Engineering exceptionally strong oxygen superbases with 1, 8-diazanaphthalene di-N-oxides

Despotović, Ines; Vianello, Robert (2014) Engineering exceptionally strong oxygen superbases with 1, 8-diazanaphthalene di-N-oxides. Chemical communications, 50 (75). pp. 10941-10944. ISSN 1359-7345

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Abstract

DFT calculations revealed that 1, 8-diazanaphthalene di-N-oxides provide extraordinary oxygen superbases, whose gas-phase and acetonitrile basicities surpass those of classical naphthalene-based nitrogen proton sponges. Such high basicity is almost entirely a consequence of a large strain-induced destabilization in neutral forms, while only a small contribution is offered by the intramolecular [O–H...O]− hydrogen bonding upon protonation.

Item Type:	Article
Uncontrolled Keywords:	superbases
Subjects:	NATURAL SCIENCES > Chemistry NATURAL SCIENCES > Chemistry > Theoretical Chemistry NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Broensted and Lewis acids and bases in chemistry and biochemistry (Broenstedove i Lewisove kiseline i baze u kemiji i biokemiji)- Robert Vianello 098-0982933-2932 MZOS
Depositing User:	Robert Vianello
Date Deposited:	27 Jan 2016 13:11
URI:	http://fulir.irb.hr/id/eprint/2423
DOI:	10.1039/C4CC05125D

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