Crystal structures and chemical properties of dimesitylcadmium and dimesitylmercury

Article abstract of DOI:10.1002/zaac.201100049

Mesityllithium was used to synthesize dimesitylcadmium and dimesitylmercury from CdCl₂ and HgCl₂, respectively. X-ray- crystallographic data show that the group 12 metal compounds M[Mes]₂ (M = Zn, Cd, Hg) are isomorphous (monoclinic, P2₁/n). The asymmetric unit of M[Mes]₂ (M = Zn, Cd, Hg) consists of one mesityl group bonded to the metal atom, which is related to the second substituent by an inversion center. In addition we have investigated the reaction of BBr₃ with M[Mes]₂ (M = Cd, Hg) for our understanding of the reactivity of donor-free group 12 mesityl compounds. The reaction of M[Mes]₂ (M = Cd, Hg) with an excess of BBr₃ produces MesBBr₂. UV-induced conversion of Hg[Mes]₂ in benzene yielded quantitatively mesitylene and mercury whereas irradiation of a chloroform solution of Hg[Mes]₂ for 1290 min (λ_max = 510 nm) gave mesitylene, Hg[Mes]Cl, and HgCl₂ in a ratio of 6:4:1. Slow concentration of the reaction solution led to the deposition of X-ray quality crystals of the addition compound of two Hg[Mes]Cl molecules and HgCl ₂ (monoclinic space group P2₁/n).

Full text of DOI:10.1002/zaac.201100049

SHORT COMMUNICATION
DOI: 10.1002/zaac.201100049
Crystal Structures and Chemical Properties of Dimesitylcadmium and
Dimesitylmercury
[a]
[a]
[a]
[a]
Mari Hayashi, Michael Bolte, Matthias Wagner, and Hans-Wolfram Lerner*
Keywords: Mesityl; Cadmium; Mercury; Photochemistry; Crystal Structure
Abstract. Mesityllithium was used to synthesize dimesitylcadmium M[Mes]
and dimesitylmercury from CdCl and HgCl , respectively. X-ray-crys- UV-induced conversion of Hg[Mes]
tallographic data show that the group 12 metal compounds M[Mes] mesitylene and mercury whereas irradiation of a chloroform solution
M = Zn, Cd, Hg) are isomorphous (monoclinic, P2 /n). The asymmet- of Hg[Mes] for 1290 min (λmax = 510 nm) gave mesitylene,
ric unit of M[Mes] (M = Zn, Cd, Hg) consists of one mesityl group Hg[Mes]Cl, and HgCl in a ratio of 6:4:1. Slow concentration of the
bonded to the metal atom, which is related to the second substituent reaction solution led to the deposition of X-ray quality crystals of the
by an inversion center. In addition we have investigated the reaction addition compound of two Hg[Mes]Cl molecules and HgCl (mono-
of BBr
2
(M = Cd, Hg) with an excess of BBr
3 2
produces MesBBr .
in benzene yielded quantitatively
2
2
2
2
(
1
2
2
2
2
3
2 1
with M[Mes] (M = Cd, Hg) for our understanding of the clinic space group P2 /n).
reactivity of donor-free group 12 mesityl compounds. The reaction of
Introduction
Results and Discussion
Since the first synthesis of dimesitylmercury in 1895 by
Our group has recently reported on the chemical and struc-
Michaelis many applications of synthesized diarylmercury tural features of group 12 compounds of the type MR2.[
compounds have been documented.[1] Despite the long exis- On the basis of these previous investigations we are now inter-
tence and common usage of dimesitylmercury, its structure has ested in the solid-state structures of donor-free dimesitylcad-
not yet been investigated well. However, detailed structural in- mium and dimesitylmercury. As shown in Scheme 1, we could
formation concerning the extent of coordination and associa- synthesize solvent-free M[Mes] (M = Cd, Hg) when MCl
7–10]
2
2
[
11]
tion in organometallic compounds is important in understand- (M = Cd, Hg) was treated with two equivalents of Li[Mes]
ing their physical behavior and chemical reactivity.
in thf at ambient temperature. The mesityllithium was com-
Due to its prominence, several preparation routes to pletely consumed overnight, (as determined by NMR spectro-
Hg[Mes] have been described in the literature: (i) dimesitylm- scopy). Changing the solvent to benzene, filtering, and slowly
2
ercury was obtained from the reaction of MesBr and sodium concentrating the filtrate leads to the deposition of X-ray qual-
amalgam,[ (ii) Hg[Mes] could also be synthesized by the ity crystals of solvent-free M[Mes] (M = Cd, Hg).
1]
2
2
[2,3]
reaction of HgCl with MesMgBr in a 1:2 stoichiometry,
We found that M[Mes] (M = Cd, Hg) organyl compounds are
2
2
(
iii) the reaction of the diazonium chloride MesN Cl with cop- much less moisture-sensitive than mesityllithium. Moreover, in
2
[4]
per in the presence of HgCl yielded Hg[Mes] , and at last
2
2
(
iv) the dimesitylmercury could be prepared by reaction of the
[5]
boronic acid MesB(OH) with Hg[OAc] . In contrast to the
2
2
long-standing known preparation routes of Hg[Mes] , the first
2
synthesis of the corresponding cadmium compound Cd[Mes]
2
[6]
has been reported very recently.
In this paper we report for the first time the structures of
solvent-free, unsupported Cd[Mes] and Hg[Mes] . In addition
2
2
we present here the reactivity of M[Mes] (M = Cd, Hg) to-
2
wards BBr and we describe the UV-induced decomposition
3
reaction of Hg[Mes]2.
*
Dr. H.-W. Lerner
Fax: +49-69-79829260
E-Mail: lerner@chemie.uni-frankfurt.de
[
a] Institut für Anorganische Chemie
Goethe-Universität Frankfurt
Max-von-Laue-Str. 7
Scheme 1. Synthesis of M[Mes]
2
(M = Cd, Hg) and UV-induced de-
2
60438 Frankfurt, Germany
composition reaction of Hg[Mes] .
6
46
© 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 2011, 637, 646–649

Dimesitylcadmium and Dimesitylmercury
the literature it was reported that no reaction has taken place the caption of Figure 2 and Table 1. The addition compound
[
1]
between Hg[Mes] and Brønstedt acids like HCl. In our study Hg[Mes]Cl·0.5 HgCl2 crystallizes in the monoclinic space
2
we investigated the reaction of M[Mes] (M = Cd, Hg) with the group P2 /n with one half molecule in the asymmetric unit,
2
1
Lewis acid BBr . The reaction of M[Mes] (M = Cd, Hg) with which is related to its second half via a crystallographic inver-
3
2
[
16]
an excess of BBr produces MesBBr .
However, in both sion center (Hg(2) atom in Figure 2). The Hg–C bond
3
2
cases a reddish precipitate was formed additionally. We found
that M[Mes] (M = Cd, Hg) are light-sensitive compounds.
2
When a benzene solution of Hg[Mes] was irradiated with a
2
high-pressure mercury lamp (λmax = 510 nm), a gray-metallic
1
13
precipitate formed. After 690 min the H and C NMR spectra
of the reaction solution revealed exclusively signals which
could be assigned to mesitylene. However, in chloroform UV-
induced conversion of Hg[Mes] took another course than in
2
benzene. When a chloroform solution of Hg[Mes] was irradi-
2
ated for 1290 min (λmax = 510 nm), mesitylene, Hg[Mes]Cl,
and HgCl were formed in a 6:4:1 ratio (Scheme 1). Slow con-
2
centration of the reaction solution led to the deposition of X-ray
quality crystals of the addition compound of two Hg[Mes]Cl
molecules and HgCl . In this context it should be noted when
2
a chloroform solution of Hg[Mes] was irradiated for 130 h,
2
[12]
mesitylene and HgCl could be isolated.
2
X-ray quality crystals of M[Mes] (M = Cd, Hg) were grown
2
Figure 1. Molecular structure of Hg[Mes]
2
in the solid state. Selected
from benzene. The solid-state structures of the homologues
bond lengths /Å and bond angles /°: Hg(1)–C(1) 2.080(6), C(1)–C(2)
[13]
M[Mes] (M = Zn,
Cd, Hg) resemble each other closely.
