σ or π nucleophilic reactivity of imines?

DOI: 10.14469/hpc/2968 Metadata

Created: 2017-08-21 17:42

Last modified: 2017-08-21 17:47

Author: Henry Rzepa

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)

Description

Nucleophiles are species that seek to react with an electron deficient centre by donating a lone or a π-bond pair of electrons. The ambident variety has two or more such possible sources in the same molecule, an example of which might be hydroxylamine or H2NOH. I previously discussed how for this example, the energetics allow the nitrogen lone pair (Lp) to win out over the O Lp. Here, I play a similar game, but this time setting an NLp up against a π-pair.

Member of collection / collaboration

DOIDescription
10.14469/hpc/177 Computation data for Henry Rzepa's blog

Associated DOIs

Current dataset ...DOIDescription
References 10.14469/hpc/2969 σ or π? The ambident nucleophilic reactivity of imines: crystallographic and computational reality checks.
References 10.14469/hpc/2970 σ or π nucleophilic reactivity of imines? A mechanistic twist emerges.
References 10.14469/hpc/2971 σ or π nucleophilic reactivity of imines? A mechanistic reality check using substituents.

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