Abstract
In connection with structure-activity studies of insecticidal methyl carbamoyloxime acetylcholinesterase inhibitors, a straightforward approach to estimating pKa values of a series of precursor oximes and thiohydroximates has been developed. The pKa values of oximes correlate well with the proton chemical shifts of the oximino proton (δOH) in dilute dimethyl sulfoxide-d6 solution. The relationship pKa=29.10 – 1.63δOH was developed from δOH and pKa data for 20 compounds available either from the literature or derived experimentally from half-neutralization potentials (ΔHNP). Using this relationship, pKa values of more than 200 hydroximino compounds were calculated. The relationship has been extended to also include phenols: pKa=28.15 – 1.55δOH – 3.96l(phenol), where l(phenol) is an indicator variable indicating application of the equation to either a phenol [l(phenol)=1] or an oxime [l(phenol)=0].
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