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The Structure of an Allenylsodium Derivative—Competition between Carbanion Resonance Delocalization and Gegenion Charge Localization
Author(s) -
Schade Christian,
Schleyer Paul von Ragué,
Weiss Erwin,
Geissler Maren
Publication year - 1986
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198609021
Subject(s) - carbanion , delocalized electron , counterion , lithium (medication) , ion , resonance (particle physics) , charge (physics) , derivative (finance) , chemistry , computational chemistry , crystallography , stereochemistry , physics , organic chemistry , atomic physics , psychology , quantum mechanics , financial economics , economics , psychiatry
The great importance of the counterion in determining the structure of a carbanion is clearly revealed by both calculations performed for allenyl anions and the results of the X‐ray structure anlaysis of 1. Na ⊕ favors the allenyl structure A having a strongly localized charge; the free anion and the lithium salts, on the other hand, are better described by the resonance structures A ↔ B ↔ C . The different behavior of organolithium and organosodium compounds is due to the stronger interaction of the anion with the smaller Li ⊕ ion.