Synthesis of unstable carbides Ag2C2n (n = 3, 4) and characterization via crystallographic analysis of their double salts with silver(I) trifluoroacetate

Article abstract of DOI:10.1021/ja412095y

Two new silver(I) carbides, Ag₂C₆ and Ag ₂C₈, have been synthesized, and single-crystal X-ray analysis of their crystalline silver(I) trifluoroacetate complexes, Ag ₂C₆·8AgCF₃CO₂·6H ₂O, 4(Ag₂C₆)·16AgCF₃CO ₂·14.5DMSO, and 2.5(Ag₂C₈) ·10AgCF₃CO₂·10DMSO, provides detailed information on the influence of ligand disposition and orientation of the all-carbon anionic ligands in the construction of multidimensional supramolecular structures, which are consolidated by argentophilic and weak inter-/intramolecular interactions.

Full text of DOI:10.1021/ja412095y

Communication
pubs.acs.org/JACS
Synthesis of Unstable Carbides Ag2C2n (n = 3, 4) and Characterization
via Crystallographic Analysis of Their Double Salts with Silver(I)
Trifluoroacetate
Sam C. K. Hau and Thomas C. W. Mak*
Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, New
Territories, Hong Kong SAR, People’s Republic of China
S
* Supporting Information
a
Scheme 1. Synthesis of Silver(I) Double Salts 3 and 4
ABSTRACT: Two new silver(I) carbides, Ag2C6 and
Ag2C8, have been synthesized, and single-crystal X-ray
analysis of their crystalline silver(I) trifluoroacetate
complexes, Ag2C6·8AgCF3CO2·6H2O, 4(Ag2C6)·
16AgCF3CO2·14.5DMSO, and 2.5(Ag2C8)·10AgCF3CO2·
10DMSO, provides detailed information on the influence
of ligand disposition and orientation of the all-carbon
anionic ligands in the construction of multidimensional
supramolecular structures, which are consolidated by
argentophilic and weak inter-/intramolecular interactions.
a
n
Reagents and conditions: (a) BuLi, (EtO)CHO, Et2O, 0 °C; (b)
PCC, CH2Cl2; (c) CBr4, PPh3, CH2Cl2.
ver the past decade, transition metal complexes
containing the linear M−CC−(CC)n−CC−M
O
(n = 1, 2) moiety, in which each terminal metal center (M =
Re,1a Au,1b Fe,1c Ru,2 Os,3 Pt,4) is also coordinated by other
ligands, have aroused much interest in view of their potential
application as intriguing structure building blocks owing to
their unique linear structural property.1−4 Meanwhile, our
group has conducted a systematic investigation on the synthesis
and structural characterization of a series of Ag(I) multiple salts
containing silver carbide, Ag2C2n (n = 1, 2), as a component, in
which the all-carbon dianion ethynediide, C22−, is generally
capsulated inside a polyhedral Agm (m = 6−10) cage, whereas
1,3-butadiyne-1,4-diide, C42−, exhibits variable coordination
modes involving each terminal triple bond and a Agm (m = 3−
5) basket.5,6 Herein we report the first successful synthesis of
their unstable higher homologues, silver(I) 1,3,5-hexatriyne-1,6-
diide (Ag2C6, 1) and silver(I) 1,3,5,7-octatetrayne-1,8-diide
(Ag2C8, 2), together with the crystal structures of three
polymeric Ag(I) double salts, Ag2C6·8AgCF3CO2·6H2O (3),7
4(Ag2C6)·16AgCF3CO2·14.5DMSO (4),8 and 2.5(Ag2C8)·
10AgCF3CO2·10DMSO (5).9
position during storage. Attempts to measure its IR or Raman
spectra were unsuccessful due to its instability to heat and
mechanical shock.]
Orange block-like crystals of the double salt Ag2C6·
8AgCF3CO2·6H2O (3)7 were obtained from the crystallization
of crude 1 in a concentrated aqueous solution of AgCF3CO2
(Scheme 1). In the crystal structure of 3, the C62− ion is located
at an inversion center, each terminal C atom being capsulated
by a butterfly-shaped Ag4 basket via the μ4-η1,η1,η1,η1 mode
(Figure 1a). Exterior silver atom Ag5 is attached to the Ag4
aggregate through a pair of μ3-η1,η2 trifluoroacetate groups
(abbreviated as O1 O2 and O7 O8). The resulting barbell-like
̂
̂
[Ag5C6Ag5] aggregate exhibits quasi-C2h symmetry with a plane
passing through atoms Ag3, Ag4, Ag5, Ag3A, Ag4A, and Ag5A
(Figure 1b). The Ag···Ag distances within the Ag4 aggregate lie
in the range 2.833(14)−2.962(13) Å, suggesting the existence
of significant argentophilic interactions.15,16 Three independent
aqua ligands are attached to the Ag atoms via different
coordination modes (O1W coordinates to Ag3 and Ag4 via μ2
mode, while both O2W and O3W attach to Ag5 via μ1 mode).
