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Unproductive sigma and pi complexes in the reaction of 2‐chloroquinoxaline with piperidine in dimethyl sulphoxide
Author(s) -
Nasielski J.,
Rypens C.
Publication year - 1994
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610071004
Subject(s) - chemistry , piperidine , nucleophile , sigma , medicinal chemistry , amine gas treating , atmospheric temperature range , pi , organic chemistry , thermodynamics , catalysis , biochemistry , physics , quantum mechanics
Abstract The rate of the reaction of 2‐chloroquinoxaline with piperidine in dimethyl sulphoxide was measured over a wide range of amine concentrations and at several temperatures. It was found that the order with respect to the nucleophile is close to 1 between 300 and 320 K, but is definitely less at lower and higher temperature. It is suggested that below 300 K an unreactive charge‐transfer complex is formed between the reactants which dissociates at higher temperatures, whereas at temperatures higher than 320 K an unproductive σ complex is formed, the concentration of which increases with increase in temperature.