheme 1. Synthesis of compound 1.
Dispersion interactions receive presently an increasing amount of
attention.[1] They can add the decisive component in stabilizing
otherwise weak interactions, e.g. halogen bonding (XB) sys-
tems.[2] Hitherto XB interactions were mainly studied by experi-
Suitable crystals for X-ray diffraction (XRD) of 1 were obtained by
sublimation. Its molecular structure in the solid (Figure 1) shows
a N∙∙∙Te distance of 2.639(1) Å. The distance from Te1 to the ipso-
carbon atom C1 of the perfluorophenyl unit is 2.189(1) Å; this is
rather long compared to bis(pentafluorophenyl)ditellane at
ments in the solid or in solution phase.[3] However, under these
conditions it is difficult to distinguish contributions to the strength
of this interaction from intermolecular dispersion or electrostatic
forces often summarized nonspecifically as “packing” or “solvent”
effects.[4] The determination of quantitative energies and a quali-
2.124(1) Å[11]
and bis(pentafluorophenyl)tellane[10] (2.101(6) Å)
and is explicable by population of the antibonding Te1–C1 orbital
by the donating nitrogen function in the NBO picture. As expected,
the angle C1–Te1–C7 at 91.3(1)° is close to 90°. The angle C1–
Te1∙∙∙N1 at 166.4(1)° deviates slightly from the expected 180° for
chalcogen bonding, likely due to ring restrictions.
The measured N∙∙∙Te distance is more than one Å shorter than
the sum of the van der Waals radii (r(vdW) = 3.65 Å).[12] The norma-
lized contact distance, i.e. the measured distance divided by the
tative interpretation of inter- and intramolecular interactions still
remain challenging tasks.[1] There is also still a distinct paucity in
corresponding gas-phase structure data because gas-phase ex-
periments and data analyses are generally much more challen-
ging and labor-intensive than such for the solid state.[5][6] The in-
vestigation of free molecules is, however, restricted in size, vola-
tility and thermal stability of the compounds, and in particular dif-
ficult if weak interactions are involved due to soft-potential
motions.
r(vdW), at 0.72 describes the interaction more properly.
In 1990 Singh et al. reported the existence of special N∙∙∙Te inter-
actions in tellurium(IV) derivatives with benzylamine ligands in the
solid phase.[7] The stabilizing effect was demonstrated by Ham-
merl et al. for the same benzylamine derivates[8] and Rakesh et al.
crystallized a system containing N∙∙∙Te-Cl units with a stronger
interaction between nitrogen and tellurium atoms (2.355(3) Å in
[9]
6 4 2 2
ClTe(o-C H )CH NMe ). In fact, the investigated systems de-
scribe donating interactions between the heavy atom tellurium
and the nitrogen atom, but a substantial proof in the gas phase is
still missing to exclude pure solid-state effects.
For this purpose we now prepared (N,N-dimethylaminopropyl)-
pentafluorophenyl)telluride (1) (Scheme 1). Its 125Te{ H} NMR
1
(
[
a]
T. Glodde, Dr. Yu. V. Vishnevskiy, L. Zimmermann, Dr. H.-G.
Stammler, B. Neumann, Prof. Dr. N. W. Mitzel
Universität Bielefeld, Fakultät für Chemie
Lehrstuhl für Anorganische Chemie und Strukturchemie
Universitätsstraße 25, 33615 Bielefeld, Germany
E-Mail: mitzel@uni-bielefeld.de
6
Figure 1. Molecular assembly of 1 in the crystal. The intermolecular Te1∙∙∙C -
ring centroid (Cnt’) distance of 3.662(1) Å and the C1-Te1-Cnt’ angle of 96.9(1)°
indicate a dimerization by weak intermolecular interaction in the solid state.
Symmetry code used for ‘: 1–x,1–y,1–z.
Supporting information for this article is given via a link at the end of
the document. CCDC 2007089-2007090 and 2022063
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COMMUNICATION
Since compound 1 is volatile and stable enough, we also perfor-
med a gas-phase electron-diffraction (GED) experiment in order
to determine a N∙∙∙Te distance for the free molecule. The obtained
GED data could be refined with a model that produced a sufficient
The intramolecular angle C1–Te1∙∙∙N1 is 178(7)°. This is in line
with an interpretation in terms of an undistorted classical -hole
interaction in the gas phase. Table 1 summarizes relevant struc-
tural parameters of compound 1 in the solid state and the gas
phase as well as such calculated by DFT at two different levels.
