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Factors influencing S-O bond and C-O bond cleavages in the reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates with various nucleophilic reagents

Title
Factors influencing S-O bond and C-O bond cleavages in the reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates with various nucleophilic reagents
Authors
Um I.-H.Kim J.-J.Kim M.-J.Kwon D.-S.
Ewha Authors
권동숙엄익환
SCOPUS Author ID
권동숙scopusscopus; 엄익환scopusscopus
Issue Date
1996
Journal Title
Bulletin of the Korean Chemical Society
ISSN
0253-2964JCR Link
Citation
Bulletin of the Korean Chemical Society vol. 17, no. 4, pp. 353 - 357
Indexed
SCIE; SCOPUS; KCI scopus
Document Type
Article
Abstract
Second-order rate constants have been measured spectrophotometrically for the reaction of 2,4-dinitrophenyl X-substituted benzenesulfonates with Z-substituted phenoxides in absolute ethanol at 25.0± 0.1 °C. The nucleophilic substitution reaction gives both S-O bond and C-O bond cleavage products. The extent of S-O bond cleavage increases significantly with increasing electron withdrawing ability of the sulfonyl substitutent X, while that of the C-O bond cleavage is independent on the electronic effect of the substituent. On the contratry, the effect of the substituent Z in the nucleophilic phenoxide is more significant for the C-O bond cleavage than for the S-O bond cleavage. Aminolyses of 2,4-dinitrophenyl benzenesulfonate (1) with various 1°, 2° and 3° amines have revealed that steric effect is little important. The extent of S-O bond cleavage increases with increasing the basicity of the amines, but decreases with increasing the basicity of the nucleophilic aryloxides, indicating that the HSAB principle is not always operative. Besides, reactant and solvent polarizability effect has also been found to be an important factor in some cases but not always to influence the reaction site.
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자연과학대학 > 화학·나노과학전공 > Journal papers
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