7340-09-2Relevant articles and documents
The α-effect in micelles: Nucleophilic substitution reaction of p-nitrophenyl acetate with N-phenylbenzohydroxamate ion
Ghosh, Kallol K.,Vaidya, Jyoti,Satnami, Manmohan Lal
, p. 26 - 31 (2008/02/09)
Pseudo-first-order rate constants have been determined for the nucleophilic substitution reactions of p-nitrophenyl acetate with p-chlorophenoxide (4-ClC6H4O-) and N-phenylbenzohydroxamate (C6H5CON(C
Inorganic anionic oxygen-containing α-nucleophiles - Effective acyl group acceptors: Hydroxylamine ranks first among the α-nucleophile series
Simanenko,Popov,Prokop'eva,Karpichev,Savelova,Suprun,Bunton
, p. 1286 - 1298 (2007/10/03)
Comparative analysis of the nucleophilicity of inorganic oxygen-containing α-nucleophiles (hydroxylamine and ClO-, BrO--, HOO--, NH2O-, and F- ions) covering the pKa range from -2 to 13.81 toward 4-nitrophenyl esters (4-nitrophenyl acetate, 4-nitrophenyl p-toluenesulfonate, diethyl 4-nitrophenyl phosphate, ethyl 4-nitrophenyl ethylphosphonate, and 4-nitrophenyl dimethylcarbamate) in water at 25°C (ionic strength μ 1.0, KCl) was performed in terms of the extrathermodynamic Brosted relation. It was found for the first time that hydroxylamine anion ranks first among the series of α-nucleophiles. It is more reactive than HOO- ion with respect to 4-nitrophenyl acetate (by a factor of ~8), 4-nitrophenyl p-toluenesulfonate (by a factor of ~4) and 4-nitrophenyl dimethylcarbamate (by a factor of ~10). The nucleophilicities of HOO- and NH 2O- ions toward diethyl 4-nitrophenyl phosphate and ethyl 4-nitrophenyl ethylphosphonate are comparable. Taking into account that neutral hydroxylamine exhibits an anomalously high reactivity, as compared to not only common organic but also inorganic α-nucleophiles, it may be regarded as a unique α-nucleophile. Both neutral hydroxylamine and its anion as O-nucleophiles ensure high rates of acyl group transfer throughout a wide range of pH.
NAD(P)H and Acetyl-CoA Models: Part II - Reaction of Diphenylnitrosamine and Methylphenylnitrosamine with 1,1'-Diacetyl-1,1',4,4'-tetrahydro-4,4'-bipyridine
Juneja, T. R.,Gupta, R. L.,Swarnakumar, K. G.,Pathak, D. P.
, p. 193 - 195 (2007/10/02)
Diphenylnitrosamine (1a) and methylphenylnitrosamine (1b) have been treated with 1,1'-diacetyl-1,1',4,4'-tetrahydro-4,4'-bipyridine (DTB) to understand the pattern arising as a result of biomimetic transfer of hydride and acetyl cation from the reagent.A number of products have been isolated and characterized.The interesting feature of the reaction is the -N-N=O cleavage in 1 to give hydroxylamine derivative, O-acetylacetohydroxamic acid (5).