This allows to estimate the range of variation of theoretical data,
even if comparatively similar methods are chosen.
f
fit described by an R factor of 4.1 %. The GED analysis (Figures
2
and 3) shows a single conformer to be sufficient to describe the
data in the refinement properly.
The M06-2x[ DFT level of theory was the starting point for in-
vestigations with the NBO and QTAIM concepts. The NBO analy-
sis[18] found an n→* donation from N to Te associated to an NBO
17]
In the gas phase, the N∙∙∙Te distance refines to 2.91 Å with an
error of 3of 0.03 Å (3 errors are used throughout this article for
GED parameters). The large standard deviation of the N∙∙∙Te dis-
tance arises from the complex atomic electron scattering functi-
ons[13] of heavy atoms like Te. Haaland found this to result in an
intrinsically low signal to background ratio during the analysis of
−
1
stabilization energy of 7.2 kcal mol . The p-type orbital located at
the Te atom donates electron density into the-system of the
−
1
C F unit leading to an NBO stabilization energy of 7.2 kcal mol .
6
5
[14]
Te(CH
3
)
2
.
The N∙∙∙Te distance is longer than in the solid state
(
2.639(1) Å), but still shorter than r(vdW), the normalized contact
distance is 0.80±0.02. This underlines the impact of a relatively
strong non-covalent interaction. The fact that the weak N∙∙∙Te
bond is shorter in the solid than in the gas phase is in line with a
significant donor acceptor contribution as is frequently observed
for datively bonded systems.[15,16] The weaker N∙∙∙Te interaction
in the gas phase is also consistent with a shorter Te1–C1 bond,
due to a less pronounced donation into the antibonding Te1–C1
orbital (lp(N)→*(Te–C)).
The possibility of multiple conformers or dynamic systems in the
gas phase have been explored, and any attempts to account for
them do not lead to an improvement of the results.
Figure 3. Gas-phase structure of 1 as determined by gas electron diffraction.
Table 2. Selected intramolecular topological charge density parameters from
the QTAIM analysis for compound 1. Charge densities (e Å−3), Laplacian
2(e Å−5), ellipticities (dimensionless) and bond path length BPL (Å).
2
Bond
(BCP)
– (BCP)

BPL / Å
Te1–C1
Te1–C7
N1∙∙∙Te1
0.79
0.80
0.17
–5.18
–1.34
–1.60
0.19
0.18
0.08
2.040
2.076
2.852
1
An analysis according to the Quantum Theory of Atoms in Mole-
cules (QTAIM, Table 2) provides a small value for the charge
density at the bond critical point (BCP) of the N∙∙∙Te interaction of
−
3
2
0
.17 e Å . The corresponding Laplacian – (Te,N) has a very
small negative value; this confirms that this interaction can be
characterized as borderline between open and closed shell.[ In
contrast to these findings, earlier studies of comparable systems
found no bond critical point between donor and acceptor atoms.[
To further explore these non-covalent interactions, we studied the
nitrogen-free methyl(pentafluorophenyl)telluride (2) as a referen-
ce compound. Compound 2 was first described by Klein et al. but
it was only characterized by its 19F NMR spectrum and was then
19]
16]
Figure 2. GED radial distribution curve of compound 1. The circles represent
experimental data, while the line represents the used model. The lower curve
represents the difference curves between experiment and model.
Table 1. Summary of the most relevant structural parameters of compound 1.
The errors for the GED parameters are given as 3for XRD 1The parameter
notation follows the crystallographic labels.
prepared from dimethyltellurium and iodopentafluorobenzene by
irradiation with light.[20] We established a new synthesis for 2
using an alternative and rational approach: the reaction of lithium
methyltelluride with bromopentafluorobenzene (Scheme 2).
Method
Phase
XRD
solid
e
GED (r )
gas
PBE0-D3a,c
M06-2xb,c
d(Te1–C1) / Å
d(Te1–C7) / Å
2.189(1)
2.159(1)
2.639(1)
166.4(1)
91.3(1)
2.144(7)
2.151(9)
2.91(5)
161(2)
2.150
2.159
2.751
165.8
92.0
2.076
2.112
2.899
162.9
92.2
d(N1∙∙∙Te1) / Å
α(N1∙∙∙Te1–C1) / °
α(C1–Te1–C7) / °
88.6(7)
a
PBE0-D3/def2-TZVP, b M06-2x/def2-TZVPP, c single molecule
Scheme 2. Synthesis of 2
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Figure 5. Experimental (dots) and model (line) radial distribution curves of 2.
The lower curve represents the difference curve (experiment−model).
Figure 4. Molecular assembly of compound 2 in the solid state, view along the
a-axis. Symmetry codes: ‘ 1–x,–y,–½+z; ‘‘ 1–x,–y,½+z.
1
Table 3. Summary of the most relevant structural parameters of compound 2.
The errors for the GED parameters are given as 3for XRD 1
The H NMR spectrum of 2 shows a signal at 2.31 ppm while the
1
25
Te NMR spectrum of 2 shows a triplet of quartets at 210 ppm
Te,F 32 Hz), indicating the presence of a two-coordinate tellu-
(3
J
Method
Phase
XRD
solid
e
GED (r )
gas
2
PBE0-D3a,c
M06-2xb,c
rium atom. The quartet results from a JTe,H coupling to the three
hydrogen atoms of the methyl group. The 13C NMR spectrum of 2
reveals a triplet at −16 ppm with a 3JF,C coupling constant of 4 Hz
d(Te1–C1) / Å
d(Te1–C7) / Å
2.120(1)
2.138(2)
94.3(1)
2.077(16)
2.164(29)
93(3)
2.106
2.136
96.3
2.044
2.105
93.8
which is assigned to the methyl group. Furthermore, the signal
related to the ipso-carbon atom shows a triplet of quartets at 84
ppm. The triplet arises from the 2JF,C coupling with a coupling con-
α( ̛C 1–Te1–C7) / °
a
PBE0-D3/def2-TZVP, b M06-2x/def2-TZVPP; c single molecule
stant of 32 Hz and the quartett from a 3
JC,H coupling with the
methyl group with a coupling constant of 4 Hz.
We were able to crystallize compound 2 using in-situ crystalliza-
tion techniques. The crystal structure of 2 (Figure 4) shows end-
Table 4. Selected topological charge density parameters from the QTAIM ana-
lysis for compound 2a and 2b. Charge densities (e Å−3), the Laplacian – (e
Å
2
−5), ellipticities (dimensionless) and bond path length BPL (Å).

less chains (2) linked by Te∙∙∙Te interactions (3.761(1) Å long),
indicating the presence of chalcogen bonding. This is confirmed
2
Bond
ρ(BCP)
– ρ(BCP)
ε
BPL / Å
by the direction of the Te–Cipso bond, which points with angles of
C1–Te1
C7–Te1
Te1 ∙∙∙Te1’
C1–Te1
C7–Te1
N1∙∙∙Te1
0.73
0.74
0.08
0.69
0.75
0.17
–3.80
–1.10
–0.75
–2.06
0.16
0.17
0.16
0.15
0.18
0.17
0.24
2.120
2.138
3.776
2.124
2.108
2.808
164.8(1)° for C1-Te1∙∙∙Te1’ and 122.4(1)° for C1-Te1∙∙∙Te1’’ onto
2
a
the tellurium atoms of the neighboring molecules (crystallogra-
phically generated by two-fold screw axes). The Te1–C1 distance
in solid 2 is 2.119(1) Å and the Te1–C7 distance 2.137(2) Å.
The gas-phase structure of compound 2 was determined by GED
2b
(
Figure 5). Table 3 summarizes selected important structural pa-
–1.40
rameters in comparison to solid state and theoretical values. The
gas-phase data reveal a Te1–C1 distance of 2.077(16) Å, a Te1–
C7 distance of 2.164(29) Å and a C1–Te1–C7 angle of 93(3)°.
The above discussed problem of the complex scattering functions
has its impact and results in large estimated standard deviations.
The obtained structural parameters for compound 2 show that the
Te1–C7 distance is the same in the gaseous and solid phase with-
in experimental error, whereas the Te1–C1 distance is shorter in
the solid state. The latter results from the intermolecular Te∙∙∙Te
interaction in the crystal (see above), which is absent in the gas
phase. Besides the different bond lengths, the angle C1–Te1–C7
is the same in gaseous and solid state within error ranges.
In order to compare this Te∙∙∙Te-bonded with an –in contrast to 1–
unsupported N∙∙∙Te-bonded situation and to describe the strength
2
of a potential chalcogen bond better, a cocrystal of 2 with Me NEt
was generated (complex 2b) and examined by XRD. The unsup-
ported N∙∙∙Te contact measures 2.854(1) Å and the Te1–C1
distance is 2.160(1) Å (more information see SI).
