Inorganic Chemistry
Article
(10) (a) Kurtikyan, T. S.; Ford, P. C. Hexacoordinate oxy-globin
models Fe(Por)(NH3)(O2) react with NO to form only the nitrato
analogs Fe(Por)(NH3)(η1-ONO2), even at ∼ 100 K. Chem. Commun.
2010, 46, 8570−8572. (b) Yokoyama, A.; Han, J. E.; Karlin, K. D.;
Nam, W. An isoelectronic NO dioxygenase reaction using a nonheme
iron(III)-peroxo complex and nitrosonium ion. Chem. Commun. 2014,
50, 1742−1744. (c) Skodje, K. M.; Williard, P. G.; Kim, E. Conversion
of {Fe(NO)2}10 dinitrosyl iron to nitrato iron(III) species by
molecular oxygen. Dalton Trans. 2012, 41, 7849−7851.
Park, Y. J.; Siegler, M. A.; Karlin, K. D.; Nam, W. Reactions of Co(III)-
nitrosyl complexes with superoxide and their mechanistic insight. J.
Am. Chem. Soc. 2015, 137, 4284−4287.
(18) Rhine, M. A.; Rodrigues, A. V.; Urbauer, R. J. B.; Urbauer, J. L.;
Stemmler, T. L.; Harrop, T. C. Proton induced reactivity of NO− to
form a {CoNO}8 complex. J. Am. Chem. Soc. 2014, 136, 12560−12563.
(19) Wolak, M.; Zahl, A.; Schneppensieper, T.; Stochel, G.; van
Eldik, R. Kinetics and mechanism of reversible binding of to the
reduced cobalamin B12r (Cob(II)alamin). J. Am. Chem. Soc. 2001, 123,
9780−9791.
(11) (a) Roncaroli, F.; Videla, M.; Slep, L. D.; Olabe, J. A. New
features in the redox coordination chemistry of metal nitrosyls{M−
NO+; M−NO•; M−NO−(HNO)}. Coord. Chem. Rev. 2007, 251,
1903−1930. (b) Maiti, D.; Lee, D. − H.; Narducci Sarjeant, A. A.; Pau,
M. Y. M.; Solomon, E. I.; Gaoutchenova, K.; Sundermeyer, J.; Karlin,
K. D. Reaction of a copper−dioxygen Complex with nitrogen
monoxide (•NO) leads to a copper(II)−peroxynitrite species. J. Am.
Chem. Soc. 2008, 130, 6700−6701. (c) Goodwin, J. A.; Coor, J. L.;
Kavanagh, D. F.; Sabbagh, M.; Howard, J. W.; Adamec, J. R.; Parmley,
D. J.; Tarsis, E. M.; Kurtikyan, T. S.; Hovhannisyan, A. A.; Desrochers,
P. J.; Standard, J. M. Catalytic dioxygen activation by (nitro)(meso-
tetrakis(2-N-methylpyridyl)porphyrinato)cobalt(III) cation derivatives
electrostatically immobilized in nafion films: An experimental and
DFT investigation. Inorg. Chem. 2008, 47, 7852−7862. (d) Kurtikyan,
T. S.; Eksuzyan, S. R.; Goodwin, J. A.; Hovhannisyan, G. S. Nitric
oxide interaction with oxy−coboglobin models containing trans-
pyridine ligand: two reaction pathways. Inorg. Chem. 2013, 52, 12046−
12056. (e) Herold, S.; Koppenol, W. H. Peroxynitritometal complexes.
Coord. Chem. Rev. 2005, 249, 499−506. (f) Subedi, H.; Brasch, N. E.
Mechanistic studies on the reaction of nitroxylcobalamin with
dioxygen: evidence for formation of a peroxynitritocob(III)alamin
intermediate. Inorg. Chem. 2013, 52, 11608−11617. (g) Saha, S.;
Ghosh, S.; Gogoi, K.; Deka, H.; Mondal, B.; Mondal, B. Reaction of a
cobalt(III)-peroxo complex and NO: Formation of a putative
peroxynitrite intermediate. Inorg. Chem. 2017, 56, 10932−10938.
