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Substituent effects in the gas‐phase pyrolysis of 4‐( N ‐arylamino)‐1‐butyl acetate and 5‐( N ‐arylamino)‐ 1‐pentyl acetate
Author(s) -
AlAwadi Nouria A.,
Elnagdi Mohamed H.,
Kaul Kamini,
Chuchani Gabriel
Publication year - 2000
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 - 10.1002/1099-1395(200011)13:11<675::aid-poc298>3.0.co;2-5
Subject(s) - chemistry , substituent , pyrolysis , decomposition , gas phase , medicinal chemistry , butyl acetate , organic chemistry , homogeneous , atmospheric temperature range , ethyl acetate , ion , physics , solvent , thermodynamics , meteorology
A kinetic study of the gas‐phase pyrolysis of 4‐ and 5‐( N ‐arylamino)‐1‐butyl and ‐1‐pentyl acetate was made. Each ester was pyrolysed at five or six different temperatures and over a temperature range not less than 50 °C. These reactions were homogeneous and unimolecular. The reactivities of these compounds were compared with those of the parent compounds 4‐ and 5‐( N ‐phenyl)‐1‐butyl and ‐1‐pentyl acetate and with each other. The products of the decomposition reaction of these compounds suggest an anchimeric assistance of the amino substituent for a trans elimination, indicating that an ion‐pair type of mechanism may be operating during the process of elimination. Copyright © 2000 John Wiley & Sons, Ltd.