4-Nitrophenyl diphenyl phosphinate

Substituted phenolate anions react with 4-nitrophenyl diphenyl-phosphinate in a quasi-symmetrical reaction so that the effective charges can be determined for both forming and breaking bonds from the two quantities and Peq without any special experiments made on the leaving group substituents. The transition structure for the reaction, which has a concerted mechanism, has ... 

A commonly observed form of curve is bell-shaped. Figure 3.6 compares the effect observed in the reaction of a single alpha nucleophile (Ox ) at several common electrophilic centers C=0 (PNPA, 4-nitrophenyl acetate), P=0 (PNPDDP, 4-nitrophenyl diphenyl phosphinate), and SO (PNPBS, 4-nitrophenyl diphenyl sulfonate). Each of these shows the characteristic bell-shaped plot however, the magnitude of the alpha effect covers a 10-fold range. 

Bunton, C.A., Foroudian, H.J., Gillitt, N.D., Whiddon, C.R. Reactions of p-nitrophenyl diphenyl phosphinate with fluoride and hydroxide ion in nonionic micelles kinetic salt effects. J. Colloid Interface Sci. 1999, 2i5(l), 64—71. 

X-Ray analy.ses have been performed on salts of diphenyl phosphoric, phenylphosphonic, and trichloromethylphosphonic acids " phosphorylated urea and thiourea derivatives phenyl[[ -acetyloxy(4-nitrophenyl)]methyl]phosphinic acid ... 

Tetrabutylammonium amino-acid salts have been coupled to amino-acid esters using bis(n-nitrophenyl)phenyl phosphonate and (5-nitropyridyl)diphenyl phosphinate. The heterocyclic phosphonate (219) is also an effective reagent for the activation of carboxylic acids which react with amino-acid esters in its presence to form peptides in good yield. ° ... 

Paraoxon, sarin, and soman inhibit AChE, BuChE, and CarbE almost to the same extent. DFP inhibits BuChE and CarbE to the same extent and 1,000-fold more than AChE. Diphenyl -nitrophenyl phosphinate inhibits CarbEs more than 1,000-fold that of the ChEs. This explains why bis-p-nitrophenylphosphate is a specific inhibitor of CarbEs. A problem for CarbE as a scavenger is that VX is a 10,000-fold better inhibitor of the ChEs, and that ecothiophate is... 

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