Naslov
Predicted high proton affinity of poly-2, 5-dihydropyrrolimines-the aromatic domino effect

Autori
Maksić, Zvonimir B. ; Glasovac, Zoran ; Despotović, Ines

Izvornik
Journal of Physical Organic Chemistry (0894-3230) 15 (2002), 8; 499-508

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
aromaticity; basicity; proton affinity; proton sponges; superbases

Sažetak
The basicity of a family of 2, 5-dihydropyrrolimines is examined by the Hartree-Fock model. It is found that these systems exhibit high proton affinity, which increases with the number of the five-membered rings present. The origin of the pronounced basicity is identified as the tandem or domino aromatic effect occurring in the conjugate acids. The aromatization is triggered by protonation and spread over whole systems via mobile  -electrons. Proton affinities as high as 300 kcal/mol or more can be achieved in the gas phase, if the aromatization is combined with the favourable substituent effects and with the intramolecular hydrogen bond corona effect.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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