Job/Unit: I20387
/KAP1
Date: 23-08-12 18:48:31
Pages: 7
M. M. Gutiérrez, J. A. Olabe, V. T. Amorebieta
FULL PAPER
f) M. Liuzzi, M. Talpaert-Borle, J. Biol. Chem. 1985, 260, 5252;
g) L. Liu, P. Taverna, C. M. Whitacre, S. Chatterjee, S. L. Ger-
son, Clin. Cancer Res. 1999, 5, 2908; h) P. Taverna, H. S.
Hwang, J. E. Schupp, T. Radivoyevitch, N. N. Session, D. A.
Zarling, T. J. Kinsella, J. Cancer Res. 2003, 63, 838; i) M. She,
I. Pan, L. Sun, S. C. Yeung, Leukemia 2003, 19, 595.
[16] J. A. Olabe, G. L. Estiú, Inorg. Chem. 2003, 42, 4873.
[17] The central 15N label is demonstrated by the analysis of the
fragmentation spectrum of N2O (cf. foot-note 32 in Ref.[7]).
[18] J. D. Schwane, M. T. Ashby, J. Am. Chem. Soc. 2002, 124, 6822.
[19] N. G. del V. Moreno, N. E. Katz, J. A. Olabe, P. J. Aymonino,
Inorg. Chim. Acta 1978, 35, 183.
[20] a) H. E. Toma, J. M. Malin, Inorg. Chem. 1973, 12, 1039; b)
H. E. Toma, J. M. Malin, Inorg. Chem. 1973, 12, 2080.
[21] R. G. Wilkins, Kinetics and Mechanisms of Reactions of Transi-
tion Metal Complexes, 2nd ed., VCH Verlag, Weinheim, Ger-
many, 1992.
[22] Our calculations focus on the structural characterization of the
stable species appearing along the reaction pathway, without
attempting a more complex (exhaustive) kinetic study, which
should include a more thorough consideration of environmen-
tal and thermodynamic contributions. In this context, the re-
sults with the IPCM model reveal numerical changes in the
values of the activation parameters (particularly enthalpies) by
using alternative localizations of water molecules hydrogen-
bonded to the hydrogen atoms of the NH2 group in
NH2OCH3. We are still searching for an adequate theoretical
tool for the computation of the specific solvent effects. The
structural results derived from the geometry optimization pro-
cess could also be influenced by these limitations, although the
gross geometrical features of the N2O intermediates have al-
ready been reported in ref.[16]
[1]
a) I. M. Wasser, S. de Vries, P. Moënne-Loccoz, I. Schröder,
K. D. Karlin, Chem. Rev. 2002, 102, 1201; b) J. N. Armor (Ed.),
Environmental Catalysis, ACS Symp. Ser., Volume 552, 1994.
a) J. A. Olabe, L. D. Slep in Comprehensive Coordination Chem-
istry II, From Biology to Nanotechnology (Eds.: J. A. Mc Clev-
erty, T. J. Meyer), Elsevier, Oxford, 2004, vol. 1, p. 603; b) J. A.
Olabe, Adv. Inorg. Chem. 2004, 55, 61; c) L. J. Ignarro (Ed.),
Nitric Oxide, Biology and Pathobiology, Academic Press, San
Diego, CA, 2000.
a) J. A. Olabe, Dalton Trans. 2008, 3633; b) F. Roncaroli, M.
Videla, L. D. Slep, J. A. Olabe, Coord. Chem. Rev. 2007, 251,
1903; c) A. R. Butler, I. L. Megson, Chem. Rev. 2002, 102,
1155.
a) N. E. Katz, M. A. Blesa, J. A. Olabe, P. J. Aymonino, J. In-
org. Nucl. Chem. 1980, 42, 581; b) I. Maciejowska, Z. Stasicka,
G. Stochel, R. van Eldik, J. Chem. Soc., Dalton Trans. 1999,
3643.
[2]
[3]
[4]
[5]
[6]
[7]
L. Dozsa, V. Kormos, M. T. Beck, Inorg. Chim. Acta 1984, 82,
69.
S. K. Wolfe, C. Andrade, J. H. Swinehart, Inorg. Chem. 1974,
13, 2567.
M. M. Gutiérrez, V. T. Amorebieta, G. L. Estiú, J. A. Olabe, J.
Am. Chem. Soc. 2002, 124, 10307.
