Abstract:
The inorganic nitrosyl (NO+) complexes [Fe(CN) 5NO]2-, [Ru(bpy)2 (NO)Cl]2+, and [IrCl5(NO)]- are useful reagents for the nitrosation of a variety of organic compounds, ranging from amines to the relatively inert alkenes. Regarding [IrCl5(NO)]-, its high electrophilicity and inertness define it as a unique reagent and provide a powerful synthetic route for the isolation and stabilization of coordinated nitroso compounds that are unstable in free form, such as S-nitrosothiols and primary nitrosamines. Related to the high electrophilicity of [IrCl5(NO)]-, an unusual behavior is described for its PPh4+ salt in the solid state, showing an electronic distribution represented by Ir IV-NO• instead of IrIII-NO+ (as for the K+ and Na+ salts). © 2007 American Chemical Society.
Registro:
Documento: |
Artículo
|
Título: | Performing organic chemistry with inorganic compounds: Electrophilic reactivity of selected nitrosyl complexes |
Autor: | Doctorovich, F.; Di Salvo, F. |
Filiación: | Departamento de Química Inorgánica, Analítica Y Química Física, Pabellón II, C1428EHA Buenos Aires, Argentina
|
Palabras clave: | inorganic compound; nitroso derivative; organic compound; article; chemical structure; chemistry; X ray crystallography; Crystallography, X-Ray; Inorganic Chemicals; Models, Molecular; Nitroso Compounds; Organic Chemicals |
Año: | 2007
|
Volumen: | 40
|
Número: | 10
|
Página de inicio: | 985
|
Página de fin: | 993
|
DOI: |
http://dx.doi.org/10.1021/ar6000457 |
Título revista: | Accounts of Chemical Research
|
Título revista abreviado: | Acc. Chem. Res.
|
ISSN: | 00014842
|
CODEN: | ACHRE
|
CAS: | Inorganic Chemicals; Nitroso Compounds; Organic Chemicals
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00014842_v40_n10_p985_Doctorovich |
Referencias:
- Ignarro, L.J., Introduction and Overview (2000) Nitric Oxide: Biology and Pathology, pp. 3-22. , Ignarro, L. J, Ed, Academic Press: San Diego, CA, Chapter 1, pp
- Stamler, J.S., Singel, D.J., Loscalzo, J., Biochemistry of nitric oxide and its redox-activated forms (1898) Science, 258. , and references therein. 1992
- Hayton, T. W.; Legzdins, P.; Sharp, W. B. Coordination and Organometallic Chemistry of Metal-NO Complexes. Chem. Rev. 2002, 102, 935-991; Ford, P. C.; Lorkovic, I. M. Mechanistic Aspects of the Reactions of Nitric Oxide with Transition-Metal Complexes. Chem. Rev. 2002, 102, 993-1017; McCleverty, J.A., Reactions of nitric oxide coordinated to transition metals (1979) Chem. Rev, 79, pp. 53-82
- Richter-Addo, G.B., Legzdins, P., (1992) Metal Nitrosyls, , Oxford University Press: New York
- Doctorovich, F., Trápani, C., The reaction of pentacyanonitrosylferrate(II) with primary amines as a source of stabilized aliphatic diazonium ions: A new route to secondary amines (1999) Tetrahedron Lett, 40, pp. 4635-4638
- Doctorovich, F., Escola, N., Trápani, C., Estrin, D.A., Turjanski, A.G., González Lebrero, M.C., Stabilization of Aliphatic and Aromatic Diazonium Ions by Coordination: An Experimental and Theoretical Study (2000) Organometallics, 19, pp. 3810-3817
- Doctorovich, F., Granara, M., Di Salvo, F., The reaction of [Ru(bpy)2 (NO)CI]2+ and [Fe(CN)5NO] 2- with benzylamine: Coordinated nitrosyl as an oxidizing agent (2001) Transition Met. Chem, 26, pp. 505-509
