Diethyl 4-chlorophenyl phosphate

DFT calculations on the alcoholysis (MeO ) and thiolysis (MeS ) of three aryl diethyl phosphates 4-X-C6H40P(=0)(0Et)2 (X = Me, H, Cl) and of triethyl phosphate (TEP) in the gas phase and in solution showed that (i) the alcoholysis of diethyl 4-chlorophenyl phosphate proceeded through a concerted mechanism, while an associative mechanism was observed for its thiolysis reaction (ii) the reactivity of diethyl phenyl and diethyl 4-methylphenyl phosphates were similar and reacted via an associative mechanism with both MeO and MeS (iii) for TEP, the alcoholysis and thiolysis reactions proceeded by an associative mechanism and (iv) thiolysis of the four triesters was less favourable than alcoholysis in the gas phase and in solution." ... 

A mixed ester such as diethyl p-chlorophenyl phosphate is readily prepared by the dropwise addition of diethyl phos-phorochloridate to sodium p-chlorophenoxide.5... 

The residue Asp-301, which is hydrogen bonded to His-254, has been proposed to deprotonate the bridging hydroxide nucleophile.253 Mutation of His-245 to Ala or Asp reduces the rate of hydrolysis of paraoxon by 1-2 orders of magnitude. In contrast, the hydrolysis for the slower substrate diethyl p-chlorophenyl phosphate increases by from 2- to 33-fold.253 This suggests that for the more activated... 

Figure 5.5 The relationship between hydrolyzability and anticholinesterase activity for seven substituted diethyl phenyl phosphates, a, tetraethyl pyrophosphate b, paraoxon c, ortho analogue to paraoxon d, meta analogue to paraoxon e, o-chlo-rophenyl diethylphosphate f, p-chlorophenyl diethylphosphate g, phenyl phosphate. (Data from Aldridge and Davidson, 1952a, 1952b.)...

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

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