(12) Cao, R.; Elrod, L. T.; Lehane, R. L.; Kim, E.; Karlin, K. D. A
peroxynitrite dicopper complex: Formation via Cu-NO and Cu-O2
intermediates and reactivity via O-O cleavage chemistry. J. Am. Chem.
Soc. 2016, 138, 16148−16158.
(20) Saha, S.; Gogoi, K.; Mondal, B.; Ghosh, S.; Deka, H.; Mondal, B.
Reaction of a nitrosyl complex of cobalt porphyrin with hydrogen
peroxide: putative formation of peroxynitrite intermediate. Inorg.
Chem. 2017, 56, 7781−7787.
(21) (a) Siegl, W. O. Metal ion activation of nitriles. Syntheses of 1,3-
bis(arylimino)isoindolines. J. Org. Chem. 1977, 42, 1872−1878.
(b) Siegl, W. O.; Ferris, F. C.; Mucci, P. A. A convenient synthesis
of 3- and 4-methylphthalonitrile. J. Org. Chem. 1977, 42, 3442−3443.
(c) Siegl, W. O. Metal-chelating 1,3-bis(2′-pyridylimino)isoindolines.
J. Heterocycl. Chem. 1981, 18, 1613−1618. (d) Hanson, K.; Roskop, L.;
Djurovich, P. I.; Zahariev, F.; Gordon, M. S.; Thompson, M. E. A
paradigm for blue- or red-shifted absorption of small molecules
depending on the site of π-extension. J. Am. Chem. Soc. 2010, 132,
16247−16255.
(22) (a) Kozhukh, J.; Lippard, S. J. Influence of tetraazamacrocyclic
ligands on the nitric oxide reactivity of their cobalt(II) complexes. J.
Am. Chem. Soc. 2012, 134, 11120−11123. (b) Franz, K. J.; Doerrer, L.
H.; Spingler, B.; Lippard, S. J. Pentacoordinate cobalt(III) thiolate and
nitrosyl tropocoronand compounds. Inorg. Chem. 2001, 40, 3774−
3780. (c) Scott, M. J.; Lippard, S. J. Coupling of carbon monoxide to
isocyanides and enones induced by alkyl Zr(IV) and Hf(IV)
tropocoronand complexes. J. Am. Chem. Soc. 1997, 119, 3411−3412.
(d) Villacorta, G. M.; Lippard, S. J. Tropocoronands: a versatile
macrocyclic ligand system for mononuclear and binuclear metal
complexes. Pure Appl. Chem. 1986, 58, 1474−1484. (e) Jaynes, B. S.;
Doerrer, L. H.; Liu, S.; Lippard, S. J. Synthesis, tuning of the
stereochemistry, and physical properties of cobalt(II) tropocoronand
complexes. Inorg. Chem. 1995, 34, 5735−5744.
(23) Enemark, J. H.; Feltham, R. D. Principles of structure, bonding,
and reactivity for metal nitrosyl complexes. Coord. Chem. Rev. 1974,
13, 339−406.
(24) Deka, H.; Ghosh, S.; Saha, S.; Gogoi, K.; Mondal, B. Effect of
ligand denticity on the nitric oxide reactivity of cobalt(II) complexes.
Dalton Trans. 2016, 45, 10979−10988.
(13) Park, G. Y.; Deepalatha, S.; Puiu, S. C.; Lee, D.-H.; Mondal, B.;
Narducci Sarjeant, A. A.; del Rio, D.; Pau, M. Y. M.; Solomon, E. I.;
Karlin, K. D. A peroxynitrite complex of copper: formation from a
copper-nitrosyl complex, transformation to nitrite and exogenous
phenol oxidative coupling or nitration. JBIC, J. Biol. Inorg. Chem. 2009,
14, 1301−1311.
(25) Thyagarajan, S.; Incarvito, C. D.; Rheingold, A. L.; Theopold, K.
H. In pursuit of a stable peroxynitrite complex-NOx (x = 1−3)
derivatives of Tp(t-Bu,Me)Co. Inorg. Chim. Acta 2003, 345, 333−339.
