ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
Based on analysis of recently reported measurements, it is suggested that, provided a sufficiently large set of specific rate measurements in a wide variety of solvent types is available, the negligible to moderate improvements in the correlations of other types of benzylic chlorides, which are gained by use of a benzylic chloride (in place of 1-adamantyl chloride) as the standard substrate, do not justify the development of new specialized scales of solvent ionizing power. A similar conclusion is reached concerning solvent ionizing power scales developed for use with benzylic p-nitrobenzoates. However, such scales could be helpful when specific rates of solvolysis in only a limited variety of solvents are available, e.g. when a change in mechanism severely limits the range of operation of one of the pathways. Contrary to a previous claim, variations in ion-pair return could be the cause of deviations from Grunwald-Winstein plots for solvolyses of benzhydryl chloride in fluorinated alcohol solvents; such effects could be coupled, at least in part, with variations in aromatic ring solvation.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610050602
