Naslov
Engineering Exceptionally Strong Oxygen Superbases with 1, 8-Diazanaphthalene di-N-oxides

Autori
Despotović, Ines ; Vianello, Robert

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Book of Abstracts of ESOR 2015 / - , 2015

Skup
ESOR 2015 : European Symposium on Organic Reactivity

Mjesto i datum
Kiel, Njemačka, 30.08.2015. - 04.09.2015

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
superbases

Sažetak
For more than four decades, the design and synthesis of neutral organic superbases have attracted much attention1 because their unique characteristics allow deprotonation of a wide range of weak acids. Although usually weaker than their inorganic counterparts, uncharged organobases have become widely used standard reagents in organic synthesis. DFT calculations revealed that naphthalenes bearing two 1, 8-bis-substituted N–oxides provide extraordinary oxygen superbases, whose gas-phase and acetonitrile basicities surpass those of classical nitrogen proton sponges involving naphthalenes equally di-substituted with dimethylamino, guanidino, and phosphazeno groups. Such pronounced basicity is almost entirely a consequence of a large strain-induced destabilization in neutral bases, while only a small contribution is offered by the intramolecular [O–H·····O]– hydrogen bonding in conjugate acids.2 References: 1. Ishikawa, T. Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts ; Wiley: New York, 2009. 2. Despotović, I., Vianello, R. Chem. Commun. 2014, 50, 10941-10944.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA