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Aminolyses of 2,4-dinitrophenyl and 3,4-dinitrophenyl 2-furoates: Effect of ortho-substituent on reactivity and mechanism

Title
Aminolyses of 2,4-dinitrophenyl and 3,4-dinitrophenyl 2-furoates: Effect of ortho-substituent on reactivity and mechanism
Authors
Um I.-H.Akhtar K.
Ewha Authors
엄익환
SCOPUS Author ID
엄익환scopusscopus
Issue Date
2008
Journal Title
Bulletin of the Korean Chemical Society
ISSN
0253-2964JCR Link
Citation
vol. 29, no. 4, pp. 772 - 776
Indexed
SCI; SCIE; SCOPUS; KCI WOS scopus
Abstract
Second-order rate constants (kN) have been measured spectrophotometrically for reactions of 3,4-dintrophenyl 2-furoate (2) with a series of secondary alicyclic amines in 80 mol % H2O/20 mol % dimethyl sulfoxide (DMSO) at 25.0 °C. The Brønsted-type plot exhibits a downward curvature for the aminolysis of 2, which is similar to that reported for the corresponding reactions of 2,4-dintrophenyl 2-furoate (1). Substrate 2 is less reactive than 1 toward all the amines studied but the reactivity difference becomes smaller as the amine basicity increases. Dissection of the second-order rate constants into the microscopic rate constants has revealed that the reaction of 2 results in a smaller k2/k-1 ratio but slightly larger k1 value than that of 1. Steric hindrance has been suggested to be responsible for the smaller k1 value found for the reactions of 1, since the ortho-substituent of 1 would inhibit the attack of amines (i.e., the k1 process).
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자연과학대학 > 화학·나노과학전공 > Journal papers
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