Inorganic Chemistry
ARTICLE
Chem. Soc. 2006, 128, 4210. (h) Ziatdinov, V. R.; Oxgaard, J.; Mironov, O. A.;
Young, K. J. H.; Goddard, W. A., III; Periana, R. A. J. Am. Chem. Soc.
2006, 128, 7404. (i) Davies, D. L.; Donald, S. M. A.; Macgregor, S. A.
J. Am. Chem. Soc. 2005, 127, 13754. (j) Gꢀomez, M.; Granell, J.; Martínez,
M. Organometallics 1997, 16, 2539. (k) Ryabov, A. D. Chem. Rev. 1990,
90, 403.
(28) (a) Crespo, M.; Martínez, M.; Sales, J. Organometallics 1992,
11, 1288. (b) Crespo, M.; Martínez, M.; Sales, J. Organometallics 1993,
12, 4297. (c) Crespo, M.; Martínez, M.; de Pablo, E. J. Chem. Soc., Dalton
Trans. 1997, 1231.
(29) Albert, J.; Granell, J.; Sales, J.; Solans, X.; Font-Altaba, M.
Organometallics 1986, 5, 2567.
(11) (a) Ackermann, L. Chem. Rev. 2011, 111, 1315. (b) Esteban, J.;
Martínez, M. Dalton Trans. 2011, 40, 2638. (c) Engle, K. M.; Wang,
D. H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 14137. (d) Favier, I.;
Gꢀomez, M.; Granell, J.; Martínez, M.; Font-Bardía, M.; Solans, X. Dalton
Trans. 2005, 123. (e) Gꢀomez, M.; Granell, J.; Martínez, M. Eur. J. Inorg.
Chem. 2000, 217. (f) Gꢀomez, M.; Granell, J.; Martínez, M. J. Chem. Soc.,
Dalton Trans. 1998, 37. (g) Estevan, F.; Gonzꢀalez, G.; Lahuerta, P.;
Martínez, M.; Peris, E.; van Eldik, R. J. Chem. Soc., Dalton Trans.
1996, 1045. (h) Gonzꢀalez, G.; Lahuerta, P.; Martínez, M.; Peris, E.;
Sanau, M. J. Chem. Soc., Dalton Trans. 1994, 545. (i) Estevan, F.;
Lahuerta, P.; Peris, E.; Ubeda, M. A.; Garcia-Granda, S.; Gꢀomez-Beltrꢀan,
F.; Pꢀerez-Carre~no, E.; Gonzꢀalez, G.; Martínez, M. Inorg. Chim. Acta 1994,
218, 189. (j) Garcia-Granda, S.; Lahuerta, P.; Latorre, J.; Martínez, M.;
Peris, E.; Sanau, M.; Ubeda., M. J. Chem. Soc., Dalton Trans. 1994, 539.
(12) Aullꢀon, G.; Chat, R.; Favier, I.; Font-Bardía, M.; Gꢀomez, M.;
Granell, J.; Martínez, M.; Solans, X. Dalton Trans 2009, 8292.
(13) Erlenmeyer, E. Ber. Dtsch. Chem. Ges. 1900, 33, 2036.
(14) (a) King, S. W.; Riordan, J. M.; Holt, E. M.; Stammer, C. H.
J. Org. Chem. 1982, 47, 3270. (b) Hamidian, H.; Tikdari, A. M.
Heterocycl. Commun. 2006, 12, 29.
(30) The reaction leading to [Pd(CH3CO2H)3(k1-Noxazolone)]2+
+
from [Pd(k2-CH3CO2)(CH3CO2H)(k1-Noxazolone)]+ + CH3CO2H2
has a calculated unfavorable energy of 12 kJ/mol in water, much less than
the accepted for the analogous [Pd(CH3CO2H)3(k1-Nimino)]2+ com-
plex (24 kJ/mol) in 12 M CH3CO2H.
(31) Liu, C. T.; Maxwell, C. I.; Edwards, D. R.; Neverov, A. A.;
Mosey, N. J.; Brown., R. S. J. Am. Chem. Soc. 2010, 132, 16599.
(32) (a) Aguilar, D.; Arag€uꢀes, M. A.; Bielsa, R.; Serrano, E.; Navarro,
R.; Urriolabeitia, E. P. Organometallics 2007, 26, 3541. (b) Bielsa, R.;
Navarro, R.; Lledꢀos, A.; Urriolabeitia, E. P. Inorg. Chem. 2007, 46, 10133.
(c) Aguilar, D.; Arag€uꢀes, M. A.; Bielsa, R.; Serrano, E.; Soler, T.; Navarro,
R.; Urriolabeitia, E. P. J. Organomet. Chem. 2008, 693, 417. (d) Aguilar,
D.; Bielsa, R.; Contel, M.; Lledꢀos, A.; Navarro, R.; Soler, T.; Urriolabeitia,
E. P. Organometallics 2008, 27, 2929.
(33) The reaction leading to [Pd(CF3CO2H)3(k1-Noxazolone)]2+
from [Pd(k2-CF3CO2)(CF3CO2H)(k1-Noxazolone)]+ + CF3CO2H2
+
has a calculated unfavorable energy of 6 kJ/mol in water, much less
than the accepted for the analogous acetic acid compound.
(34) Tjahjono, M.; Cheng, S.; Li, C.; Garland., M. J. Phys. Chem A.
2010, 114, 12168.
(15) (a) Yadav, L. D. S.; Singh, A. Tetrahedron Lett. 2003, 44, 5637.
(b) Ghosh, S.; Datta, D.; Sen, N. Synth. Commun. 1987, 17, 299. (c)
Bautista, F. M.; Campelo, J. M.; García, A.; Luna, D.; Marinas, J. M.;
Romero, A. A. J. Chem. Soc., Perkin Trans 2 2002, 227.
(16) (a) Rao, I. S.; Filler, R. Synthesis 1975, 12, 749. (b) Arenal, I.;
Bernabe, M.; Fernꢀandez-Alvarez, E. An. Quim., Serie C: Quim. Org. Bioquim.
1981, 77, 56. (c) Avenoza, A.; Busto, J. H.; Cativiela, C.; Peregrina, J. M.
Synthesis 1995, 671.
(17) Cleary, T.; Brice, J.; Kennedy, N.; Chavez, F. Tetrahedron Lett.
2010, 51, 625.
(18) (a) Butterick, J. R.; Unrau, A. M. Can. J. Chem. 1974, 52, 2873.
(b) Wong, H. N. C.; Xu, Z.; Le, C.; Hson, M.; Lee, C. M. Synthesis 1992,
8, 793.
(35) SAINT, version 5.0; Bruker Analytical X-ray Systems: Madison,
WI.
(36) CrysAlis RED, version 1.171.27p8; Oxford Diffraction Ltd.:
Oxford, U.K., 2005.
(37) Sheldrick, G. M. SADABS, Program for absorption and other
corrections; Go€ttingen University: G€ottingen, Germany, 1996.
(38) Sheldrick, G. M. SHELXS-86; Acta Crystallogr. 1990, A46, 467.
(39) Sheldrick, G. M. SHELXL-97: FORTRAN program for the
refinement of crystal structures from diffraction data; G€ottingen University:
G€ottingen, Germany, 1997. SHELXTL-PLUS, Release 5.05/V; Siemens
Analytical X-ray Instruments, Inc.: Madison, WI, 1996.
(40) Crespo, M.; Font-Bardía, M.; Granell, J.; Martínez, M.; Solans,
X. Dalton Trans. 2003, 3763.
(19) (a) Radadia, V. R.; Purohit, D. M.; Patolia, V. N. J. Inst. Chem.
2006, 78, 14. (b) See ref 5l.
(41) Bernhardt, P. V.; Gallego, C.; Martínez, M.; Parella, T. Inorg.
Chem. 2002, 41, 1747.
(20) (a) Bourotte, M.; Schmitt, M.; Follenius-Wund, A.; Pigault, C.;
Haiech, J.; Bourguignon, J. J. Tetrahedron Lett. 2004, 45, 6343. (b) see
reference 4b.
(21) Cativiela, C.; Díaz de Villegas, M. D.; Melꢀendez, E. J. Heterocycl.
Chem. 1985, 22, 1655.
(22) (a) Sen, B.; Ozturk, G.; Alp, S.; Aygun, M.; Buyukgungor, O.
Acta Crystallogr., Sect. C 2007, 63, o223. (b) Sun, Y.-F.; Cui, Y.-P. Acta
Crystallogr., Sect. E 2008, 64, o678.
(23) (a) Lazareva, A.; Daugulis, O. Org. Lett. 2006, 8, 5211. (b)
Fujiwara, Y.; Jia, C. Pure Appl. Chem. 2001, 73, 319. (c) See also refs 10j
and 11.
(24) (a) CRC Handbook of Chemistry and Physics, 55th ed.; Weast,
R. C., Ed.; CRC Press: Cleveland, OH, 1974. (b) Serjeant, E. P.;
Dempsey, B. Ionization Constants of Organic Acids in Aqueous Solution;
Pergamon: Oxford, 1979. (c) Namazian, M.; Zakery, M.; Noorbala,
M. R.; Coote, M. L. Chem. Phys. Lett. 2008, 451, 163.
(25) (a) Chen, L.-T.; Chen, G.-J.; Fu, X.-Y. Chin. J. Chem. 1995,
13, 487. (b) Ramsden, C. A.; Sargent, B. J.; Wallett, C. D. Tetrahedron
Lett. 1996, 37, 1901.
(26) (a) Tobe, M. L.; Burgess, J. Inorganic Reaction Mechanisms; Long-
man: Harlow, England, 1999. (b) Wilkins, R. G. Kinetics and Mechanisms
of Reactions of Transition Metal Complexes; VCH: Weinheim, Germany,
1991.
(27) (a) Gallego, C.; Gonzꢀalez, G.; Martínez, M.; Merbach, A. E.
Organometallics 2004, 23, 2434. (b) Bernhardt, P. V.; Bozogliꢀan, F.;
Macpherson, B. P.; Martínez, M.; Merbach, A. E.; Gonzꢀalez, G.; Sienra,
B. Inorg. Chem. 2004, 43, 7187.
(42) Binstead, R. A.; Zuberbuhler, A. D.; Jung, B. SPECFIT32,
[3.0.34; Spectrum Software Associates, 2005.
(43) (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.;
Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin,
K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.;
Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.;
Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa,
J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.;
Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.;
Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.;
Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.;
Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich,
S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.;
Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.;
Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.;
Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham,
M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.;
Johnson, B.; Chen, W.; Wong, M. W. Gonzꢀalez, C.; Pople, J. A. Gaussian
03, Revision D.01; Gaussian Inc.: Wallingford, CT, 2004. (b) Frisch,
M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.;
Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson,
G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov,
A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.;
Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda,
Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.;
Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.;
Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.;
8142
dx.doi.org/10.1021/ic200564d |Inorg. Chem. 2011, 50, 8132–8143