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Abstract:

The UV-absorption, fluorescence excitation and emission spectra of the 6-chloro-, 8-chloro-, 6,8-dichloro-derivatives of nor-harmane, harmane and harmine and the 8-chloro-derivative of harmol were studied. These studies were performed in EtOH and in EtOH + 1% perchloric acid solutions (pa). Furthermore, fluorescence quantum yields (φf) in both media and in acetonitrile and acetonitrile + 1% perchloric acid solutions at 298 K were measured. The HOMO and LUMO energy, the positions (λmax) and oscillator strength (f) of the 1S1 ← 1S0 band for all the neutral and protonated β-carbolines studied were calculated and compared with the experimental data. The pKa values in aqueous solution for for 6-chloro-, 8-chloro- and 6,8-dichloro-nor-harmane, harmane and harmine and 8-chloro-harmol were spectrophotometrically measured (pKa(H2O)). The change of the acid-base character of these compounds on going from the ground state (pKa) to the first electronic excited singlet state (pKa*) as Δ pKa = pKa* - pKa, in ethanol solution at 298 K were calculated (ΔpKa(EtOH)). Ground-state proton affinity (PA) for all the compounds studied defined as minus the enthalpy change of the reaction M + H+ → MH+ (gas state) were calculated. Basicity relative to pyridine (ΔHrPy) defined as the enthalpy change of the isodesmic reaction MH+ + Py → M + PyH+ in gas state and in water solution, were also calculated (ab initio calculations). The effect of chlorine as substituent on the photochemistry and acid-base properties of the β-carboline alkaloids is discussed. © 2005 Elsevier B.V. All rights reserved.

Registro:

Documento: Artículo
Título:Effect of chlorine as substituent on the photochemistry and acid-base properties of β-carboline alkaloids
Autor:Tarzi, O.I.; Erra-Balsells, R.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón II, 1428-Buenos Aires, Argentina
Palabras clave:Chloro-β-Carbolines; Chloro-harmane; Chloro-harmine; Chloro-harmol; Chloro-nor-harmane; 6 chloroharmane; 6 chloroharmine; 6 chloronorharmane; 6,8 dichloroharmane; 6,8 dichloroharmine; 6,8 dichloronorharmane; 8 chloroharmane; 8 chloroharmine; 8 chloroharmol; 8 chloronorharmane; acetonitrile; alcohol; alkaloid derivative; beta carboline; beta carboline derivative; chlorine; harman; perchloric acid; unclassified drug; acid base balance; aqueous solution; article; calculation; chemical reaction; controlled study; drug structure; enthalpy; flame photometry; fluorescence analysis; oscillation; photochemistry; priority journal; proton transport; quantum yield; radiation absorption; spectrophotometry; structure analysis; ultraviolet radiation; Carbolines; Chlorine; Harmine; Hydrogen-Ion Concentration; Molecular Structure; Photochemistry; Spectrometry, Fluorescence; Spectrophotometry, Ultraviolet; Ultraviolet Rays; Water
Año:2006
Volumen:82
Número:2
Página de inicio:79
Página de fin:93
DOI: http://dx.doi.org/10.1016/j.jphotobiol.2005.09.001
Título revista:Journal of Photochemistry and Photobiology B: Biology
Título revista abreviado:J. Photochem. Photobiol. B Biol.
ISSN:10111344
CODEN:JPPBE
CAS:acetonitrile, 75-05-8; alcohol, 64-17-5; beta carboline, 244-63-3; chlorine, 13981-72-1, 7782-50-5; harman, 486-84-0; perchloric acid, 7601-90-3; Carbolines; Chlorine, 7782-50-5; Harmine, 442-51-3; Water, 7732-18-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10111344_v82_n2_p79_Tarzi

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Citas:

---------- APA ----------
Tarzi, O.I. & Erra-Balsells, R. (2006) . Effect of chlorine as substituent on the photochemistry and acid-base properties of β-carboline alkaloids. Journal of Photochemistry and Photobiology B: Biology, 82(2), 79-93.
http://dx.doi.org/10.1016/j.jphotobiol.2005.09.001
---------- CHICAGO ----------
Tarzi, O.I., Erra-Balsells, R. "Effect of chlorine as substituent on the photochemistry and acid-base properties of β-carboline alkaloids" . Journal of Photochemistry and Photobiology B: Biology 82, no. 2 (2006) : 79-93.
http://dx.doi.org/10.1016/j.jphotobiol.2005.09.001
---------- MLA ----------
Tarzi, O.I., Erra-Balsells, R. "Effect of chlorine as substituent on the photochemistry and acid-base properties of β-carboline alkaloids" . Journal of Photochemistry and Photobiology B: Biology, vol. 82, no. 2, 2006, pp. 79-93.
http://dx.doi.org/10.1016/j.jphotobiol.2005.09.001
---------- VANCOUVER ----------
Tarzi, O.I., Erra-Balsells, R. Effect of chlorine as substituent on the photochemistry and acid-base properties of β-carboline alkaloids. J. Photochem. Photobiol. B Biol. 2006;82(2):79-93.
http://dx.doi.org/10.1016/j.jphotobiol.2005.09.001