The availability of various chalcogen bonding situations in com-
pounds 2, 2a and 2b provoked quantum-chemical studies to be
performed on the relevant sections of the experimental crystal
structures at the M06-2x/def2-TZVPP level (single molecules of 2,
a section of the (2)
 2
chain: the dimer (2) denoted 2a, and complex
2b; only H-atoms were optimized). The natural population ana-
lyses (NPA) show slightly smaller positive charge at the tellurium
atom of 2 (0.54 e) compared to that in 1 (0.56 e). The most impor-
tant contributions of the NBO analyses are donations of the nitro-
gen lone pair into the antibonding Te1-C1 orbital lp(N)→*(Te1-
−1
C1) (for 1: 7.2, for 2b: 9.1 kcal mol ) and a donation of the p-type
lone pair located at the tellurium atom into the -system of the
6 5
C F unit, lp(Te, 5p)→*(Te1-C1), for 1, 2, 2a and 2b (1: 7.2, 2:
−
1
4
.0, 2a: 4.0, 2b: 3.5 kcal mol ). The Quantum Theory of Atoms in
Molecules (QTAIM, Table 4) provides the same small values for
−3

at the BCPs of the Te∙∙∙N bonds in 1 and 2b (both 0.17 e Å )
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Angewandte Chemie International Edition
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COMMUNICATION
−
3
and an even smaller value for the Te∙∙∙Te bond in 2a (0.08 e Å ).
both, solid and gas phase, underlining the structurally determining
importance of the interaction between N and Te atoms. The inter-
actions can be explained by the electron-accepting behavior of
2
The Laplacian values –  at these BCPs adopt small negative
−
5
values (1: –1.6, 2b: –1.4, 2a: –0.8 e Å ) indicating a depletion of
electrons, compatible with more closed-shell-type, i.e. dative
interactions.
6 5 3 6 5
the -TeC F unit. This was further confirmed with H CTeC F (2)
showing an intermolecular Te···Te’ distance of 3.761(1) Å in the
solid state. This fact is explicable by the simultaneously donating
and accepting behavior of the Te atom, the latter is induced by
the -C F group. Quantum-mechanical studies prove the inter-
6 5
actions observed in 1 and 2 to arise from to the same origin.
Using the WFA Surface Analysis Suite[21] it was possible to deter-
mine the maximum of the electrostatic potential on the charge-
density isosurface (Vs,max) of 29 kcal mol− for the isolated mole-
cule 2 (Figure 6). It is located coaxial the Te1–C1 bond and repre-
sents a -hole. Two of the observed local minima of the electro-
static potential on the charge-density isosurface (Vs,min) of com-
pound 2 are located at the tellurium atom and indicate the positi-
1
Acknowledgements
This work was funded by DFG (German Research Foundation) in
the Priority Program SPP1807 “Control of LD in molecular chemi-
stry”, grant MI477/28-2, project no. 271386299), the core facility
GED@BI (grant MI477/35-1, project no. 324757882) and a grant
to Yu.V.V (VI 713/1-2, project no. 243500032). The authors grate-
fully acknowledge computing time provided by the Paderborn
Center for Parallel computing (PC2).
2 2
ons of the lone pairs in an AX E geometry (VSEPR model).
These regions of Vs,min/Vs,max at the calculated surface are compa-
rable to the interacting regions in the molecular assembly in the
solid state (Figure 4). This explains the crystallization behavior of
2: each tellurium atom acts on one hand as a donor with its lone
pair resulting in a C1-Te1-Te1’’ angle of 122.4(1)° and on the
other hand simultaneously with its -hole as acceptor resulting a
C1-Te1-Te1’ angle of 164.8(1)°. This leads also to the conclusion,
that the surface potential of an isolated molecule 2 is high enough
to interact with Lewis-basic regions (e.g. of amines), as was
demonstrated with 1 and 2b.
Keywords: gas phase electron diffraction • chalcogen bonding •
intermolecular interactions • -holes
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–1
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Angewandte Chemie International Edition
10.1002/anie.202013480
COMMUNICATION
COMMUNICATION
Willing to interact are the
tellurium and nitrogen atoms
of Me N(CH ) Te(C F ) as
2 2 3 6 5
T. Glodde, Y. V. Vishnevskiy, L. Zimmer-
mann, H.-G. Stammler, B. Neumann and N.
W. Mitzel*
was experimentally proven
both, in the solid state and
the gas phase.
Page No. – Page No.
The nature of chalcogen-bonding-type tellu-
rium-nitrogen interactions: a first experimen-
tal structure from the gas phase
This article is protected by copyright. All rights reserved.