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Polycyclic croissant-like organic compounds are powerful superbases in the gas phase and acetonitrile--a DFT study
Nena Peran1, Zvonimir B Maksić
1Quantum Organic Chemistry Group, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10 000 Zagreb, Croatia.
Abstract:
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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