QUANTUM-CHEMICAL STUDY OF THE MECHANISM OF DISPROPORTIONATION OF 2,5-DIETHYL-3,4-DIHYDRO-2<i>H</i>-PYRAN-2-CARBALDEHYDE IN THE CANNIZZARO REACTION
DOI:
https://doi.org/10.1007/1235Keywords:
2, 5-diethyl-3, 4-dihydro-2H-pyran-2-carbaldehyde, (2, 4-dihydro-2H-pyran-2 yl)methanol, sodium 2, 4-dihydro-2H-pyran-2-carboxylate, Cannizzaro reaction, quantum-chemical calculations, RM1 methodAbstract
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.]
