Utilizing the Azaazulene Scaffolds in the Design of New Organic Superbases.

ABSTRACT: New neutral organic superbases with 1-azaazulene(s) as a molecular backbone are computationally designed, employing two basic substituents: dimethylaminocyclopropen-imines (CPI) and dimethylaminocyclopropeniminophosphazenes (CPI-P). Their proton affinities, gas basicities, and pK a values in acetonitrile are obtained using density functional theory. Azaazulenes substituted with CPI have a computed PA in the gas phase ranging between 272.9 and 306.8 kcal mol-1, with pK a values in acetonitrile between 28.8 and 36 units. The substitution with the CPI-P group resulted in even stronger superbases, with a PA from 296.5 to 335.2 kcal mol-1 and corresponding pK a values from 33.9 to 50 units. This exceptionally strong thermodynamic basicity is accompanied by very high kinetic basicity as well; co

SUBMITTER: Baric D 

PROVIDER: S-EPMC6751732 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature