A new type of proton sponge: bisbenzylguanidine naphthalene (1) was synthesized experimentally and studied computationally. Investigation of 1 and its mono-protonated and bi-protonated forms shows the high proton affinity (PA). Fators contributing to the basicity of 1, including sterics and π electron delocalization, will be discussed. Additionally, the effects of tethering the guandines will be reported. Calculations of a ring-closed guanidine naphthalene suggest this may enforce planarity in the mono-protonated form (2+1H). The intramolecular proton shift in 2+1H is calculated to be pseudopericyclic. Experimental results will be reported.

Investigations of a bisbenzylguanidine proton sponge and a ring-closed guanidine proton sponge

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.