The Structure of an Allenylsodium Derivative—Competition between Carbanion Resonance Delocalization and Gegenion Charge Localization | Zendy

Schade Christian | Zendy; Schleyer Paul von Ragué | Zendy; Weiss Erwin | Zendy; Geissler Maren | Zendy

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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.

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