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A computational study of proton affinities of sesqui- and sester-7-azabicyclo[2.2.1]heptanes

RHF/6-31G* calculations, followed by single point energy estimations at the B3LYP/6-31+G**//RHF/6-31G* level were employed in a systematic computational study to estimate gas- phase proton affinities (PA) of selected sesqui- and sester-7-azabicyclo [2.2.1]norbornanes. Our calculations indicate that the basicities of the bridging nitrogen atoms are affected by their incorporation into a bicyclo[2.2.1]heptane framework. Furthermore, proximity effects of intramolecular hydrogen bonding plays an important role to increase basicity of fused 7-azanorbornanes in those cases where there is possibility of nitrogen bound hydrogen to bind to a neighbouring heteroatom at the adjacent 7-norbornane position.

DFT; calculations; proton affinities

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