✦ LIBER ✦

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

✍ Scribed by J. R. Penton; H. Zollinger

Publisher: John Wiley and Sons
Year: 1971
Tongue: German
Weight: 423 KB
Volume: 54
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19710540217

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✦ Synopsis

Abstract

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 or BF) 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.

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