∫
[C NC6H4OOH] (0.056 g, 0.38 mmol) was added to the solution
material, and with the Cambridge Crystallographic Data Centre
as supplementary publication with the CCDC reference number
693068. For crystallographic data in CIF or other electronic
format see DOI: 10.1039/b811482j
obtained. After stirring for 1 h, the solvent was removed on a
rotary evaporator and the white solid obtained was recrystallized
from THF/hexane at -15 ◦C. Yield: 0.059 g, 26%. Anal. Calcd
for C20H18AuF4NO3: C, 40.47; H, 3.06; N, 2.36. Found: C, 40.31;
-1
∫
=
H, 2.88; N, 2.28%. IR (cm /KBr): n(C N): 2210, n(C O): 1686.
Acknowledgements
-1
1
∫
=
IR (cm /(THF): n(C N): 2217, n(C O): 1724, 1706. H NMR
(THF-d8): 8.2 (d, J = 8.3 Hz, 2H), 7.9 (d, J = 8.3 Hz, 2H), 4.12
This work was sponsored by the D.G.I. (Project CTQ2005-
08729/BQU and INTECAT Consolider Ingenio-2010 (CSD2006-
0003) and the Junta de Castilla y Leo´n (Project VA012A08). C. C.
and C. D. thank the Ministerio de Ciencia y Tecnolog´ıa for a grant.
(t, J = 6.4 Hz, 2H), 1.50–1.25 (m, 8H), 0.91 (t, J = 7.02 Hz). 19
NMR (THF-d8): -118.2 (m, 2F), -158.0 (m, 2F).
F
∫
[Au(C6F4C6F4Br)(C NC6H4COOH)] (5)
References
To a solution of (C6F4BrC6F4Br) (0,55 mmol) in 35 mL of dry
diethyl ether was added drop wise a solution of LiBun in hexane
(0,35 mL, 0.56 mmol) at -78 ◦C. After stirring for one hour, solid
[AuCl(tht)] (0.176 g, 0.38 mmol) was added at -78 ◦C and the
reaction mixture was slowly brought to room temperature (3 h).
Then, a few drops of water were added and the solution was filtered
in air through anhydrous MgSO4. The solvent was removed on
a rotary evaporator and the white solid obtained was redissolved
1 (a) L. Malatesta, F. Bonati, in Isocyanide Complexes of Metals, John
Wiley, London, 1969; (b) D. Lentz, Angew. Chem., Int. Ed. Engl., 1994,
33, 1315–1331.
2 M. Tamm and F. E. Hahn, Coord. Chem. Rev., 1999, 182, 175–209.
3 M. Tanabiki, K. Tsuchiya, Y. Kumanomido, K. Matsubara, Y. Mo-
toyama and H. Nagashima, Organometallics, 2004, 23, 3976–3981.
4 Y. Ito, M. Sugimone and M. Murakami, J. Am. Chem. Soc., 1991, 113,
8899–8908.
5 Y. Sun, K. Ye, H. Zhang, J. Zhang, L. Zhao, B. Li, G. Yang, B. Yang,
Y. Wang, S.-W. Lai and C.-M. Che, Angew. Chem., Int. Ed., 2006, 45,
5610–5613.
6 A. Mayr and J. Guo, Inorg. Chem., 1999, 38, 921–928.
7 C. Bartolome´, M. Carrasco-Rando, S. Coco, C. Cordovilla, P. Espinet
∫
in 20 mL of THF and [C NC6H4OOH] (0.081 g, 0.55 mmol) was
added to the solution obtained. After stirring for 1 h at room
temperature, the solution was reduced to 10 mL under reduced
pressure. Addition of 20 mL of hexane gave the product as a white
solid. Yield: 0.217 g, 55%. Anal. Calcd. for C20H5AuBrF8NO2;
C, 33.34; H, 0.70; N, 1.95. Found: C, 33.64; H, 1.24; N, 2.04%.
´
and J. Mart´ın-Alvarez, Organometallics, 2006, 25, 2700–2703.
8 V. Sharma and D. Piwnica-Worms, Chem. Rev., 1999, 99, 2545–2560.
9 (a) R. A. Michelin, M. F. C. Guedes da Silva and A. J. L. Pombeiro,
Coord. Chem. Rev., 2001, 218, 75–112; (b) W. P. Fehlhammer and M.
Fritz, Chem. Rev., 1993, 93, 1243–1280.
-1
-1
∫
=
=
IR (cm /KBr): n(C N): 2208, n(C O): 1701. IR (cm /(THF):
1
∫
n(C N): 2221, n(C O): 1724. H NMR (THF-d8): 8.2 (d, J =
8.2 Hz 2H), 7.9 (d, J = 8.2 Hz, 2H). 19F NMR (THF-d8): -116.3
(m, 2F), -134.3 (m, 2F), -138.5 (m, 2F), -140.9 (m, 2F).
10 U. Plaia, H. Stolzenberg and W. P. Fehlhammer, J. Am. Chem. Soc.,
1985, 107, 2171–2172.
11 K. Bartel and W. P. Fehlhammer, Angew. Chem., Int. Ed. Engl., 1974,
13, 599–600.
