DENSITY FUNCTIONAL STUDY OF BOND DISSOCIATION ENERGIES IN HIGHLY BROMINATED DIPHENYL ETHERS
Keywords:
brominated flame retardants, decabromodiphenyl ether, density functional theory, bond dissociation energiesAbstract
Bond dissociation enthalpies (DEs) relevant to thermal dissociation of brominated diphenyl ethers were investigated in a computational approach at the density functional theory (DFT) level. In a preliminary assessment of eight of the most popular exchange-correlation functionals (including B3P86, PBE1PBE, mPW1PW91, wB97xD and two of each of the M05 and M06 families) the M06 meta-hybrid is shown to perform the best in reproducing two experimental C-O and C-Br BDEs, with errors bellow 1 kcal/mol and less dependent on basis set. The M06/cc-pVDZ is chosen as a good compromise between cost and accuracy for computing DEs of seven brominated diphenyl ethers. In the case of decabromodiphenyl ether we report a DE of 68.7 kcal/mol for the homolysis of the ether group and 74 to 77 kcal/mol for bromine cleavage. Compared to the corresponding values of the fully brominated compound, in lower brominated congeners we predict a substantial increase of both DEs with the decrease of bromine content.
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