Ambident Reactivity of the Nitrite Ion Revisited | Zendy

Tishkov Alexander A. | Zendy; Schmidhammer Uli | Zendy; Roth Stefan | Zendy; Riedle Eberhard | Zendy; Mayr Herbert | Zendy

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Ambident Reactivity of the Nitrite Ion Revisited

Author(s) -

Tishkov Alexander A.,

Schmidhammer Uli,

Roth Stefan,

Riedle Eberhard,

Mayr Herbert

Publication year - 2005

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/anie.200501274

Subject(s) - carbocation , reactivity (psychology) , chemistry , rationalization (economics) , medicinal chemistry , ion , computational chemistry , organic chemistry , philosophy , epistemology , medicine , alternative medicine , pathology

Lost control: The rationalization of the ambident reactivity of NO 2 − by the change between charge control to orbital control has to be revised. S N 1‐type reactions of carbocations with NO 2 − give kinetically controlled product mixtures only when these reactions proceed without activation energy (diffusion control). Activation‐controlled S N 1 alkylations are reversible and lead to the thermodynamically more stable nitro compounds.

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