12 G. Facchin, R. A. Michelin, M. Mozzon and A. Tassan, J. Organomet.
Chem., 2002, 662, 70–76.
13 M. Basato, F. Benetollo, G. Facchin, R. A. Michelin, M. Mozzon,
S. Pugliese, P. Sgarbossa, S. Mazzega Sbovata and A. Tassan,
J. Organomet. Chem., 2004, 689, 454–462.
∫
[(l-4,4¢-C6F4C6F4){AuC NC6H4COOH)}2] (6)
To
a
solution of [(m-4,4¢-C6F4C6F4){Au(tht)}2] (0.296 g,
∫
0,34 mmol) in 10 mL of dry THF was added (C NC6H4COOH)
(0.101 g, 0,68 mmol). After the solution was stirred for 15 min
at room temperature, the solvent was removed under vacuum.
The solid obtained was washed with hexane (3 ¥ 10 mL) and
dichloromethane (3 ¥ 10mL), and finally recrystallized from
THF/hexane to give a white solid. Yield: 0.255 g, 76.2% Anal.
14 G. Facchin, P. Uguagliati and R. A. Michelin, Organometallics, 1984,
3, 1818–1822.
15 Z.-L. Lu, A. Mayr and K.-K. Cheung, Inorg. Chim. Acta, 1999, 284,
205–214.
16 S. Wang, A. Mayr and K.-K. Cheung, J. Mater. Chem., 1998, 8, 1561–
1565.
17 D. Samuel, B. Weinraub and D. Ginsburg, J. Org. Chem., 1956, 21,
Calcd for C28H10Au2F8N2O4: C, 34.15; H, 1.02; N, 2.85. Found: C,
34.49; H, 1.22; N 3.48%. IR (cm /KBr): n(C N): 2206; n(C O):
1691. IR (cm /(THF): n(C N): 2221, n(C O): 1724. H NMR
(THF-d8): 10.8 (s, 1H), 8.20 (d, J = 8.55 Hz, 2H), 7.9 (d, J =
8.5 Hz, 2H). 19F NMR (THF-d8): -117.3 (m, 4F), -141.1 (m, 4F).
376–377.
-1
∫
=
18 S. Coco, E. Espinet, P. Espinet and I. Palape, Dalton Trans., 2007,
3267–3272.
-1
1
∫
=
19 (a) T. Kato and J. M. J. Fre´chet, J. Am. Chem. Soc., 1989, 111, 8533–
8534; (b) M.-J. Brienne, J. Gabard, J.-M. Lehn and I. Stibor, J. Chem.
Soc., Chem. Commun., 1989, 1868–1870; (c) K. Willis, D. J. Price, H.
Adams, G. Ungar and D. W. Bruce, J. Mater. Chem., 1995, 5, 2195–
2199; (d) C. M. Paleos and D. Tsiourvas, Liq. Cryst., 2001, 28, 1127–
1161; (e) D. W. Bruce, in Advances in Inorganic Chemistry, 2001, 52,
151–204; (f) M. Grunet, R. A. Howie, A. Kaeding and C. T. Imrie,
J. Mater. Chem., 1997, 7, 211–214; (g) J.-F. Eckert, U. Maciejezuk, D.
Guillon and J.-F. Nierengarten, Chem. Commun., 2001, 14, 1278–1279;
(h) F. Wu¨rthner, S. Yao, B. Heise and C. Tschierske, Chem. Commun.,
2001, 14, 2260–2261; (i) N. Mizoshita, H. Monobe, M. Inoue, M.
Ukon, T. Watanabe, Y. Shimizu, K. Hanabusa and T. Kato, Chem.
Commun., 2002, 15, 428–429; (j) G. Pickaert, L. Douce, R. Ziessel and
D. Guillon, Chem. Commun., 2002, 15, 1584–1585; (k) S. Jin, Y. Ma,
S. C. Zimmerman and S. Z. D. Cheng, Chem. Mater., 2004, 16, 2975–
2977; (l) T. Kajitana, S. Kohmoto, M. Yamamoto and K. Kishikawa,
Chem. Mater., 2004, 16, 2329–2331; (m) J. A. McCubbin, X. Tong, Y.
Zhao, V. Snieckus and R. P. Lemieux, Chem. Mater., 2005, 17, 2574–
2581; (n) J. Barbera´, L. Puig, P. Romero, J. L. Serrano and T. Sierra,
J. Am. Chem. Soc., 2006, 128, 4487–4492.
Hydrogen-bonded stilbazole complexes
The supramolecular complexes were all prepared from the pure
components. Exact stoichiometric molar amounts of the two
compounds were dissolved in dry THF at ambient temperature,
and the solvent was eliminated in vacuum.
Experimental procedure for X-ray crystallography
Crystals of [Au(C6F5)(CNC6H4COOH)] (3) were obtained by slow
evaporation of a THF/hexane solution of the complex. Crys-
tallographic data (excluding structure factors) for the structure
reported in this paper have been deposited as supplementary
This journal is
The Royal Society of Chemistry 2008
Dalton Trans., 2008, 6894–6900 | 6899
©