Table 1.

Energies^a (kcal mol⁻¹) for Gas Phase Protonations of TPP and Ph₄TCHP. Cl⁻ was used as counterion in calculations of mono- and dications.

	TPP	Ph4TCHP	Ph4TCHPcorrb
ΔEp(1)	−10.5848	−23.0291	−20.6710
ΔEp(2)	−26.8487	−33.1956	−29.9947
ΔEp	−37.4335	−56.2247	−50.6657
[ΔEp(2)-ΔEp(1)]	−16.2639	−10.1665	−9.3237
ΔEst(1)	24.9494	16.4256	16.4256
ΔEst(2)	8.4672	6.8071	6.8071
[ΔEst(2)-ΔEst(1)]	−16.4822	−9.6185	−9.6185
ΔEintr(1)	−35.5342	−39.4547	−37.0966
ΔEintr(2)	−37.0966	−40.0027	−36.8018

^aAll energies shown are derived from the pure uncorrected electronic energies of the corresponding components (see Supporting Information for details);

^bEnergies in this column were corrected by the differences in the corresponding proton affinities of TCHP and P to account for the σ-donor effect of tetracyclohexenogroups in Ph₄TCHP.