The acid-catalyzed hydrolysis of methyl 2-chloro-2-deoxy-β-D-glucopyranoside
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The kinetics of the hydrolysis of methyl 2-chloro-2-deoxy-β-D-glucopyranoside have been determined in hydrochloric acid solutions over a range of acid concentrations and temperatures. Chloro substitution reduces the rate by a factor of 35 compared with the hydroxy analogue. Application of the Hammett criterion indicates a unimolecular (A-1) mechanism of hydrolysis, as does application of the Bunnett criterion. The entropy of activation, however, is considerably smaller than that observed for the hydrolysis of methyl β-d-glucopyranoside. This is interpreted as being indicative of partial A-2 character.
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1976 ◽
pp. 2440
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1980 ◽
Vol 58
(5)
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pp. 594-600
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2013 ◽
Vol 94
(1)
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pp. 13-16
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2010 ◽
Vol 2010
(12)
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pp. 1110-1113
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