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Kinetic Study on Solvolysis of 2‐Methylfuran‐3‐carbonyl Chloride in Binary Solvent Mixtures
Author(s) -
Choi Hojune,
Yang Kiyull,
Koh Han Joong,
Koo In Sun
Publication year - 2017
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11084
Subject(s) - chemistry , solvolysis , kinetic isotope effect , methanol , sn2 reaction , acetone , reaction rate constant , solvent , deuterium , reactivity (psychology) , aqueous solution , chloride , inorganic chemistry , organic chemistry , hydrolysis , kinetics , medicine , physics , alternative medicine , quantum mechanics , pathology
Rate constants for solvolysis of 2‐methylfuran‐3‐carbonyl chloride ( 1 ) in ethanol, methanol, and aqueous binary mixtures incorporating ethanol, methanol, acetone, 2,2,2‐trifluoroethanol, and 1,1,1,3,3,3‐hexafluoro‐2‐propanol are reported. The 34 solvents give an extended Grunwald–Winstein correlation with l = 0.26 ± 0.05, m = 0.71 ± 0.04, and correlation coefficient R 2 = 0.963. Activation parameters calculated from the rate constants measured at three different temperatures in five different solvents are presented. In the deuterated methanol, a solvent kinetic isotope effect of 1.15 was observed at 0°C. The kinetic features observed indicate that the reaction proceeds through an S N 1 mechanism with a little S N 2 character. The reactivity–selectivity principle is also followed in alcohol‐water mixtures.