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Title: Predicting the hydroxymethylation rate of phenols with formaldehyde by molecular orbital calculation.
Author: Mitsunaga, Tohru; Conner, Anthony H.; Hill, Charles G. Jr.;
Source: Journal of wood science. Vol. 48 (2002). Pages 153-158.
Publication Series: Miscellaneous Publication
Description: The rates (k) of hydroxymethylation of phenol, resorcinol. phloroglucinol, and several methylphenols in diluted 10% dimethylformamide aqueous alkaline solution were calculated based on the consumption of phenols and formaldehyde. The k values of phloroglucinol and resorcinol relative to that of phenol were about 62000 and 1200 times, respectively. The phenols that have methyl or hydroxyl groups at the C-3 or C-5 position (or both) have larger rate constants than phenols with substituents at other positions. Several kinds of atomic charge of the carbons on the aromatic ring of phenols were calculated using the semiempirical or ab initio method. The correlations between the average k (Ave.k) and average electrostatic charges (Ave.q) at the carbons were fairly good. Highest occupied molecular orbitals (HOMO) were observed. The best correlation between Ave.k and Ave.q was obtained when diphenols and triphenols were assumed to exist in solution as their respective di-anion.
Keywords: Chemical computation, Ab initio, Semiempirical, Phenolic compounds, Formaldehyde.
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Mitsunaga, Tohru; Conner, Anthony H.; Hill, Charles G., Jr. 2002. Predicting the hydroxymethylation rate of phenols with formaldehyde by molecular orbital calculation. Journal of wood science. Vol. 48 (2002). Pages 153-158.
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