18962-96-4Relevant articles and documents
Reaction of bis(2,4-dinitrophenyl) phosphate with hydrazine and hydrogen peroxide. Comparison of O- and N- phosphorylation
Domingos, Josiel B.,Longhinotti, Elisane,Brandao, Tiago A. S.,Santos, Leonardo S.,Eberlin, Marcos N.,Bunton, Clifford A.,Nome, Faruk
, p. 7898 - 7905 (2004)
Nonionic hydrazine reacts with anionic bis(2,4-dinitrophenyl) phosphate (BDNPP), giving 2,4-dinitrophenyl hydrazine and dianionic 2,4-dinitrophenyl phosphate by an SN2(Ar) reaction, and at the phosphoryl center, giving 2,4-dinitrophenoxide ion and a transient phosphorylated hydrazine that rearranges intramolecularly to N-(2,4-dinitrophenyl)-N-phosphonohydrazine. Approximately 58% of the reaction at pD = 10 occurs by N-phosphorylation, as shown by 31P NMR spectroscopy. Reaction of HO2- is wholly at phosphorus, and the intermediate peroxophosphate reacts intramolecularly, displacing a second 2,4-dinitrophenoxide ion, or with H 2O2, giving 2,4-dinitrophenyl phosphate and O2. Rate constants of O- and N-phosphorylation in reactions at phosphorus of NH2-NH2, HO2-, and NH2OH and its methyl derivatives follow Broensted relationships with similar slopes, but plots differ for oxygen and nitrogen nucleophiles. The reaction with NH2NH2 has been probed by using both NMR spectroscopy and electrospray ionization mass and tandem mass spectrometry, with the novel interception of key reaction intermediates in the course of reaction.
Heterodinuclear Zn(II)?Fe(III) and Homodinuclear M(II)?M(II) [M?=?Zn and Ni] complexes of a Bicompartmental [N6O] ligand as synthetic mimics of the hydrolase family of enzymes
Pathak, Chandni,Kumar, Dharmendra,Gangwar, Manoj Kumar,Mhatre, Darshan,Roisnel, Thierry,Ghosh, Prasenjit
, p. 30 - 42 (2018)
Heterodinuclear mixed valence [Zn(II)?Fe(III)] and the homodinuclear [Zn(II)?Zn(II)] and [Ni(II)?Ni(II)] complexes of a bicompartmental ligand containing a bridging phenoxy as a O?donor and four pyridyl moieties and two amine moieties as the N?donors exhi
Reactions of bis(2,4-dinitrophenyl) phosphate with hydroxylamine
Domingos, Josiel B.,Longhinotti, Elisane,Bunton, Clifford A.,Nome, Faruk
, p. 7051 - 7058 (2007/10/03)
For dephosphorylation of bis(2,4-dinitrophenyl) phosphate (BDNPP) by hydroxylamine in water, pH region 4-12, the observed first-order rate constant, kobs, initially increases as a function of pH, but is pH-independent between pH 7.2 and pH 10. The initial BDNPP cleavage by nonionic NH 2OH (a short-lived O-phosphorylated hydroxylamine, 2, followed by three possible reactions: (1) reaction of 2 with hydroxylamine, generating 2,4-dinitrophenyl phosphate (DNPP, 3), which subsequently forms DNP; (2) intramolecular displacement of the second DNP group and rapid decomposition of the cyclic intermediate to form phosphonohydroxylamine and eventually inorganic phosphate; (3) a novel rearrangement with intramolecular aromatic nucleophilic substitution involving a cyclic intermediate and migration of the 2,4-dinitrophenyl group from O to N. Values of kobs increase modestly with pH > 10, the reaction is biphasic, and the yield of DNP increases. An increase in [NH2OH] also increases the yield of DNP, due largely to accelerated hydrolysis of DNPP.
