Big Chemical Encyclopedia

Chemical substances, components, reactions, process design ...

Articles Figures Tables About

Does Resonance Always Stabilize an Anion

The pKa of 1,3-cyclopentadiene is 15, making it more acidic than water, as well as more acidic than almost any other hydrocarbon. This unusual acidity is presumably due to resonance stabilization of the conjugate base, which can be drawn as a hybrid of five resonance contributors. [Pg.183]

5-Cycloheptatriene might be expected to be even more acidic, since seven resonance contributors can be drawn for its conjugate base. However, the fact that several resonance contributors can be drawn for a molecule does not necessarily guarantee that it will actually be resonance stabihzed (see also Chapter 12, Problem 9). [Pg.183]

Electrostatic potential map for cyclopentadienyl anion shows most negatively-charged regions (in red) and less negatively-charged regions (in blue). [Pg.183]

See other pages where Does Resonance Always Stabilize an Anion is mentioned: [Pg.173]    [Pg.183]    [Pg.169]    [Pg.257]    [Pg.262]    [Pg.173]    [Pg.183]    [Pg.169]    [Pg.257]    [Pg.262]    [Pg.569]    [Pg.7]   


SEARCH



Anion stabilization

Resonance stabilization

Resonance stabilized anion

Resonance-stabilized

© 2024 chempedia.info