[8] a) J. H. Swinehart, P. A. Rock, Inorg. Chem. 1966, 5, 573; b) J.
Masek, H. Wendt, Inorg. Chim. Acta 1969, 3, 455.
[9] a) P. A. Rock, J. H. Swinehart, Inorg. Chem. 1966, 5, 1078; b)
S. L. Quiroga, A. E. Almaraz, V. T. Amorebieta, L. L. Perissin-
otti, J. A. Olabe, Chem. Eur. J. 2011, 17, 4145.
[10] a) M. D. Johnson, R. G. Wilkins, Inorg. Chem. 1984, 23, 231;
b) K. Szacilowski, A. Wanat, A. Barbieri, E. Wasielewska, M.
Witko, G. Stochel, Z. Stasicka, New J. Chem. 2002, 26, 1495.
[11] K. Wieghardt, Adv. Inorg. Bioinorg. Mech. 1984, 3, 213.
[12] a) I. Choi, Y. Liu, Z. Wei, M. D. Ryan, Inorg. Chem. 1997,
36, 3113; b) G. Alluisetti, A. E. Almaraz, V. T. Amorebieta, F.
Doctorovich, J. A. Olabe, J. Am. Chem. Soc. 2004, 126, 13432;
c) M. M. Gutiérrez, G. B. Alluisetti, C. Gaviglio, F. Doctorov-
ich, J. A. Olabe, V. T. Amorebieta, Dalton Trans. 2009, 1187; d)
M. M. Gutiérrez, J. A. Olabe, V. T. Amorebieta, Inorg. Chem.
2011, 50, 8817.
[23] F. Roncaroli, M. E. Ruggiero, D. W. Franco, G. L. Estiu, J. A.
Olabe, Inorg. Chem. 2002, 41, 5760.
[24] The reported unreactivity of N,NЈ-dimethylhydroxylamine to-
ward addition in [Fe(CN)5NO]2– (ref.[13]) constitutes good evi-
dence on the proton-releasing requirements. Similar unreactiv-
ity occurs with 1,1-dimethylhydrazine, when binding through
the NMe2 group (ref.[7]).
[25] J. E. Leffler, A. A. Bothner, J. Am. Chem. Soc. 1951, 73, 5473.
[26] M. D. Carducci, M. R. Pressprich, P. Coppens, J. Am. Chem.
Soc. 1997, 119, 2669.
[27] M. E. Chacón Villalba, E. L. Varetti, P. J. Aymonino, Vib.
Spectrosc. 1997, 14, 275.
[13] M. M. Gutiérrez, G. B. Alluisetti, J. A. Olabe, V. T. Amorebi-
eta, Dalton Trans. 2008, 5025.
[14] M. Feelisch, J. S. Stamler (Eds.), Methods in Nitric Oxide Re-
search, John Wiley and Sons, Chichester, 1996.
[28] T. C. Bissot, R. W. Parry, D. H. Campbell, J. Am. Chem. Soc.
1957, 79, 796.
[15] a) D. Benoit, V. Chaplinski, R. Braslau, C. J. Hawker, J. Am.
Chem. Soc. 1999, 121, 3904; b) P. Marsal, M. Roche, P. Tordo,
P. Sainte Claire, J. Phys. Chem. A 1999, 103, 2899; c) D. K.
Kim, Y. W. Kim, K. H. Kim, J. Heterocycl. Chem. 1997, 34,
311; d) Z. Gdaniec, B. Ban, L. C. Sowers, G. V. Fazakerley, Eur.
J. Biochem. 1996, 242, 271; e) C. Buschfort, M. R. Muller, S.
Seeber, M. F. Rajewski, J. Thomale, Cancer Res. 1997, 57, 651;
[29] H. E. Toma, Inorg. Chim. Acta 1975, 15, 205.
[30] H. E. Toma, J. M. Malin, E. Giesbrecht, Inorg. Chem. 1973,
12, 2084.
[31] a) R. N. Boos, Anal. Chem. 1948, 20, 964; b) NIOSH Manual
of Analytical Methods, Method No. 3500, 4th ed., 1994.
Received: April 18, 2012
Published Online:
6
www.eurjic.org
© 0000 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Inorg. Chem. 0000, 0–0