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Regioselectivity of the interaction of temozolomide with borane and boron trifluoride

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Abstract

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.

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Acknowledgments

The authors thank Mireille Bilonda Kabuyi of the University of Venda, Republic of South Africa, for fruitful collaboration.

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Authors and Affiliations

  1. Faculty of Sciences, University of Kinshasa, B.P. 190, Kinshasa XI, Democratic Republic of the Congo

    Okuma Emile Kasende & Jules Tshishimbi Muya

  2. Department of Chemistry and Biochemistry, Utah State University, Logan, UT, 84322-0300, USA

    Steve Scheiner

Authors
  1. Okuma Emile Kasende
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  2. Jules Tshishimbi Muya
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  3. Steve Scheiner
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Corresponding author

Correspondence to Steve Scheiner.

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This paper is dedicated to Professor Magdolna Hargittai on the occasion of her 70th birthday.

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Kasende, O.E., Muya, J.T. & Scheiner, S. Regioselectivity of the interaction of temozolomide with borane and boron trifluoride. Struct Chem 26, 1359–1365 (2015). https://doi.org/10.1007/s11224-015-0640-6

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  • DOI: https://doi.org/10.1007/s11224-015-0640-6

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