Richard W Nagorski

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The deuterium enrichment of dihydroxyacetone obtained from the aldose-ketose isomerization of D,L-glyceraldehyde in D(2)O at 25 degrees C was determined by (1)H NMR spectroscopy from the integrated areas of the signals for the alpha-CH(2) and alpha-CHD groups of the product. One mole equivalent of deuterium is incorporated into the product when the(More)
[figure: see text] The rate constants for the hydronium ion, hydroxide, and water-catalyzed breakdown of N-(hydroxymethyl)benzamide (1), 4-chloro-N-(hydroxymethyl)benzamide (2), and 2,4-dichloro-N-(hydroxymethyl)benzamide (3) in H2O, at 25 degrees C, I = 1.0 (KCl), have been determined. The reactions of 1, 2, and 3 were found to be specific acid and(More)
The induction of strain in carbocycles, thereby increasing the amount of s-character in the C-H bonds and the acidity of these protons, has been probed with regard to its effect on the rate constants for the enolization of cyclobutanone. The second-order rate constants for the general base-catalyzed enolization of cyclobutanone have been determined for a(More)
The kinetic study of the aqueous reaction, between pH 10 and 14, of eight N-(hydroxymethyl)benzamide derivatives in water at 25 degrees C, I = 1.0 M (KCl), has been performed. In all cases, the reaction proceeds via a specific-base-catalyzed deprotonation of the hydroxyl group followed by rate-limiting breakdown of the alkoxide to form aldehyde and amidate(More)
[reaction: see text] The 3-quinuclidinone-catalyzed (pK(BH) = 7.5) enolization of cyclobutanone (1) in D(2)O at 25 degrees C, I = 1.0 (KCl) was followed by deuterium incorporation, which was determined by (1)H NMR. The second-order rate constant for the buffer-catalyzed deprotonation of 1 was found to be k(B) = 3.3 x 10(-4) M(-1) s(-1), which is compared to(More)
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