As illustrated in Figure 2a, adjacent barbell units are
interconnected by two pairs of symmetry-related trifluoroace-
Preparation of TMS−CC−CC−CC−TMS (6)
according to literature procedures10−12 involved two key
reactions, Corey−Fuchs olefination13 and carbene rearrange-
ment reaction.12,14 Reaction of 6 with AgClO4 in a 1:2 molar
ratio in MeOH at 23 °C for 30 min produced an orange
precipitate containing Ag2C6 (1), which was filtered out and
washed with deionized water (Scheme 1). [Caution! This crude
orange Ag2C6 amorphous powder, being insoluble in polar or
nonpolar solvents, is more explosive in the dry state than its lower
homologues Ag2C2 and Ag2C4 and could only be stored in the wet
form for 1−2 days in a refrigerator at −10 °C. In addition, 1
gradually darkened in color, which indicated slow decom-
tate groups (O3 O4 and O3A O4A; O5 O6 and O5B O6B) to
̂
̂
̂
̂
produce an infinite silver−organic layer structure, which is
further stabilized by additional H-bonding between trifluor-
oacetate groups and aqua ligand O1W (O1W···O4A, 2.825(12)
Å; O1W···O6A, 2.836(12) Å).
Received: November 27, 2013
© XXXX American Chemical Society
A
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Journal of the American Chemical Society
Communication
Figure 1. (a) Coordination environment of the Ag(I) atoms in double
salt Ag2C6·8AgCF3CO2·6H2O (3). The argentophilic Ag···Ag
distances shown as thick rods lie in the range 2.70−3.40 Å, and the
H and F atoms are omitted for clarity. Silver atoms are drawn as
thermal ellipsoids (50% probability level) with atom labeling. (b)
Perspective view of the barbell-like [Ag5C6Ag5] aggregate with a
pseudo-mirror plane passing through atoms Ag3, Ag4, and Ag5 and
their symmetry equivalents. Color scheme: purple, Ag; orange, O;
broken lines, Ag−C bonds; the same color scheme for atoms and
bonds applies to all other figures.
Figure 3. Coordination environment of five independent [Ag4C6Ag3]
and [Ag4C6Ag4] aggregates in double salt 4(Ag2C6)·16AgCF3CO2·
14.5DMSO (4), showing notable π−π stacking interactions. The
argentophilic Ag···Ag distances shown as thick rods lie in the range
2.70−3.60 Å, and the H and F atoms are omitted for clarity. Silver
atoms are drawn as thermal ellipsoids (50% probability level) with
atom labeling. Turquoise broken lines indicate π−π stacking
interactions; henceforth the same representation will apply to other
figures.
and 2.13(2)−2.86(2) Å for σ, π, and mixed (σ,π) interactions,
respectively, according to the classification in our previous
studies.19 The lengths of the C−C triple and single bonds are in
the ranges 1.19(3)−1.30(3) and 1.34(3)−1.38(3) Å, respec-
tively, consistent with the corresponding values in our previous
20
2−
observation for those complexes containing C4 dianion.
In addition, the ladder-like silver double-chain structures are
further consolidated by offset π−π interactions between
Figure 2. Perspective view of the crystal packing in 3 along (a) the c-
axis and (b) the a-axis, showing notable H-bonds. Green broken lines
indicate H-bond interactions; henceforth the same representation will
apply to other crystal packing figures.
2−
proximal triple bonds of adjacent C6 dianions [bond
center−bond center distances (Å) in the range 3.60−4.00 Å:
C1C2···C4C5, 3.683(3); C1BC2B···C4BC5B,
3.683(3); C3C3B···C6C7, 3.826(3); C3C3B···C7B
C6B, 3.825(3); C4C5···C10C11, 3.808(4); C6C7···
C12C13, 3.759(3); C8C9···C14C15, 3.858(3); C10
C11···C16C17, 3.848(4); C12C13···C18C19,
3.714(3); C14C15···C20C21, 3.869(3); C18C19···
C24AC24, 3.650(3); C18AC19A···C24C24A,
3.825(4); C20C21···C23C22, 3.823(4); C20AC21A···
C23AC22A, 3.650(3)] (see Figure S4a). These distances are
comparable to similar offset face-to-face π−π interactions
between phenyl rings.21
In complex 4, the 15 independent co-crystallized DMSO
ligand molecules (O33 to O47, the last one exhibiting half site-
occupancy) attached to different Ag centers take variable μ1-η1,
μ2-η1,η1, and μ3-η1,η1,η1 coordination modes (see Figure S3).
