The kinetics of ion-molecule reactions of proton transfer from the mol
ecular ion of toluene to thiophene, acetophenone, benzaldehyde, and py
ridine molecules is studied. The transfer is shown to proceed via an i
ntermediate complex, whose formation is associated with overcoming the
activation barrier at the expense of internal and kinetic energies of
the primary ions. The analysis of the data obtained shows that the re
action rate constant increases exponentially with increasing proton af
finity for both aromatic compounds and aliphatic ketones and alcohols
studied previously.