Dodeka(ethylene)octamine

Heterocyclic superbases: retrospective and current trends

“…Let us present two examples as an illustration. Thus, a B3LYP/6-31G* ( * ) calculation for hypothetical dodeca(ethylene)octamine 76 (Scheme 24) with eight nitrogen electron pairs directed toward the cavity interior showed that this compound would have gas-phase proton affinity PA = 263.5 kcal/mol [92]. This is much greater than for proton sponge 11 (PA = 246.2 kcal/mol; this value has been proposed as the limit for superbasicity in the gas phase [93]).…”

Host‐Guest Complexes of Dodeka(ethylene)octamine: Prediction of Ion Selectivity by Quantum Chemical Calculations IX

“…The first who synthesized a proton sponge based on the tetrahedron, was Inazu and his team in 1999 ( 1 ) . More than ten years later, Michael Bühl suggested in 2011 a cube based amine cage dodeka(ethylene)octamine ( 2 ) as a super base, whereas the dodecahedron inspired structure ( 3 ) should also be possible (see Figure ). Calculated gas phase proton affinities suggest a basicity comparable with 2 .…”