Synthesis and Basicity Studies of Quinolino[7,8-]quinoline Derivatives.

Quinolino[7,8-]quinoline is a superbasic compound, with a p in acetonitrile greater than that of 1,8-bis(dimethylaminonaphthalene) (DMAN), although its synthesis and the synthesis of its derivatives can be problematic. The use of halogen derivatives 4,9-dichloroquinolino[7,8-]quinoline () and 4,9-dibromoquinolino[7,8-]quinoline () as precursors has granted the formation of a range of substituted quinolinoquinolines. The basicity and other properties of quinolinoquinolines can be modified by the inclusion of suitable functionalities.

Carbon Atom as an Extremely Strong Nucleophilic and Electrophilic Center: Dendritic Allenes Are Powerful Organic Proton and Hydride Sponges.

Gas-phase proton affinities (PAs) and hydride affinities (HAs) of organic bases possessing an allene moiety and substituted with methyl, dimethylamino, cyano, and vinyl substituents were examined with the B3LYP/6-311+G(2df,p)//B3LYP/6-31G(d) model. It was shown that a number of superbases and hyperbases can be obtained, as well as the potent hydride sponges. Methyl or dimethylamino substituents increased the proton affinity of the parent molecule, and the cyano substituents increased its hydride affinity.