2
1.409(9), C(1)–C(6) 1.413(8), C(2)–C(3) 1.407(10), C(2)–C(7) 1.492(9),
Moreover the group 12 metal compounds M[Mes] (M = Zn, C(3)–C(4) 1.392(9), C(4)–C(5) 1.391(10), C(4)–C(8) 1.514(9), C(5)–
2
Cd, Hg) are isomorphous and crystallize in the monoclinic C(6) 1.384(9), C(6)–C(9) 1.510(9); C(1)#1–Hg(1)–C(1) 179.999(1). Se-
lected bond lengths /Å and bond angles /° of Cd[Mes]
2
: Cd(1)–C(1)
space group P2 /n. Since Cd[Mes]2 is isomorphous to
1
2
1
1
.114(7), C(1)–C(6) 1.395(9), C(1)–C(2) 1.396(10), C(2)–C(3)
Hg[Mes] , only dimesitylmercury is depicted (Figure 1). Se-
2
.421(12), C(2)–C(7) 1.499(11), C(3)–C(4) 1.374(11), C(4)–C(5)
.385(11), C(4)–C(8) 1.512(10), C(5)–C(6) 1.412(10), C(6)–C(9)
lected bond lengths and angles for all structurally characterized
M[Mes] (M = Cd, Hg) compounds can be found in Table 1 1.510(11); C(1)–Cd(1)–C(1)#1 179.999(1). Symmetry transformation
2
used to generate equivalent atoms: #1 –x, –y + 1, –z + 1.
and in the caption of Figure 1. The asymmetric unit of
M[Mes] (M = Zn, Cd, Hg) consists of one mesityl group
2
bonded to the metal atom, which is related to the second sub-
stituent by an inversion center. Consequently, the central C– Table 1. Selected bond lengths /Å of unsupported Li[Mes] and
M[Mes]
Mg[Mes]
2
(M = Zn, Cd, Hg) as well as of supported Hg[Mes]Cl and
2
M–C unit is strictly linear in M[Mes] (M = Zn, Cd, Hg) and
2
.
the two aryl groups are coplanar with respect to each other. In
this context it should be noted that a characteristic feature of
M–Ca)
M–Cb) C=Cc)
C–CH
c)
3
group 12 compounds of the type MR with bulky ligands (e.g. Li[Mes][
11]
2
2.16
1.94
2.11
2.08
2.05
2.17
2.40
3.73
3.66
3.75
3.32
5.72
1.40
1.39
1.40
1.40
1.40
1.40
1.53
1.52
1.51
1.51
1.51
1.52
R = SitBu3,[ Si(SiMe3)3,
7]
[15]
[9]
[13]
N(SiMe3)2 ) is the linearity of Zn[Mes]
2
Cd[Mes]
2
the E–M–E bond axis. However, the central E–M–E units in
the solid-state structures of M[SiH(SitBu ) ] (M = Zn, Cd,
Hg[Mes]
Hg[Mes]Cl
[Mg(thf)
][Mes] [
2
3
2 2
d)
Hg)[ and Zn[PtBu2]
8]
[10]
deviate from linearity due to interac-
16]
2
2
2
tions between the metal atoms with H–Si bond in
M[SiH(SitBu ) ] and between the zinc atom with the lone pair
a) Intramolecular, b) intermolecular, c) average, d) supported with 0.5
3
2 2
equivalent of HgCl .
2
of the phosphorus atom in Zn[PtBu ] , respectively. The struc-
2
2
tures of M[Mes] (M = Zn, Cd, Hg) and Hg[Mes]Cl reveal
2
weak contacts from the carbon atoms of the mesityl rings to
the metal atoms of neighboring molecules. These M–C distan-
ces (>3.3 Å) are much longer than the shortest intermolecular
Li–C contacts in Li[Mes] (Table 1). In Table 1 the metrical
parameters of unsupported M[Mes] (M = Zn, Cd, Hg) and
2
supported Hg[Mes]Cl have been compared with those of solv-
ate-free mesityllithium[ 16]and thf complexed dimesitylmagne- Figure 2. Molecular structure of Hg[Mes]Cl·0.5HgCl
11]
in the solid state.
2
[
Selected bond lengths /Å and bond angles /°: Hg(1)–C(1) 2.045(12),
Hg(1)–Cl(1) 2.348(3), Cl(1)–Hg(2) 2.969(3), C(1)–C(2) 1.407(16),
C(1)–C(6) 1.436(16), C(2)–C(3) 1.373(18), C(2)–C(7) 1.519(16), C(3)–
C(4) 1.382(17), C(4)–C(5) 1.382(17), C(4)–C(8) 1.484(18), C(5)–C(6)
sium [Mg(thf) ][Mes] .
2
2
X-ray quality crystals of Hg[Mes]Cl·0.5HgCl were grown
2
from the reaction solution at ambient temperature. Selected
bond lengths and angles for Hg[Mes]Cl·0.5HgCl are found in 1.400(16), C(1)–Hg(1)–Cl(1) 172.6(3).
