Solvent effects on the sensitized photoxygenation of lidocaine

Antonio L. Zanocco, Else Lemp, Nancy Pizarro, Julio R. De La Fuente, German Günther

Resultado de la investigación: Contribución a una revistaArtículo

16 Citas (Scopus)


Detection of O2(1Δg) phosphorescence emission, λmax=1270nm, following laser excitation and steady state methods were employed to determine both the total constant, kT LID, and the chemical reaction rate constants, kR LID, for reaction between the anaesthetic lidocaine and singlet oxygen in several solvents. Values of kT LID range from 0.20±0.09×106M-1s-1 in trifluoroethanol to 45.8±2.40×106M-1s-1 in N,N-dimethylacetamide. Values of kR LID are at least one order of magnitude lower than kT LID values in a given solvent. Solvent effect on quenching rates shows that reaction mechanism involves formation of a charge transfer exciplex. Correlation of kT LID values with solvent parameters does not follow that observed for a typical tertiary amine such as triethylamine. Although kT LID values are lower in hydrogen bond donor solvents, this solvent effect is significantly smaller than that for triethylamine, and no expected decrease in lidocaine reactivity with change from aprotic to protic solvents was found. This result is ascribed to weaker hydrogen bonding between the amino moiety in lidocaine and the solvent. Otherwise, hydrogen bond acceptor solvents increase kT LID to a greater extent than that triethylamine. This can be explained by intra-molecular hydrogen bonding or electrostatic interactions that stabilize lidocaine and hydrogen bond acceptor solvents disrupt these interactions.

Idioma originalInglés
Páginas (desde-hasta)109-115
Número de páginas7
PublicaciónJournal of Photochemistry and Photobiology A: Chemistry
EstadoPublicada - 10 may 2001

Áreas temáticas de ASJC Scopus

  • Química (todo)
  • Ingeniería química (todo)
  • Física y astronomía (todo)

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