Publications [#232097] of Patrick Charbonneau

Papers Published

1. Charbonneau, P; Jean-Claude, B; Whitehead, MA, Synthesis of a prodrug: A semi-empirical PM3 study, Journal of Molecular Structure THEOCHEM, vol. 574 no. 1-3 (November, 2001), pp. 85-91, Elsevier BV, ISSN 0166-1280 [doi]
   (last updated on 2026/01/18)

   Abstract:
   The semi-empirical PM3 method is used to investigate the synthesis of a prodrug of type I which can regenerate the short-lived anti-tumoral tetrazepinone. The reaction pathway examined involves four consecutive steps: the ring opening of benzo-tetrazepinone (1 → 2), the diazonium coupling (2 → 3), the double-proton transfer (4 → 6) and the dissociation (7 → 8). Geometry PM3 optimisation of all starting material, reaction intermediates and products lead to a qualitative study of this solvent-dependent synthesis. Energetics and substituent effects are analysed using a simple electron-withdrawing, electron-donating argument based on calculated Hammett constants. © 2001 Published by Elsevier Science B.V.