Quality Control of 2,6-Dimethyl-3,5-heptanedione. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2,6-Dimethyl-3,5-heptanedione, is researched, Molecular C9H16O2, CAS is 18362-64-6, about Kinetics of proton transfer of 3,5-heptanedione, 2,6-dimethyl-3,5-heptanedione, and dibenzoylmethane with amines in 50% dimethyl sulfoxide-50% water. Effect of steric crowding and π-overlap on intrinsic rate constants. Author is Bernasconi, Claude F.; Ohlberg, Douglas A. A.; Stronach, Michael W..
Rates of reversible deprotonation of 3,5-heptanedione (I), 2,6-dimethyl-3,5-heptanedione (II), and dibenzoylmethane (III) by several primary aliphatic amines, by piperidine and morpholine, and by hydroxide ion (I and III only) have been measured in 50% Me2SO-50% water (volume/volume) at 20°. Apparent pKa’s as well as the pKa values of the keto and the enol forms, and the enolization equilibrium constants (KT) were also determined The pKa and KT values show the same trends observed previously in water. The intrinsic rate constants for the reactions of I and II with a given family of amines (primary aliphatic or secondary alicyclic) are the same and also equal to those for the reaction of acetylacetone (IV) with the same amines determined previously. These results indicate that steric effects play an insignificant role in the reactions of I, II, and IV. The intrinsic rate constants for the deprotonation of III are approx. three fold lower than for I, II, and IV. This reduction is shown not be caused by a steric effect but by π-overlap with the Ph groups in the enolate ion.
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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica