Extended hydrogen bond network enabled superbases.
New superbases, those organic compounds whose basicities are greater than that of proton sponge, are suggested that involve extended hydrogen-bonding networks. Addition of aminoethyl and related groups to the 1,8-diaminonaphthalene framework provide second- and third-layer hydrogen bonding in the conjugate base. DFT computations predict these compounds to be 10-15 kcal mol(-1) more basic than the proton sponge.
Department of Chemistry, Trinity University, One Trinity Place, San Antonio, Texas 78212, USA. sbachrach@trinity.edu
Steven M
SM
Bachrach