ISSN:
0538-8066
Keywords:
Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Gas-phase elimination reactions of number of N-substituted diacetamides have been studied. The rates of N-phenyl, 4-methoxyphenyl, 4-nitrophenyl, and benzyl diacetamide have been measured between 643-683, 642-693, 673-725, and 555-610 K, respectively. They undergo unimolecular first-order elimination reactions, for which log A = 12.8, 12.9, 12.8, and 11.0 s-1 and Ea = 185.7, 191.4, 193.4, and 143.6 kJ mol-1, respectively. The reactivity of these compounds has been compared with the unsubstituted diacetamide at 600 K. The kinetic data reveals that each of the N-aryldiacetamides is less reactive than the parent molecule. We attribute this observation to the resonance of the lone pair of electrons on the nitrogen with either the two carbonyl oxygen atoms or with the 6π electrons in the aromatic ring which will result in the stabilization of the N-aryldiacetamides related to the parent molecules. © 1994 John Wiley & Sons, Inc.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/kin.550260909
