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Carbanion or Amide? First Charge Density Study of Parent 2‐Picolyllithium
Author(s) -
Ott Holger,
Pieper Ursula,
Leusser Dirk,
Flierler Ulrike,
Henn Julian,
Stalke Dietmar
Publication year - 2009
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.200806221
Subject(s) - deprotonation , electrophile , carbanion , chemistry , amide , charge density , reactivity (psychology) , nucleophile , ring (chemistry) , density functional theory , atom (system on chip) , charge (physics) , computational chemistry , crystallography , stereochemistry , medicinal chemistry , ion , organic chemistry , physics , catalysis , medicine , alternative medicine , pathology , quantum mechanics , computer science , embedded system
The negative charge originating from deprotonation of the methyl group is distributed over the 2‐picolyl ring. Bonding properties derived from the electron density distribution support the enamide character of picolyllithium (PicLi; the picture shows the deformation density of [2‐PicLi⋅PicH] 2 ), but electrophilic attack occurs at the deprotonated C atom. This reactivity is rationalized by the electrostatic potential, which guides electrophiles towards the nucleophilic C atom.