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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 7
BKCSDE 31(7)
July 20, 2010

Title	Correlation of the Rates of Solvolysis of 4-Morpholinecarbonyl Chloride Using the Extended Grunwald-Winstein Equation
Author	Ran Kim, Dildar Ali, Jong Pal Lee, Kiyull Yang, In Sun Koo
Keywords	4-Morpholinecarbonyl chloride (MPC), Grunwald-Winstein equation, Addition-elimination (A-E), Ionization (I), KSIE
Abstract	The rates of solvolysis of 4-morpholinecarbonyl chloride (MPC) have measured at 35.0 ^oC in water, D₂O, CH₃OD, and in aqueous binary mixtures of acetone, ethanol, methanol, and 2,2,2-trifluoroethanol. An extended (two-term) Grunwald-Winstein equation correlation gave sensitivities towards changes in solvent nucleophilicity and solvent ionizing power as expected for a dissociative S_N2 and/or S_N1(ionization) pathway. For nine solvents specific rates were determined at two additional temperatures and higher enthalpies and smaller negative entropies of activation were observed, consistent with the typical dissociative SN2 or S_N1(ionization) pathway. The solvent deuterium isotope effect values for the hydrolysis of MPC of k_H2O/k_D2O = 1.27 and for the methanolysis of MPC of k_MeOH/k_MeOD = 1.22 are typical magnitudes of the S_N1 or ionization mechanism.
Page	1963 - 1967
Full Text	PDF

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