Oxidation of D-glucose-1-d and methyl-alpha and Bbeta-D-glucopyranoside-1-D by aqueous chlorine
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The kinetic isotope effect on oxidation of D-glucose-1-d and methyl-alpha and beta-D-glucopyranoside-1-d by aqueous chlorine was investigated in 1 M HClO4 and at pH 1, 5 and 11. D-Glucose-1-d was synthesized by reducing D-gluconic-delta-lactone with sodium borodeuteride (1). The latter was made by the method of Schlesinger et al. (2). Methyl-D-glucopyranosides-1-d were prepared by direct methylation (3). Analysis by mass spectograph indicated 98 + atom percent deuterium. Deuterium was shown to be at C-1 by hydrolysis of methyl-D-glucopyranoside-1-d and oxidation (4) OF D-glucose-1-d to deuterium-free potassium D-gluconate. Rate measurements were carried out with a large excess of sugar (pseudo-zero order in sugar). The reaction rate at 25 degrees was followed iodometrically (5), with a hypodermic syringe as reaction vessel. The ionic strength (two in the acidic region and one in the alkaline region) was maintained constant with sodium perchlorate. The buffer solutions were: 0.296 M phosphoric acid and .300 M NaH2PO4 for pH 1; .800 M NaH2PO4 and .200 M Na2HPO4 for pH 5; and .100 M Na2HPO4 and .100 M sodium hydroxide for pH 11 [TRUNCATED]
Thesis (Ph.D.)--Boston University
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