The utility of 1, 5, 7-triazabicyclo4.4.0dec-5-ene (TBD) as a hydrogen bond acceptor in the design of novel superbasic guanidines – A computational study

摘要

New guanidine-derived superbases with TBD-functionalized alkyl side chains have been developed using a computational DFT approach. Exploiting the high hydrogen bond basicity of TBD allowed access to systems with strong charge-assisted intramolecular hydrogen bonds in the protonated state. The enhanced stability of such guanidines is mirrored in their gas-phase basicities, which cover the range from 1044−1168 kJ mol−1, depending on the number of alkyl side chains, the type of alkyl spacer and the hydrogen-bonding pattern.