Canadian Journal of Chemistry p. 910 - 915 (1982)
Update date:2022-09-26
Topics:
Stone, John A.
Splinter, Dena E.
Kong, Soon Yau
Proton transfer equilibria (B1H(+) + B2 <-> B1 + B2H(+)) and NO(+) transfer equilibria (B1NO(+) + B2 <-> B1 + B2NO(+)) have been studied for the following bases B, benzene, toluene, o-, m-, and p-xylene.NO(+) transfer equilibria for fluoro- and chlorobenzene have also been studied.Pulsed electron beam, high-pressure ion source mass spectrometry has been used to obtain the equilibrium constant K and hence the free energy changes ΔG0 and from van't Hoff plots, ΔH0 and ΔS0.Entropy changes are in general much smaller for NO(+) transfer than for H(+) transfer but the magnitude of the changes in the proton affinity and NO(+) affinity of toluene caused by a fluorine substituent is about the same, even though the absolute value of the proton affinity is greater by a factor of 4.The position of the F substituent on toluene has a marked effect on proton affinity but no effect on NO(+) affinity.The latter appears to be responsive only to the inductive effect.
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