Reactivities of arylnitrenium ions with guanine derivatives and other nucleophiles

Article Abstract:

Some quality of guanine makes its reaction with nitrenium ions faster than would be expected, but reasons are not clear. The nitrenium ions and carcinogens, 4-aminobiphenyl and 2-aminofluorene, and some derivatives have been studied using laser flash photolysis to find direct kinetic information about the lifetime of the electrophiles in water and reactivities with added nucleophiles. The ions are metabolized to hydroxylamine esters that with N-O heterolysis produce arylnitrenium ions that react with DNA. They react at guanine residues especially.

Research, Analysis, Guanine, Carcinogens, Chemical reaction, Rate of, Chemical kinetics, Nitrogen compounds

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Reactions of benzyl methyl substituted-benzyl phosphites with tert-butyl hypochlorite: "balanced TS" validating reactivity/selectivity principle

Article Abstract:

Reactions with tert-butyl hypochlorite of a series of benzyl-methyl- substituted benzyl phosphites have been studied. Phosphates, alkyl chlorides, isobutene and benzyl chlorides resulted. Phosphates having a tert-butyl group fragmented yielding isobutene and another phosphate. Hammett correlations indicate a polar transition state (TS). Phosphonium chlorides were intermediates. These reactions illustrate the reactivity/selectivity principle: selectivities decrease as temperatures increase.

Reactivity (Chemistry), Cyclic compounds, Organophosphorus compounds, Organic phosphorus compounds, Organochlorine compounds, Organic chlorine compounds

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