2
Z. Anorg. Allg. Chem. 2011, 646–649
© 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.zaac.wiley-vch.de
647

M. Hayashi, M. Bolte, M. Wagner, H.-W. Lerner
SHORT COMMUNICATION
[
2.045(12) Å] in Hg[Mes]Cl·0.5 HgCl is somewhat shorter was irradiated with a high-pressure mercury lamp (λmax = 510 nm) for
2
1290 min. An accompanying change of the color of the solution from
than the corresponding bond lengths in Hg[Mes] , as shown in
2
1
13
colorless to yellow was observed. The H and C NMR spectrum of
the reaction solution revealed signals that could be assigned to mesity-
lene and Hg[Mes]Cl in a ratio of 6:4. In order to prove this result we
analyzed the reaction solution additionally by gas chromatography.
Slow concentration of the solution led to the deposition of X-ray qual-
Table 1.
Experimental Section
All experiments were carried out under dry argon or nitrogen using ity crystals of Hg[Mes]Cl·0.5HgCl2 at ambient temperature [Yield:
standard Schlenk and glove box techniques. Chloroform was dried 1 mg (61 %)].
2
with CaH and freshly distilled prior to use. Benzene and thf were
Hg[Mes]Cl: M.p.: 157 °C. C
9
H
11ClHg (355.23): C, 30.43, H, 3.12,
distilled from sodium/benzophenone. Li[Mes] was prepared according
1
to a published procedure.[ All other starting materials were pur-
chased from commercial sources and used without further purification.
NMR spectra were recorded with a Bruker DPX 250, a Bruker Avance
11]
Found C, 32.00, H, 3.44%. H NMR (300.0 MHz, CDCl ): δ =
3
6
.97 (m, 2 H, meta-Ph), 2.45 (br., 6 H, ortho-Me), 2.31 (br., 3 H, para-
13
1
Me). C{ H} NMR (75.5 MHz, CDCl
3
): δ = 149.8 (ipso-Mes), 141.8
(
2
3
ortho-Mes), 139.6 (para-Mes), 128.0 (meta-Mes), 26.2 (ortho-Me),
3
00, and a Bruker Avance 400 spectrometer. Elemental analyses were
+
1.0 (para-Me). ESI m/z (%): 360.2 (6.8) 359.2 (5.1) 358.2 (45.9)
performed at the microanalytical laboratories of the Universität Frank-
furt. Mass spectra were recorded with a Fisons VG Platform II instru-
ment. GC was performed with a Finnigan Trace GC with Trace MS
57.2 (21.0) 356.3 (100.0) 355.2 (58.5) 354.2 (77.5) 353.2 (52.5) 352.2
+
+
(30.9) [M] , calcd. for [M] 360.0 (5.8) 359.0 (4.2) 358.0 (43.4) 357.0
(20.3) 356.0 (100.0) 355.0 (54.2) 354.2 (77.5) 353.0 (45.6) 352.0
(25.6).
2
000 series. An UV lamp of the type TQ 150 Z2 has been used for
the photochemical experiments.
X-ray Crystallographic Study: Data Collection: Stoe-IPDS-II dif-
M[Mes]
was suspended in thf (10 mL). After adding of mesityllithium
0.020 g, 0.16 mmol) at room temperature, the reaction mixture was
stirred for 10 h. All volatiles were removed from the yellow solution
in vacuo and the residue was extracted with benzene (10 mL). The
extract was filtered through a frit. Slow concentration of the filtrate
2 2
: MCl [0.015 g 0.08 mmol (Cd), 0.022 g, 0.08 mmol (Hg)]
[19]
fractometer, empirical absorption correction using MULABS, struc-
[
20]
ture solution by direct methods,
structure refinement: full-matrix
(
2
[21]
least-squares on F with SHELXL-97. Hydrogen atoms were placed
on ideal positions and refined with fixed isotropic displacement param-
eters using a riding model. CCDC-806453 (Cd[Mes]
2
), CCDC-806452
) contain the
(
Hg[Mes] ), and CCDC-808674 (Hg[Mes]Cl·0.5HgCl
2
2
2
led to the deposition of X-ray quality crystals of M[Mes] at ambient
temperature.
supplementary crystallographic data for this paper. These data can be
obtained free of charge from The Cambridge Crystallographic Data
Centre via www.ccdc.cam.ac.uk/data_request/cif.