- Di Salvo, F., Crespo, A., Estrin, D.A., Doctorovich, F., Reaction pathways of 2,2,2-trifluoroethylamine and n-butylamine with [Ru(bpy) 2(NO)CI]2+ (2002) Tetrahedron, 58, pp. 4237-4244
- Doctorovich, F., Di Salvo, F., Escola, N., Trápani, C., Shimon, L., Formation of Coordinated Nitrosamines by Reaction of K[IrCI5NO] with Primary Amines (2005) Organometallics, 24, pp. 4707-4709. , and references therein
- Bowden, W.L., Little, W.F., Meyer, T.J., Diazotization of aromatic amines by ruthenium nitrosyl complexes (1977) J. Am. Chem. Soc, 99, pp. 4340-4345
- Estrin, D.A., Baraldo, L.M., Slep, L.D., Barja, B.C., Olabe, J.A., Theoretical and Experimental Study of Medium Effects on the Structure and Spectroscopy of the [Fe(CN)5NO]2- Ion (1996) Inorg. Chem, 35, pp. 3897-3903
- Hamra, O.Y., Slep, L.D., Olabe, J.A., Estrin, D.A., Influence of Solvent Effects on the Basicity of Pentaammine(pyrazine)ruthenium(II) and Pentacyano(pyrazine)ruthenate(II) Ions: A Density Functional Study (1998) Inorg. Chem, 37, pp. 2033-2038
- Roncaroli, F., Olabe, J.A., The Reactions of Nitrosyl Complexes with Cysteine (2005) Inorg. Chem, 44, pp. 4719-4727
- E1/2 = +0.96 V vs Ag/AgCl in 1 M HCIO4; E1/2 = -0.33 V vs ferrocene in butyronitrile; KBr pellet: 2006 cm-1; CH3CN solution: 1953 cm -1.; Sieger, M., Sarkar, B., Záliš, S., Fiedler, J., Escola, N., Doctorovich, F., Olabe, J.A., Kaim, W., Establishing the NO oxidation state in complexes [Cl5(NO)M]n-, M = Ru or Ir, through experiments and DFT calculations (2004) J. Chem. Soc., Dalton Trans, 12, pp. 1797-1800
- Perissinotti, L. L.; Estrin, D. A.; Leitus, G.; Doctorovich, F. A Surprisingly Stable S-Nitrosothiol Complex. J. Am. Chem. Soc. 2006, 128, 2512-2513; Escola, N., Llebaría, A., Leitus, G., Doctorovich, F., Formation of Coordinated C-Nitroso Compounds by Reaction of K[IrCI5NO] with Alkenes (2006) Organometallics, 25, pp. 3799-3801
- Bottomley, J.F., Crystal and molecular structures of potassium pentachloro- and pentabromo-nitrosyliridate hydrate (1975) Dalton Trans, 23, pp. 2538-2541
- Di Salvo, F., Escola, N., Scherlis, D.A., Estrin, D.A., Bondía, C., Murgida, D., Ramallo López, J.M., Doctorovich, F., Electronic Perturbation in a Molecular Nanowire of [IrCl 5(NO)]- Units Chem. Eur. J, , published on the web as Early View, DOI: 10.1002/chem.200601761
- PPh4+: tetraphenylphosphonium; AsPh 4+: tetraphenylarsonium; Paul, P.K.C., Aromatic ring-aliphatic ring stacking in organic crystal structures (2002) Cryst. Eng, 5, pp. 3-8
- Ye, X., Li, Z.-H., Wang, W., Fan, K., Xu, W., Hua, Z., The parallel π-π stacking: A model study with MP2 and DFT methods (2004) Chem. Phys. Lett, 397, pp. 56-61
- Caulfield, J., Wishnok, J., Tannenbaum, S., Nitric oxide-induced deamination of cytosine and guanine in deoxynucleosides and oligonucleotides (1998) J. Biol. Chem, 273, pp. 12689-126895
- Mohrig, J.R., Keegstra, K., Alkyldiazonium cations. I. Direct observation of the 2,2,2-trifluoroethyldiazonium ion (1967) J. Am. Chem. Soc, 89, pp. 5492-5493
- Berner, D., McGarrity, J.F., Direct observation of the methyldiazonium ion in fluorosulfuric acid (1979) J. Am. Chem. Soc, 101, pp. 3135-3136
