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 original | English |
|---|---|
| Páginas (desde-hasta) | 109-115 |
| Número de páginas | 7 |
| Publicación | Journal of Photochemistry and Photobiology A: Chemistry |
| Volumen | 140 |
| N.º | 2 |
| DOI | |
| Estado | Published - 10 may 2001 |
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ASJC Scopus subject areas
- Chemistry(all)
- Chemical Engineering(all)
- Physics and Astronomy(all)
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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
KW - TLSER
UR - http://www.scopus.com/inward/record.url?scp=0038708354&partnerID=8YFLogxK
U2 - 10.1016/S1010-6030(01)00393-8
DO - 10.1016/S1010-6030(01)00393-8
M3 - Article
AN - SCOPUS:0038708354
VL - 140
SP - 109
EP - 115
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
SN - 1010-6030
IS - 2
ER -