pH- and wavelength-dependent photodecarboxylation of ketoprofen

Org Lett. 2011 Oct 21;13(20):5472-5. doi: 10.1021/ol202182k. Epub 2011 Sep 21.

Abstract

The pH- and wavelength-dependent pathways for the photodecarboxylation of ketoprofen (KP) were mapped by CASSCF/CASPT2 computations. The decarboxylation of the basic form (KP(-)) was found to start from a long-distance charge transfer (CT) excited state when populated by photoexcitation at 330 nm. A short-distance CT excited state populated with photoexcitation at λ < 260 nm appears to be responsible for the decarboxylation of the acidic form (KP). The H(2)O molecules function as a bridge to assist proton transfer in the reactions examined here.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Hydrogen-Ion Concentration
  • Ketoprofen / chemistry*
  • Molecular Structure
  • Photochemical Processes

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Ketoprofen