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MP2 and B3LYP calculations are used to predict the most favorable site of temozolomide toward BH3 and BF3 which are classical Lewis acids. Binding energies, charge transfers, and bond length perturbations of the temozolomide in various complexes indicate that the N12 atom is the preferred attack site for BH3, while BF3 prefers the O17 atom. The interactions are quite strong, as much as 100 kJ/mol for BH3 and more than 60 kJ/mol for BF3. The molecular electrostatic potential surrounding temozolomide is most negative around the O atoms, which is unable to explain the energetic order of binding of the Lewis acids.
Kasende, O., Muya, J. T., Scheiner, S. I. (2015). Regioselectivity of the Interaction of Temozolomide with Borane and Boron Trifloride. Struct. Chem., 26, 1359-1365.
This is a post-peer-review, pre-copyedit version of an article published in Kasende, O., Muya, J. T., Scheiner, S. I. (2015). Regioselectivity of the Interaction of Temozolomide with Borane and Boron Trifloride. Struct. Chem., 26, 1359-1365. The final authenticated version is available online at: http://dx.doi.org/10.1007/s11224-015-0640-6.