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: Article

16 Citas (Scopus)

Resumen

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 originalEnglish
Páginas (desde-hasta)109-115
Número de páginas7
PublicaciónJournal of Photochemistry and Photobiology A: Chemistry
Volumen140
N.º2
DOI
EstadoPublished - 10 may 2001

Huella dactilar

Lidocaine
Hydrogen bonds
hydrogen bonds
Trifluoroethanol
anesthetics
Anesthetics
Phosphorescence
Singlet Oxygen
Laser excitation
hydrogen
phosphorescence
Coulomb interactions
Reaction rates
Amines
Charge transfer
Chemical reactions
Quenching
Rate constants
chemical reactions
amines

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Physics and Astronomy(all)

Citar esto

Zanocco, Antonio L. ; Lemp, Else ; Pizarro, Nancy ; De La Fuente, Julio R. ; Günther, German. / Solvent effects on the sensitized photoxygenation of lidocaine. En: Journal of Photochemistry and Photobiology A: Chemistry. 2001 ; Vol. 140, N.º 2. pp. 109-115.
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abstract = "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.",
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Solvent effects on the sensitized photoxygenation of lidocaine. / Zanocco, Antonio L.; Lemp, Else; Pizarro, Nancy; De La Fuente, Julio R.; Günther, German.

En: Journal of Photochemistry and Photobiology A: Chemistry, Vol. 140, N.º 2, 10.05.2001, p. 109-115.

Resultado de la investigación: Article

TY - JOUR

T1 - Solvent effects on the sensitized photoxygenation of lidocaine

AU - Zanocco, Antonio L.

AU - Lemp, Else

AU - Pizarro, Nancy

AU - De La Fuente, Julio R.

AU - Günther, German

PY - 2001/5/10

Y1 - 2001/5/10

N2 - 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.

AB - 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.

KW - Lidocaine

KW - LSER

KW - Photosensitization

KW - Singlet oxygen

KW - Solvent effect

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JO - Journal of Photochemistry and Photobiology A: Chemistry

JF - Journal of Photochemistry and Photobiology A: Chemistry

SN - 1010-6030

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