- Ho, J., Fishbein, J.C., Rate-Limiting Formation of Diazonium Ions in the Aqueous Decomposition of Primary Alkanediazoates (1994) J. Am. Chem. Soc, 116, pp. 6611-6621
- Finneman, J.I., Fishbein, J.C., Mechanisms of Decomposition of (Z)-2,2,2-Trifluoro-1-arylethanediazoates in Aqueous Media (1996) J. Am. Chem. Soc, 118, pp. 7134-7138
- Trapani, C., Escola, N., Doctorovich, F., Formation of n-Butyldiazoate by Reaction of [M(CN)5NO]2- (M = Fe, Ru, Os) with Lithium n-Butylamide (2002) Organometallics, 21, pp. 2021-2023
- Dózsa, L., Kormos, V., Beck, M.T., Kinetics of the reaction of pentacyanonitrosylferrate(II) with aliphatic amines (1984) Inorg. Chim. Acta, 82, pp. 69-74
- Butler, A.R., Glidewell, C., Reglinski, J., Waddon, A., The pentacyanonitrosylferrate ion. I: Reactions with various amines (1984) J. Chem. Res., Synop, 9, pp. 279-284
- Casado, J., Mosquera, M., Rodriguez Prieto, M.F., Vázquez Tato, J., Kinetics and mechanism of reactions between the nitroprusside ion and secondary amines (1985) Ber. Bunsenges. Phys. Chem, 89, pp. 735-743
- Beck, M.T., Kathó, A., Dózsa, L., Formation of heterocyclic amino acids in the reaction of α,δ- and α,ε-diamino acids with nitrosylpentacyanoiron(II) (1981) Inorg. Chim. Acta, 55, pp. L55-L56
- Marcus, Y., The properties of organic liquids that are relevant to their use as solvating solvents (1993) Chem. Soc. Rev, 6, pp. 409-416
- Doyle, M.P., Guy, J.K., Brown, K.C., Mahapatro, S.N., VanZyl, C.M., Pladziewicz, J.R., Outer-sphere one-electron reductions of arenediazonium salts (1987) J. Am. Chem. Soc, 109, pp. 1536-1540
- Finneman, J.I., Fishbein, J.C., Changes in Transition State Structure for Protonation of Aryldiazomethanes in Aqueous Solutions (1994) J. Org. Chem, 59, pp. 6251-6256
- Lee, J., Chen, L., West, A.H., Richter-Addo, G.B., Interactions of Organic Nitroso Compounds with Metals (2002) Chem. Rev, 102, pp. 1019-1066
- Gowenlock, B. G.; Richter-Addo, G. B. Preparations of C-Nitroso Compounds. Chem. Rev. 2004, 104, 3315-3340; Wilder Jr, P., Culberson, C.F., Youngblood, G.T., 1,2-Dihydro-endo- dicyclopentadiene (1959) J. Am. Chem. Soc, 81, pp. 655-658
- Meinwald, J., Meinwald, Y.C., Baker III, T.N., The Steric Course of Nitrosyl Halide Additions to Norbornene and Norbornadiene (1963) J. Am. Chem. Soc, 85, pp. 2513-2514
- Clamp, S., Connelly, N.G., Howard, J.A.K., Manners, I., Payne, J.D., Geiger, W.E., Synthesis and reactivity of binuclear cyclopentadienylrhodium nitrosyl cations, and the X-ray structure of [Rh2(μ-CO)(μ-NO) (η-C5Me5)2][PF6] (1984) J. Chem. Soc., Dalton Trans, 8, pp. 1659-1665
- Becker, P.N., Bergman, R.G., Reversible exchange of (η-5- cyclopentadienyl)(dinitrosoalkane)cobalt complexes with alkenes. Kinetic and spectroscopic evidence for cyclopentadienyldinitrosyl-cobalt as a reactive intermediate (1983) J. Am. Chem. Soc, 105, pp. 2985-2995. , and references therein
- Pilato, R. S.; McGettigan, C.; Geoffroy, G. L.; Rheingold, A. L.; Geib, S. J. tert-Butylnitroso complexes. Structural characterization of W(CO)5(N(O)Bu-tert) and [CpFe(CO)(PPhe3)(N(O)Bu-tert)] +. Organometallics 1990, 9, 312-317, and references therein; Sohl, C.D., Lee, J., Alguindigue, S.S., Khan, M.A., Richter-Addo, G.B., Synthesis and solid-state molecular structures of nitrosoalkane complexes of iron porphyrins containing methanol, pyridine, and 1-methylimidazole ligands (2004) J. Inorg. Biochem, 98, pp. 1238-1246
- Tasker, H.S., Jones, H.O., The action of mercaptans on acid chlorides. Part II. The acid chlorides of phosphorus, sulphur, and nitrogen (1909) J. Chem. Soc., Trans, 95, pp. 1910-1918
- Stamler, J.S., Jaraki, O., Osborne, J., Simon, D.I., Keaney, J., Vita, J., Singel, D., Loscalzo, J., Nitric Oxide Circulates in Mammalian Plasma Primarily as an S-Nitroso Adduct of Serum Albumin (1992) Proc. Natl. Acad. Sci. U.S.A, 89, pp. 7674-7677
- Perissinotti, L.; Turjanski, A.; Estrin, D.; Doctorovich, F. Transnitrosation of Nitrosothiols: Characterization of an Elusive Intermediate. J. Am. Chem. Soc. 2005, 127, 486-487; Morando, P.J., Borghi, E.B., Schteingart, L.M., Blesa, M.A., The reaction of cysteine with the pentacyanonitrosylferrate(2-) ion (1981) J. Chem. Soc., Dalton Trans, 2, pp. 435-440
- Ford, P. C.; Lorkovic, I. M. Mechanistic Aspects of the Reactions of Nitric Oxide with Transition-Metal Complexes. Chem. Rev. 2002, 102, 993-1018; Szacilowski, K., Wanat, A., Barbieri, A., Wasielewska, E., Witko, M., Stochel, G., Stasicka, Z., Reactions of the [Fe(CN)5NO]2- complex with biologically relevant thiols (2002) New J. Chem, 26, pp. 1495-1502
- Schwane, J.D., Ashby, M.T., FTIR Investigation of the Intermediates Formed in the Reaction of Nitroprusside and Thiolates (2002) J. Am. Chem. Soc, 124, pp. 6822-6823
- Bartberger, M.D., Houk, K.N., Powell, S.C., Mannion, J.D., Lo, K., Stamler, J.S., Toone, E.J., Theory, Spectroscopy, and Crystallographic Analysis of S-Nitrosothiols: Conformational Distribution Dictates Spectroscopic Behavior (2000) J. Am. Chem. Soc, 122, pp. 5889-5890
- Grossi, L., Montevecchi, P.C., Strazzari, G., S-Nitrosothiol and Disulfide Formation through Peroxynitrite-Promoted Oxidation of Thiols (2001) Eur. J. Org. Chem, pp. 131-135
- Szacilowski, K., Stasicka, Z., S-nitrosothiols: Materials, reactivity and mechanisms (2001) Prog. React. Kinet. Mech, 26, pp. 1-58
Citas:
---------- APA ----------
Doctorovich, F. & Di Salvo, F.
(2007)
. Performing organic chemistry with inorganic compounds: Electrophilic reactivity of selected nitrosyl complexes. Accounts of Chemical Research, 40(10), 985-993.
http://dx.doi.org/10.1021/ar6000457---------- CHICAGO ----------
Doctorovich, F., Di Salvo, F.
"Performing organic chemistry with inorganic compounds: Electrophilic reactivity of selected nitrosyl complexes"
. Accounts of Chemical Research 40, no. 10
(2007) : 985-993.
http://dx.doi.org/10.1021/ar6000457---------- MLA ----------
Doctorovich, F., Di Salvo, F.
"Performing organic chemistry with inorganic compounds: Electrophilic reactivity of selected nitrosyl complexes"
. Accounts of Chemical Research, vol. 40, no. 10, 2007, pp. 985-993.
http://dx.doi.org/10.1021/ar6000457---------- VANCOUVER ----------
Doctorovich, F., Di Salvo, F. Performing organic chemistry with inorganic compounds: Electrophilic reactivity of selected nitrosyl complexes. Acc. Chem. Res. 2007;40(10):985-993.
http://dx.doi.org/10.1021/ar6000457