Adjacent silver−organic chains are interconnected through
additional H-bonding between DMSO molecules and nearby
trifluoroacetate groups (C71B−H···F47, 2.875(23) Å) to
generate a Ag(I)−organic supramolecular layer (Figure 4a).
Cross-linkage of such layers by weak C−H···F bonds between
DMSO ligands and trifluoroacetate groups from adjacent layers
[C60D−H···F25, 2.781(30) Å; C69−H···F15D, 2.605(21) Å;
C68−H···F18D, 2.779(18) Å; C80E−H···F9, 2.672(42) Å]
yields a 3-D supramolecular network (Figure 4b).
Further association of neighboring silver−organic layers
through additional H-bonding involving the other two aqua
ligands and trifluoroacetate groups (O2A···O3WB, 2.743(15)
Å; O2WA···O7B, 2.790(14) Å) gives a 3-D supramolecular
network (Figure 2b).
Starting material 6 was first added to a concentrated
DMSO17 solution of AgCF3CO2, quickly yielding an orange
Ag2C6 precipitate, which gradually dissolved to form a deep red
clear solution (Scheme 1). Transparent, orange plates of the
double salt 4(Ag2C6)·16AgCF3CO2·14.5DMSO (4)8 gradually
crystallized through diffusion from atmospheric moisture into
this deep red solution. Complex 4 contains five crystallo-
2−
graphically independent C6 ions, two located at crystallo-
graphic inversion centers (Figure 3). Among the five
[Ag4C6Ag3] and [Ag4C6Ag4] aggregates, the eight independent
terminal ethynide moieties exhibit different coordination
modes: μ4-η1,η1,η1,η2 for C1C2, C8C9, and C10C11;
μ3-η1,η1,η1 for C4C5 and C20C21; μ4-η1,η1,η1,η1 for
C14C15 and C16C17; and μ4-η1,η1,η2,η2 for C22C23.
Besides this, such supramolecular synthons18 coalesce with
their adjacent units through argentophilic interactions, with
Ag···Ag bond distances ranging 2.746(3)−3.573(2) Å, com-
parable to those observed in a wide variety of silver double and
multiple salts,16 to yield a pair of symmetry-related infinite
silver chains (Type I and II), which point in opposite directions
(Figure S1). As a result, a 1-D distorted ladder-like silver
double-chain structure is generated (Figure S2).
TMS−CC−(CC)2−CC−TMS (7) is synthesized
according to a modified literature procedure (Scheme 2).12
Unfortunately, crude Ag2C8 (2) cannot be isolated in powder
form like 1 due to its high reactivity and explosive properties.
Reaction between 7 and AgCF3CO2 in DMSO produced crude
Ag2C8 as an orange precipitate, which was later dissolved to
give a deep red clear solution. Orange plate-like crystals of
double salt 2.5(Ag2C8)·10AgCF3CO2·10DMSO (5) gradually
2−
The Ag−C bond distances between the Ag caps and C8
dianions lie in the ranges 2.12(1)−2.15(2), 2.42(2)−2.45(2),
B
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Communication
C11C12···C19C20, 3.926(3) Å; C13C14···C20A
C19A, 3.825(3) Å; C15C16···C18AC17A, 3.772(3) Å;
C17C18···C16AC15A, 3.771(3) Å; C19C20···C14A
C13A, 3.825(3) Å; C20AC19A···C12AC11A, 3.926(3)
Å], which provide additional stability to the Ag(I) double-chain
structure (Figure S4b).
The 10 independent DMSO ligands chelated on the Ag chain
can be classified into three groups according to their
corresponding coordination modes: μ1-η1, O23; μ2-η1,η1, O21,
O22, O24, O26, O27, O29, and O30; and μ3-η1,η1,η1, O25 and
O28 (Figure S5). Adjacent Ag(I)−organic chains are
interconnected by additional H-bonds between DMSO ligands
and trifluoroacetate groups [C53C−H···F17, 2.666(12) Å;
C48−H···F15E, 2.661(13) Å; C59E−H···F24, 2.598(12) Å] to
yield a supramolecular layer structure (Figure S6). Further
cross-linking of such layer structures by weak C−H···F between
DMSO ligands and trifluoroacetate groups [C49A−H···F8B,
2.536(16) Å; C41D−H···F21C, 2.605(12) Å; C42D−H···
F27C, 2.619(12) Å] gives a 3-D supramolecular network
structure (Figure S7).
