ISSN:
0894-3230
Keywords:
equilibrium acidities
;
homolytic bond dissociation enthalpies
;
benzaldoximes
;
phenyl methyl ketoximes
;
Chemistry
;
Theoretical, Physical and Computational Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The equilibrium acidities in DMSO of nine p- and m-substituted benzaldoximes and eight p-substituted phenyl methyl ketoximes were measured. Estimates of the homolytic bond dissociation energies (BDEs) of the acidic O - H bonds in these compounds were made by combination of their pKHA values with the oxidation potentials of their conjugate bases, Eox(A-), using the equation BDE = 1.37pKHA + 23.06Eox(A-) + 73.3 kcal (1 kcal = 4.184 KJ). Plots of Eox(A-) vs pKHA for p-substituted benzaldoximes and p-substituted phenyl methyl ketoximes were linear with slopes near unity. Consequently, as required by the above equation, the BDEs estimated for the O - H bonds in these oximes were constant, being 88.3 ± 0.3 and 89.2 ± 0.4 kcal, respectively. © 1998 John Wiley & Sons, Ltd.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
