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Pyrone‐Like Structures as Novel Oxygen‐Based Organic Superbases
Author(s) -
Suárez Dimas,
Menéndez J. Angel,
Fuente Enrique,
MontesMorán Miguel A.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000403)39:7<1320::aid-anie1320>3.0.co;2-e
Subject(s) - protonation , naphthalene , oxygen , chemistry , ab initio , pyrone , oxygen atom , computational chemistry , ab initio quantum chemistry methods , proton , resonance (particle physics) , organic chemistry , molecule , ion , physics , particle physics , quantum mechanics
Ab initio calculations predict that pyrone‐like structures (see picture) have large thermodynamic basicities similar to those of the proton sponges, such as 1,8‐bis(dimethylamino)naphthalene. These compounds could, therefore, be novel types of oxygen‐based organic superbases and show a clear structure – activity relationship between their unusual basicity and the resonance stabilization achieved by their protonated forms.