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Stabilities of some 2‐( para ‐substituted‐phenyl)‐4,4,5,5‐tetramethyl‐1,3‐dioxolanes relative to their conjugate dioxolenium ions, radicals and carbanions as determined by thermodynamics for hydride and electron transfer in solution
Author(s) -
Arnett Edward M.,
Flowers Robert A.,
Meekhof Alison E.,
Pourjavadi Ali,
Walek Stuart A.
Publication year - 1994
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610071204
Subject(s) - chemistry , carbanion , hydride , carbocation , conjugate , radical , ion , yield (engineering) , medicinal chemistry , photochemistry , inorganic chemistry , organic chemistry , hydrogen , mathematical analysis , mathematics , materials science , metallurgy
A calorimetric method is described for the determination of the hydride affinities, Δ H H −(R + ) of seven dioxolenium ions from the title compounds and also tropylium, trityl and 9‐phenyl xanthylium cations by hydride transfer to the carbocations from BH 3 CN − . Cyclic voltammetric methods yield free energies for reduction of the cations to the conjugate radicals and to the carbanions. The Δ H H −(R + ) values correlate well with the first reduction potentials of the cations.