Cd[Mes]
300.0 MHz, CDCl
Me), 2.29 (s, 3 H, para-Me). C{ H} NMR (75.5 MHz, CDCl
55.7 (ipso-Mes), 145.0 (ortho-Mes), 138.1 (para-Mes), 126.4 (meta-
2
:
Yield: 0.017 g (68 %). M.p.: >250 °C. 1H NMR
): δ = 6.92 (s, 4 H, meta-Ph), 2.51 (s, 6 H, ortho-
(
3
1
3
1
Crystal data and structure refinement for Cd[Mes]
Mo-K , λ = 0.71073 Å, 4691 no. of reflections collected, 1377 no. of
independent reflections. R = 0.0542, wR = 0.1355 [I > 2σ(I)]. R
.0803, wR = 0.1482 (all data). Monoclinic crystal system, space
group P2
2
: T = 173(2) K,
3
): δ =
α
1
+
1
2
1
=
Mes), 27.7 (ortho-Me), 21.1 (para-Me). ESI m/z (%): 355.9 (4.5)
54.9 (72.9) 354.0 (21.9) 352.9 (100) 351.8 (40.0) 351.0 (85.7) 350.0
32.0) 349.1 (57.4) [M + 1] , calcd. for [M + 1] 356.1 (4.7) 355.1
25.3) 354.1 (18.7) 353.1 (100) 352.1 (54.5) 351.1 (85.1) 350.1 (48.3)
0
2
3
(
(
+
+
1
/n, Z = 2, a = 4.7083(9) Å, b = 10.9914(12) Å, c =
3
15.160(3) Å, β = 98.236(14)°, V = 776.5(2) Å .
3
49.1 (39.6).
Crystal data and structure refinement for Hg[Mes]
, λ = 0.71073 Å, 12721 no. of reflections collected, 1442 no. of
independent reflections. R = 0.0307, wR = 0.0726 [I > 2σ(I)]. R
.0451, wR = 0.0801 (all data). Monoclinic crystal system, space
group P2
2
: T = 173(2) K, Mo-
K
α
Hg[Mes]
5
2
: Yield: 0.026 g (75 %). C18
H
22Hg (438.96): C, 49.25, H,
): δ =
1
1
2
1
=
.05, Found C, 49.13, H, 5.16 %. H NMR (400.1 MHz, CDCl
3
0
2
7
.02 (s, 4 H, meta-Ph), 2.52 (s, 12 H, ortho-Me), 2.31 (s, 6 H, para-
1
3
1
1
/n, Z = 2, a = 4.8394(4) Å, b = 10.6515(7) Å, c =
Me). C{ H} NMR (75.5 MHz, CDCl
3
): δ = 169.8 (ipso-Mes), 144.4
3
1
5.1239(14) Å, β = 97.501(7)°, V = 772.92(11) Å .
(
2
ortho-Mes), 137.9 (para-Mes), 128.1 (meta-Mes), 24.4 (ortho-Me),
1
99
[18]
1.9 (para-Me). Hg NMR: see ref.
Crystal data and structure refinement for Hg[Mes]Cl·0.5HgCl
2
: T =
, λ = 0.71073 Å, 9981 no. of reflections collected,
080 no. of independent reflections. R = 0.0472, wR = 0.1102 [I >
σ(I)]. R = 0.0560, wR = 0.1148 (all data). Monoclinic crystal system,
1
2
2
73(2) K, Mo-K
α
Reaction of M[Mes]
charged with M[Mes]
2
3
(M = Cd, Hg) with BBr : A NMR tube was
[2 mg, 0.008 mmol (Cd); 6 mg, 0.014 mmol
D to which BBr [0.006 mL, 16 mg, 0.064 mmol
6 6 3
1
2
2
1
2
(
Hg)] in 1 mL C
space group P2
1
/n, Z = 2, a = 4.1064(4) Å, b = 17.1907(14) Å, c =
(Cd); 0.008 mL, 21 mg, 0.084 mmol (Hg)] was added. In both cases
3
1
5.969(2) Å, β = 95.799(9)°, V = 1121.5(2) Å .
the NMR spectra of the reaction solution revealed exclusively signals
that could be assigned to literature-known MesBBr
ditionally, a reddish precipitate formed in both cases.
[17]
2
3
and BBr . Ad-
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© 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 2011, 646–649

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