20039-94-5Relevant articles and documents
Conversion of {Fe(NO)2}10 dinitrosyl iron to nitrato iron(iii) species by molecular oxygen
Skodje, Kelsey M.,Williard, Paul G.,Kim, Eunsuk
, p. 7849 - 7851 (2012)
A new {Fe(NO)2}10 dinitrosyl iron complex possessing a 2,9-dimethyl-1,10-phenanthroline ligand has been prepared. This complex exhibits dioxygenase activity, converting NO to nitrate (NO3 -) anions. During the o
Chromium(IV)-peroxo complex formation and its nitric oxide dioxygenase reactivity
Yokoyama, Atsutoshi,Han, Jung Eun,Cho, Jaeheung,Kubo, Minoru,Ogura, Takashi,Siegler, Maxime A.,Karlin, Kenneth D.,Nam, Wonwoo
, p. 15269 - 15272 (2012)
The O2 and NO reactivity of a Cr(II) complex bearing a 12-membered tetraazamacrocyclic N-tetramethylated cyclam (TMC) ligand, [Cr II(12-TMC)(Cl)]+ (1), and the NO reactivity of its peroxo derivative, [CrIV(12-TM
Reactions of a chromium(III)-superoxo complex and nitric oxide that lead to the formation of chromium(IV)-oxo and chromium(III)-nitrito complexes
Yokoyama, Atsutoshi,Cho, Kyung-Bin,Karlin, Kenneth D.,Nam, Wonwoo
, p. 14900 - 14903 (2013)
The reaction of an end-on Cr(III)-superoxo complex bearing a 14-membered tetraazamacrocyclic TMC ligand, [CrIII(14-TMC)(O2)(Cl)] +, with nitric oxide (NO) resulted in the generation of a stable Cr(IV)-oxo species, [CrIV(14-TMC)(O)(Cl)]+, via the formation of a Cr(III)-peroxynitrite intermediate and homolytic O-O bond cleavage of the peroxynitrite ligand. Evidence for the latter comes from electron paramagnetic resonance spectroscopy, computational chemistry and the observation of phenol nitration chemistry. The Cr(IV)-oxo complex does not react with nitrogen dioxide (NO2), but reacts with NO to afford a Cr(III)-nitrito complex, [CrIII(14-TMC)(NO2)(Cl)] +. The Cr(IV)-oxo and Cr(III)-nitrito complexes were also characterized spectroscopically and/or structurally.
An isoelectronic NO dioxygenase reaction using a nonheme iron(iii)-peroxo complex and nitrosonium ion
Yokoyama, Atsutoshi,Han, Jung Eun,Karlin, Kenneth D.,Nam, Wonwoo
, p. 1742 - 1744 (2014)
Reaction of a nonheme iron(iii)-peroxo complex, [FeIII(14-TMC) (O2)]+, with NO+, a transformation which is essentially isoelectronic with that for nitric oxide dioxygenases [Fe(iii)(O2?-) +
Phenol nitration induced by an {Fe(NO)2}10 dinitrosyl iron complex
Tran, Nhut Giuc,Kalyvas, Harris,Skodje, Kelsey M.,Hayashi, Takahiro,Moenne-Loccoz, Pierre,Callan, Paige E.,Shearer, Jason,Kirschenbaum, Louis J.,Kim, Eunsuk
, p. 1184 - 1187 (2011)
Cellular dinitrosyl iron complexes (DNICs) have long been considered NO carriers. Although other physiological roles of DNICs have been postulated, their chemical functionality outside of NO transfer has not been demonstrated thus far. Here we report the unprecedented dioxygen reactivity of a N-bound {Fe(NO)2}10 DNIC, [Fe(TMEDA)(NO)2] (1). In the presence of O2, 1 becomes a nitrating agent that converts 2,4,-di-tert-butylphenol to 2,4-di-tert-butyl-6-nitrophenol via formation of a putative iron-peroxynitrite [Fe(TMEDA)(NO)(ONOO)] (2) that is stable below -80 C. Iron K-edge X-ray absorption spectroscopy on 2 supports a five-coordinated metal center with a bound peroxynitrite in a cyclic bidentate fashion. The peroxynitrite ligand of 2 readily decays at increased temperature or under illumination. These results suggest that DNICs could have multiple physiological or deleterious roles, including that of cellular nitrating agents.
A Six-Coordinate Peroxynitrite Low-Spin Iron(III) Porphyrinate Complex - The Product of the Reaction of Nitrogen Monoxide (·NO(g)) with a Ferric-Superoxide Species
Sharma, Savita K.,Schaefer, Andrew W.,Lim, Hyeongtaek,Matsumura, Hirotoshi,Mo?nne-Loccoz, Pierre,Hedman, Britt,Hodgson, Keith O.,Solomon, Edward I.,Karlin, Kenneth D.
, p. 17421 - 17430 (2017)
Peroxynitrite (-OON=O, PN) is a reactive nitrogen species (RNS) which can effect deleterious nitrative or oxidative (bio)chemistry. It may derive from reaction of superoxide anion (O2?-) with nitric oxide (·NO) and has bee
Dioxygenation Reaction of a Cobalt-Nitrosyl: Putative Formation of a Cobalt-Peroxynitrite via a {CoIII(NO)(O2-)} Intermediate
Gogoi, Kuldeep,Saha, Soumen,Mondal, Baishakhi,Deka, Hemanta,Ghosh, Somnath,Mondal, Biplab
, p. 14438 - 14445 (2017)
A cobalt-nitrosyl complex, [(BPI)Co(NO)(OAc)], 1 {BPI = 1,3-bis(2′-pyridylimino)isoindol} was prepared and characterized. Structural characterization revealed that the cobalt center has a distorted square pyramidal geometry with the NO group coordinated f
Bio-inspired nitrogen oxide (NOx) interconversion reactivities of synthetic heme Compound-I and Compound-II intermediates
Mondal, Pritam,Tolbert, Garrett B.,Wijeratne, Gayan B.
, (2021/11/11)
Dioxygen activating heme enzymes have long predicted to be powerhouses for nitrogen oxide interconversion, especially for nitric oxide (NO) oxidation which has far-reaching biological and/or environmental impacts. Lending credence, reactivity of NO with h
Electrochemical Nitration with Nitrite
Blum, Stephan P.,Nickel, Christean,Sch?ffer, Lukas,Karakaya, Tarik,Waldvogel, Siegfried R.
, p. 4936 - 4940 (2021/10/25)
Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve as versatile building blocks. This study represents the electrochemical aromatic nitration with NBu4NO2, which serves a dual role as supporting electrolyte and as a safe, readily available, and easy-to-handle nitro source. Stoichiometric amounts of 1,1,1-3,3,3-hexafluoroisopropan-2-ol (HFIP) in MeCN significantly increase the yield by solvent control. The reaction mechanism is based on electrochemical oxidation of nitrite to NO2, which initiates the nitration reaction in a divided electrolysis cell with inexpensive graphite electrodes. Overall, the reaction is demonstrated for 20 examples with yields of up to 88 %. Scalability is demonstrated by a 13-fold scale-up.