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QUANTUM-CHEMICAL STUDY OF THE MECHANISM OF DISPROPORTIONATION OF 2,5-DIETHYL-3,4-DIHYDRO-2H-PYRAN-2-CARBALDEHYDE IN THE CANNIZZARO REACTION

Я. П. Ковальский, О. И. Маршалок, Н. М. Витрикуш, Г. А. Маршалок
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Abstract


The mechanism of the disproportionation of 2,5-diethyl-3,4-dihydro-2H-pyran-2-carbaldehyde in the Cannizzaro reaction in ethanol was studied by quantum-chemical modeling. The geometry was optimized by the semiempirical RM1 method in the unrestricted Hartree–Fock approximation, and the heats of formation of the reagents and transitional states were calculated. Two possible hydride transfer reaction paths are presented: through the formation of a transition state with one-center interaction or through a transition state with two-center interaction. The theoretically calculated values of the thermodynamic parameters agree with the experimental values and confirm the hydride transfer mechanism.

How to Cite
Kovalskyi, Ya. P.; Marshalok, O. I.; Vytrykush, N. M.; Marshalok, G. A. Chem. Heterocycl. Compd. 2014, 50, 7. [Khim. Geterotsikl. Soedin. 2014, 11.]

For this article in the English edition see DOI 10.1007/s10593-014-1440-4

Keywords


2,5-diethyl-3,4-dihydro-2H-pyran-2-carbaldehyde; (2,5-diethyl-3,4-dihydro-2H-pyran-2 yl)methanol; sodium 2,5-diethyl-3,4-dihydro-2H-pyran-2-carboxylate; Cannizzaro reaction; quantum-chemical calculations; RM1 method

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