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The Reaction Mechanism Between Tetraarylammonium Salts and Hydroxide
Author(s) -
Gjineci Nansi,
Aharonovich Sinai,
WilldorfCohen Sapir,
Dekel Dario R.,
Diesendruck Charles E.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000435
Subject(s) - chemistry , hydroxide , ammonium , ammonium hydroxide , reaction mechanism , ion exchange , mechanism (biology) , inorganic chemistry , ion , electron transfer , organic chemistry , catalysis , philosophy , epistemology
The mechanism of the reaction between tetraaryl ammonium salts and hydroxide is studied experimentally for different N,N ‐diaryl carbazolium salts. The N,N ‐diarylcarbazolium salts are designed, synthesized, characterized, and reacted with hydroxide under different conditions. The products of the reactions were directly characterized or isolated when possible and, using different substituents, the reaction mechanisms were compared. An unexpected H/D exchange observed in these salts helped to discard the classical S N Ar mechanisms, supporting instead a radical mechanism initiated by a single‐electron transfer from the hydroxide. By understanding the preferred reaction pathways, better quaternary ammonium salts can be designed to withstand aggressive alkaline environments, critical for many practical applications such as anion‐exchange membrane fuel cells.