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Mechanisms of Diazo Coupling Reactions. Part XXX. N ‐Diazo coupling of p ‐chloroaniline in acetonitrile: Rate‐Limiting proton transfer
Author(s) -
Penton John R.,
Zollinger Heinrich
Publication year - 1981
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.19810640602
Subject(s) - diazo , chemistry , acetonitrile , catalysis , base (topology) , proton , tetrafluoroborate , limiting , amine gas treating , photochemistry , coupling (piping) , computational chemistry , medicinal chemistry , organic chemistry , ionic liquid , mathematical analysis , mathematics , mechanical engineering , physics , quantum mechanics , engineering
The N ‐diazo coupling of p ‐chloroaniline with p ‐chlorobenzenediazonium tetrafluoroborate in acetonitrile at 30° shows non‐linear base catalysis by water. The results are interpreted in terms of the S E 2 mechanism with rate‐limiting proton loss at low base concentration; it is postulated, moreover that the reaction proceeds via transition states in which varying degrees of H‐bonding from the amine and the intermediate ω‐complex to different water species influence the initial step and the base catalysis.