The Ag−CC (σ-type interaction) and CC−C angles in
3−5 lie in the ranges 160.3(2)−171.4(2)° and 173.6(2)−
179.4(2)°, respectively, which show larger deviation from
linearity (<10° in general) than those reported in other C6/C8-
bridged transition metal (Re,1a Au,1b Fe,1c Ru,2 Os,3 Pt4)
complexes that are mostly dinuclear, indicating the effect of
multinuclear Ag−ethynide interactions on the AgC2nAg (n = 3,
4) segments.
Figure 4. Perspective view of the crystal packing in 4, along (a) the c-
axis and (b) the a-axis, showing notable H-bonds. Violet broken lines
indicate weak C−H···F interactions; henceforth the same representa-
tion will apply to other crystal packing figures.
a
Scheme 2. Synthesis of Silver(I) Double Salt 5
a
Reagents: (a) (COCl)2, DMF; (b) (TMS)2C4, AlCl3, CH2Cl2 ;(c)
n
CBr4, PPh3, CH2Cl2; (d) BuLi, C6H14.
formed through water diffusion into a concentrated
AgCF3CO2/Ag2C8 solution in DMSO. The asymmetric unit
of 5 contains three independent [Ag4C8Ag4] aggregates (Figure
5), one occupying a site of symmetry 1, together with 10
Among complexes 3−5, the coordination mode of either
C6 or C8 retains the highest ligation number20 of 8,
2−
2−
consistent with those established for C2 and C42−, featuring
2−
the co-existence of Ag(I)−C σ- and π-type bonding. Such high-
nuclearity coordination mode is further stabilized by ionic as
well as argentophilic interactions. The internal ethynyl groups
in both C62− and C82− are found to have no interaction with the
Ag(I) ions. Notably, they gain stabilization via offset π−π
stacking between adjacent ethynyl groups, which is seldom
observed in polymeric coordination networks. The coordina-
tion modes of the trifluoroacetate groups vary from the
common μ2-η2 kind to the μ2-η1,η1, μ3-η1,η2, and μ4-η2,η2
varieties. The trifluoroacetate ligand generally plays two
important roles: either spanning an edge of the Agn basket to
consolidate the [AgnCC](n−1)+ cationic moiety, or bridging
adjacent Agn baskets to generate an infinite chain or layer
structure. Complexes 3−5 all contain solvated water or DMSO
molecules in their crystalline lattices. In these complexes,
regular or weak C−H···F hydrogen bonds confer enhanced
stability to a coordination chain/layer or connect the chains
into a higher-dimensional supramolecular structure.
In summary, the present study provides the first examples of
polymeric organosilver(I) frameworks assembled with the
linear multinuclear Ag(I)−polyynediide supramolecular syn-
thons Agn⊂CC−(CC)m−CC⊃Agn (m = 1, 2; n = 3, 4).
Seen in a different light, the new Ag(I) carbides Ag2C6 and
Ag2C8, despite their inherent instability, are potentially useful as
structure building units for the construction of new
coordination networks in combination with coinage-metal
ions, inorganic/organic anionic bridging anions, and ancillary
ligands.
Figure 5. Coordination environment of the Ag(I) atoms in double salt
2.5(Ag2C8)·10AgCF3CO2·10DMSO (5). The argentophilic Ag···Ag
distances shown as thick rods lie in the range 2.70−3.40 Å, and the H
and F atoms are omitted for clarity. Silver atoms are drawn as thermal
ellipsoids (50% probability level) with atom labeling.
independent trifluoroacetate groups and 10 DMSO ligands.
2−
The Ag−C bond distances between the Ag caps and C8
dianions are in the ranges 2.07(1)−2.11(1), 2.48(1)−2.53(1),
and 2.16(1)−2.87(2) Å for σ, π, and mixed (σ,π) interactions,
respectively. The lengths of the C−C triple and single bonds lie
in the ranges 1.19(1)−1.24(2) and 1.33(2)−1.40(2) Å,
respectively.
Such Ag4 caps and their adjacent symmetric-related segments
are fused to form a Ag15 aggregate through atom sharing, and
such Ag15 aggregates are further coalesced to generate an
2−
infinite Ag chain. The three C8 dianions further undergo
offset π−π interactions [C1C2···C8BC7B, 3.960(3) Å;
C3C4···C6BC5B, 3.891(3) Å; C5C6···C4BC3B,
3.891(3) Å; C5C6···C13C14, 4.058(3) Å; C7C8···
C2BC1B, 3.960(3) Å; C7C8···C15C16, 3.782(3) Å;
C
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Journal of the American Chemical Society
Communication
R1 = 0.0761, wR2 = 0.2052 for 4290 reflections [I > 2σ(I)]. IR (KBr):
1928, 2047, 2129 cm−1 (νCC, w).
