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Title: 1,3-Cycloaddition of Ozone to Ethylene, Benzene, and Phenol: A Comparative ab Initio Study
Journal: J. Phys. Chem. A
Volume: 107
Page(s): 7574 - 7580
Year: 2003
Reference type: Journal article
Squib: 2003HEN/VIN7574-7580
Reaction:
Phenol + O3 → 1,2-Dihydroxybenzene + O2
Reaction order:
2
Rate expression:
no rate data available
Category: Theory
Data type:
Ab initio
Comments:
No rate constants reported. Barriers and heats of reactions only. Quantum calculations of addition of ozone to ethylene, benzene and phenol. For phenol, there are three possible addition channels: 1,2-, 2,3-, and 3,4-. For the 1,2-addition channel (the favored channel), it is believed that the molecule eventually decomposes to catechol (1,2-Dihydroxybenzene). Fair to good agreement between ab initio calculations and experimental values for Ethylene and Benzene reactions are obtained. No experimental data exists for the Phenol reactions.
Geometries at B3LYP/6-31G(d,p). Energies at CCSD(T)(/6-31G(d,p). Energies reported here include ZPE but not thermal correction to 298 K.
Ethylene + O3 -> 1,2,3-Trioxolane Ea = 3.3 kcal/mol Hr = -52.5 kcal/mol
Benzene + O3 -> Benzotrioxole Ea = 15.8 kcal/mol Hr = -18.6 kcal/mol
Phenol + O3 -> Benzotrioxolol Ea = 9.5 kcal/mol Hr = -27.1 kcal/mol/
Phenol + O3 -> 4-Benzotrioxolol Ea = 12.5 kcal/mol Hr = -23.3 kcal/mol/
Phenol + O3 -> 5-Benzotrioxolol Ea = 11.3 kcal/mol Hr = -23.3 kcal/mol/
Benzotrioxole (Benzene primary ozonide)
Benzotrioxolol (Phenol primary 1,2-ozonide)
4-Benzotrioxolol (Phenol primary 2,3-ozonide)
5-Benzotrioxolol (Phenol primary 3,4-ozonide)
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