ACID-BASE AND SPECTRAL PROPERTIES OF BETA-CARBOLINES .2. DEHYDRO AND FULLY AROMATIC BETA-CARBOLINES

被引：68
作者：
BALON, M
HIDALGO, J
GUARDADO, P
MUNOZ, MA
CARMONA, C
机构：
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1993年 / 01期
关键词：
D O I：
10.1039/p29930000099
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The absorption and fluorescence spectra of a set of dehydro and fully aromatic beta-carboline (9H-pyrido[3,4-b]indole) derivatives have been investigated in aqueous solutions of varying acidity. Within the pH-range, cationic (nitrogen protonation) and neutral species are evidenced from both absorption and fluorescence spectra. Additional zwitterionic species can also be detected from the fluorescence spectra. In highly basic media, outside the pH-range, anionic species (pyrrolic nitrogen deprotonation) are formed. Ground state ionization constants for the different acid-base equilibria involving these species have been determined spectrophotometrically at 25-degrees-C. Lowest excited singlet state pK(a)s have been estimated from the Forster-Weller cycle. The influence of structural variations on the spectra and on the acid-base properties of these compounds is discussed.
引用
收藏
页码：99 / 104
页数：6
相关论文
共 43 条
[1]   THE CARBOLINES [J].
ABRAMOVITCH, RA ;
SPENSER, ID .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1964, 3 :79-207
[2]  
ALBERT A, 1963, PHYSICAL METHODS HET, V1
[3]   THE SIMPLE BETA-CARBOLINE ALKALOIDS [J].
ALLEN, JRF ;
HOLMSTEDT, BR .
PHYTOCHEMISTRY, 1980, 19 (08) :1573-1582
[4]  
ARMAREGO WLF, 1971, PHYSICAL METHODS HET, V3, pCH4
[5]  
AULLO JM, 1979, AN QUIM-INT, V75, P11
[6]   ACID-BASE AND SPECTRAL PROPERTIES OF BETA-CARBOLINES .1. TETRAHYDRO-BETA-CARBOLINES [J].
BALON, M ;
HIDALGO, J ;
GUARDADO, P ;
MUNOZ, MA ;
CARMONA, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (01) :91-97
[7]   FLUORESCENCE CHARACTERISTICS OF BETA-CARBOLINE ALKALOIDS IN HIGHLY CONCENTRATED HYDROXIDE SOLUTIONS [J].
BALON, M ;
MUNOZ, MA ;
HIDALGO, J ;
CARMONA, MC ;
SANCHEZ, M .
JOURNAL OF PHOTOCHEMISTRY, 1987, 36 (02) :193-204
[8]   THE ACID-BASE PROPERTIES OF PYRROLE AND ITS BENZOLOGS INDOLE AND CARBAZOLE - A REEXAMINATION FROM THE EXCESS ACIDITY METHOD [J].
BALON, M ;
CARMONA, MC ;
MUNOZ, MA ;
HIDALGO, J .
TETRAHEDRON, 1989, 45 (23) :7501-7504
[9]  
BALONM, 1985, J CHEM SOC P2, P1683
[10]   FLUORESCENCE AND PHOSPHORESCENCE OF AROMATIC BETA-CARBOLINES ON DISPERSED SOLID-PHASE AT 77-K AND ROOM TEMPERATURES [J].
BERTO, JR ;
SANCHEZ, IZ ;
REVERTE, JMA ;
VERT, FT ;
TORRENT, AO .
JOURNAL OF PHOTOCHEMISTRY, 1985, 29 (3-4) :405-413
12345