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The Rôle of Solvent Participation in Electrophilic Aromatic Substitution: Rates of a diazo coupling reaction in water and in aprotic polar solvents. 24th Communication on diazo coupling reactions
Author(s) -
Penton J. R.,
Zollinger H.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540217
Subject(s) - chemistry , diazo , nitromethane , electrophile , acetonitrile , solvent , solvent effects , medicinal chemistry , electrophilic aromatic substitution , photochemistry , polar , electrophilic substitution , organic chemistry , catalysis , physics , astronomy
The rates of the diazo coupling reaction of 4‐toluenediazonium salts with N, N‐dimethylaniline in tetramethylene sulfone, acetonitrile, water, and nitromethane at 30°C are the same within a factor of 5. No significant influence of ‘gegenions’ (HSO 4 ⊖or BF 4 ⊖ ) was found. The results are explained by postulating little solvent reorganisation in the transition state. They are discussed comparatively with solvent effects in other electrophilic aromatic substitutions, particularly with regard to the reactions of nitronium salts.