ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The pKBH+ values of the conjugate acids of N-phenylhydroxylamines change drastically when the pKBH+ values are determined in dimethyl sulfoxide (DMSO) rather than methanol. The Hammett ρ values change from -5·69 to -1·20 on going from methanol to DMSO for protonated N-phenylhydroxylamines, in contrast to a shift of -4·70 to -4·83 for protonated N-methylanilines in the same two solvents. This large change in susceptibility indicates that the species from which the proton departs is not the same for protonated N-phenylhydroxylamines in the two solvents. Experimental and computational evidence supports ionization of the H+ from the O atom for the protonated N-phenylhydroxylamines in DMSO.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610080708
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