By Gould R.F. (ed.)
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The formula (VIII) used by LOHS , the concept "Acyl" is so well-known that its use can be considered established. "Acyl" includes many groups: for example the fluoride ion, a second phosphoryloxy radical, aryloxy groups or heterocyclic oxo-compounds. e. the simple model of Y as leaving groups, 40 Reactivity (3) (VIII) Y = "Acyl" does not suffice in all cases to explain insecticidal action. Examples of this type are DFP (Di-isopropyl jIuorophosphates) and paraoxon, or the insecticidal pyroesters TEPP and schradan.
Generally alkaline hydrolysis of the enol phosphates [549J proceeds exclusively with loss of the enol. e. the proton transfer is rate limiting: ~ O - /C 1CH, (C,HsO),PO-O \- W ~ - F\ (C,HsO),P-X + O=C~ (10) "C1I 3 On the basis of then kinetic data, it appears questionable whether a water molecule is involved as a nucleophile in the transition state. Aryl esters of the type H hydrolyze under P - 0 cleavage. Here also, mesomeric and inductive effects overlap. If the benzene ring is substituted with electronwithdrawing groups, then the rate of hydrolysis of the corresponding phosphoric acid esters follows a linear free-energy relationship of the Hammett type .
G. O-methyl O-ethyl O-propyl phosphate. g. phosphoro-ate: Key-word Phosphoro Functional groups other than alkoxy ate thio amid(e) fluorid(e) chlorid(e) etc. Ph os ph oro I ate Ithio amido chi oro fluoro Two or more groups of the same type are designated by the prefixes di, tri, and so on: Phosphoro thioate di In a similar manner the names for free acids are based, for instance, on the keyword phosphoro-ic acid: Phosphoro ic acid thio amid(e) etc. e. the phosphorylated compounds) (cf. p. ). A principal disadvantage of the IUPAC nomenclature, however, is more of a philological nature, for in languages other than English it is often impossible to form words with analogous syllables.
Analytical Methods in Oceanography by Gould R.F. (ed.)