ASSOCIATED CONTENT
* Supporting Information
Experimental details, additional figures, H NMR spectra, and
X-ray crystallographic data in CIF format. This material is
available free of charge via the Internet at http://pubs.acs.org.
■
S
(8) Crystal data for 4: C170H150Ag48F96O93S29, M = 11612.40,
1
triclinic, space group P1 (No. 2), a = 15.124(18) Å, b = 22.255(3) Å, c
̅
= 26.642(3) Å, α = 102.224(2)°, β = 97.582(2)°, γ = 108.848(2)°, V =
8097.3(16) Å3, Z = 1, T = 173 K, R1 = 0.1072, wR2 = 0.3001 for 29 018
reflections [I > 2σ(I)].
(9) Crystal data for 5: C60H60Ag15F30O30S10, M = 3769.73,
monoclinic, space group C2/c (No. 15), a = 58.133(4) Å, b =
11.814(9) Å, c = 39.378(3) Å, β = 129.787(10)°, V = 20782(3) Å3, Z
= 8, T = 173 K, R1 = 0.0803, wR2 = 0.2266 for 18 835 reflections [I >
2σ(I)].
AUTHOR INFORMATION
Corresponding Author
tcwmak@cuhk.edu.hk
■
Notes
(10) Anthony, J.; Boldi, A. M.; Rubin, Y.; Hobi, M.; Gramlich, V.;
Knobler, C. B.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 13.
(11) We are indebted to a reviewer for drawing our attention to an
alternative route that gives 6 in gram scale. See: Rubin, Y.; Lin, S. S.;
Knobler, C. B.; Anthony, J.; Boldi, A. M.; Diederich, F. J. Am. Chem.
Soc. 1991, 113, 6943.
(12) Eisler, S.; Slepkov, A. D.; Elliott, E.; Luu, T.; McDonald, R.;
Hegmann, F. A.; Tykwinski, R. R. J. Am. Chem. Soc. 2005, 127, 2666.
(13) Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769.
(14) Xu, G.-L.; Xi, B.; Updegraff, J. B.; Protasiewicz, J. D.; Ren, T.
Organometallics 2006, 25, 5213.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work is dedicated to the memory of Dr. Hson-Mou Chang
(1923−2000). We gratefully acknowledge financial support by
the Hong Kong Research Grants Council (GRF CUHK
402710) and the Wei Lun Foundation, and the award of a
Postdoctoral Research Fellowship to S.C.K.H. by The Chinese
University of Hong Kong.
(15) (a) Pyykko, P. Chem. Rev. 1988, 88, 563. (b) Pyykko, P. Chem.
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N.; Hampel, F.; Bhuvanesh, N.; Gladysz, J. A. Dalton Trans. 2010, 39,
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Che, C.-M.; Zhu, N.; Lee, S.-T. J. Am. Chem. Soc. 2004, 126, 4958.
(5) For reviews, see: (a) Mak, T. C. W.; Zhao, X.-L.; Wang, Q.-M.;
Guo, G.-C. Coord. Chem. Rev. 2007, 251, 2311. (b) Mak, T. C. W.;
Zhao, L. Chem. Asian J. 2007, 2, 456. (c) Mak, T. C. W.; Zhao, L.;
Zhao, X.-L. Supramolecular Assembly of Silver(I) Complexes with
Argentophilic and Silver···Carbon Interactions. In The Importance of
Pi-Interactions in Crystal EngineeringFrontiers in Crystal Engineering
III; Tiekink, E. R. T., Zukerman-Schpector, J., Eds.; Wiley: Chichester,
2012; Chap. 13, pp 323−366.
(6) (a) Zhao, X.-L.; Mak, T. C. W. Inorg. Chem. 2010, 49, 3676.
(b) Hu, T.; Zhao, L.; Mak, T. C. W. Organometallics 2012, 31, 7539.
(c) Hu, T.; Mak, T. C. W. Inorg. Chem. 2013, 52, 9066. (d) Hu, T.;
Mak, T. C. W. Cryst. Growth Des. 2013, 13, 4957.
(7) Crystal data for 3: C22H12Ag10F24O22, M = 2163.02, monoclinic,
space group P21/c (No. 14), a = 10.871(7) Å, b = 10.844(7) Å, c =
20.337(20) Å, β = 97.983(10)°, V = 2374.3(3) Å3, Z = 2, T = 173 K,
D
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