Polycyclic croissant-like organic compounds are powerful superbases in the gas phase and acetonitrile--a DFT study.

Chem Commun (Camb)

Quantum Organic Chemistry Group, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10 000 Zagreb, Croatia.

Published: January 2011

A new type of the π-electron polycyclic organic superbases is proposed exhibiting very high proton affinities in the gas phase spanning the range from 280 to 323 kcal mol(-1) and the pK(a) up to 41.4 units in the MeCN solutions. Their salient feature is formation of the (H(+))-bridge upon protonation and a strong cationic resonance effect in the corresponding conjugate acids.

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Source
http://dx.doi.org/10.1039/c0cc03386cDOI Listing

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