(26) (a) Richter-Addo, G. B.; Hodge, S. J.; Yi, G. B.; Khan, M. A.;
Ma, T.; Van Caemelbecke, E.; Guo, N.; Kadish, K. M. Synthesis,
characterization, and spectroelectrochemistry of cobalt porphyrins
containing axially bound nitric oxide. Inorg. Chem. 1996, 35, 6530−
6538. (b) Kini, A. D.; Washington, J.; Kubiak, C. P.; Morimoto, B. H.
Spectroelectrochemical characterization of substituted cobalt nitrosyl
porphyrins. Inorg. Chem. 1996, 35, 6904−6906.
(27) (a) Wang, C.-C.; Chang, H.-C.; lai, Y.-C.; Fang, H.; Li, C.-C.;
Hsu, H.-K.; Li, Z.-Y.; Lin, T.-S.; Kuo, T.-S.; Neese, F.; Ye, S.; Chiang,
Y.-W.; Tsai, M.-Li.; Liaw, W.-F.; Lee, W.-Z. A structurally characterized
nonheme cobalt-hydroperoxo complex derived from its superoxo
intermediate via hydrogen atom abstraction. J. Am. Chem. Soc. 2016,
138, 14186−14189. (b) Fielding, A. J.; Lipscomb, J. D.; Que, L., Jr.
Characterization of an O2 adduct of an active cobalt-substituted
extradiol-cleaving catechol dioxygenase. J. Am. Chem. Soc. 2012, 134,
796−799. (c) Huber, A.; Muller, L.; Elias, H.; Klement, R.; Valko, M.
Cobalt(II) complexes with substituted salen-type ligands and their
dioxygen affinity in N-N-dimethylformamide at various temperature.
Eur. J. Inorg. Chem. 2005, 8, 1459−1467. (d) Fritch, J. R.; Christoph,
G. G.; Schaefer, W. P. Crystal structure of μ-peroxo-bis-
[(ethylenediamine)(diethylenetriamine) cobalt(III)] perchlorate.
Inorg. Chem. 1973, 12, 2170−2175. (e) Schaefer, W. P.; Marsh, R.
(14) (a) Kalita, A.; Kumar, P.; Mondal, B. Reaction of a copper(II)−
nitrosyl complex with hydrogen peroxide: putative formation of a
copper(I)−peroxynitrite intermediate. Chem. Commun. 2012, 48,
4636−4638. (b) Kalita, A.; Deka, R. C.; Mondal, B. Reaction of a
copper(II)−nitrosyl complex with hydrogen peroxide: phenol ring
nitration through a putative peroxynitrite intermediate. Inorg. Chem.
2013, 52, 10897−10903.
(15) (a) Yokoyama, A.; Han, J. E.; Cho, J.; Kubo, M.; Ogura, T.;
Siegler, M. A.; Karlin, K. D.; Nam, W. Chromium(IV)−peroxo
complex formation and its nitric oxide dioxygenase reactivity. J. Am.
Chem. Soc. 2012, 134, 15269−15272. (b) Yokoyama, A.; Cho, K. − B.;
Karlin, K. D.; Nam, W. Reactions of a chromium(III)-superoxo
complex and nitric oxide that lead to the formation of chromium(IV)-
oxo and chromium(III)-nitrito complexes. J. Am. Chem. Soc. 2013, 135,
14900−14903.
(16) (a) Clarkson, S. G.; Basolo, F. Reactions of some cobalt nitrosyl
complexes with oxygen. J. Chem. Soc., Chem. Commun. 1972, 0, 670−
671. (b) Clarkson, S. G.; Basolo, F. Study of the reaction of some
cobalt nitrosyl complexes with oxygen. Inorg. Chem. 1973, 12, 1528−
1534.
(17) (a) Kumar, P.; Lee, Y.-M.; Hu, L.; Chen, J.; Park, J. Y.; Yao, J.;
Chen, H.; Karlin, K. D.; Nam, W. Factors that control the reactivity of
cobalt(III)−nitrosyl complexes in nitric oxide transfer and dioxygena-
tion reactions: a combined experimental and theoretical investigation.
J. Am. Chem. Soc. 2016, 138, 7753−7762. (b) Kumar, P.; Lee, Y.-M.;
G
Inorg. Chem. XXXX, XXX, XXX−XXX