Quantum chemical evaluation of the yield of hydroxybenzophenones in the Fries rearrangement of hydroxyphenyl benzoates

The Fries rearrangement of resorcinol monobenzoate and orcinol monobenzoate was studied by using various molecular modelling approaches. The conformational analysis of the reactants and products was accomplished. The methods used were the molecular mechanical MM+ approach, the Hartree–Fock method wi...

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Bibliographic Details
Published in:Journal of molecular structure. Theochem 2004-12, Vol.712 (1), p.215-221
Main Authors: Metsala, Andrus, Usin, Eve, Vallikivi, Imre, Villo, Ly, Pehk, Tõnis, Parve, Omar
Format: Article
Language:English
Subjects:
Ab initio calculations
Conformational analysis
Fries rearrangement
Monobenzoate
Orcinol
Polyhydroxybenzophenone
Resorcinol
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Summary:The Fries rearrangement of resorcinol monobenzoate and orcinol monobenzoate was studied by using various molecular modelling approaches. The conformational analysis of the reactants and products was accomplished. The methods used were the molecular mechanical MM+ approach, the Hartree–Fock method with an STO-3G basis set and the density functional method B3LYP with basis sets 3-21G, 6-31G and 6-31+G*. The results obtained by using the B3LYP/6-31+G* method, unlike those obtained by using the lower-level methods, allowed calculation of the values of the thermodynamic distribution of isomeric components in equilibrium mixtures (monobenzoate/benzophenone) that appeared to be in good accordance with the experimental results.
ISSN:0166-1280
1872-7999
DOI:10.1016/j.theochem.2004.10.025