6637-10-1Relevant articles and documents
Thermodynamics and kinetics of indole oligomerization in 0.5molL -1 aqueous sulfuric acid: Evaluation of some temperature-dependant parameters
Quartarone, Giuseppe,Pietropolli Charmet, Andrea,Ronchin, Lucio,Tortato, Claudio,Vavasori, Andrea
supporting information, p. 680 - 689 (2014/08/18)
Indole is present in a wide variety of natural compounds with physiological activities, as well as it is a very important intermediate in medicinal and industrial chemistry. For this reason, the evaluation of indole protonation, oligomerization equilibria and the study of the kinetics of dimer and trimer formation in diluted sulfuric acid at various temperatures are of paramount importance because of their practical and scientific implications. Here, we calculate the protonation equilibria by using the literature titration data together with a quantum chemical computational approach, in order to obtain reliable pKa value of indole from 288 to 313K. Starting from these calculations, we are able to measure the oligomerization equilibrium constants of indole, their kinetic constants, whose values are dependent of indole pK a, at different temperatures. Enthalpy and entropy of the reactions are calculated by means of Van't Hoff equation, while the activation parameters of Eyring-Evans-Polanyi equation are evaluated for the whole kinetic constants. Copyright
Nucleophilic substitution reaction at the 1-position of 1-hydroxytryptamine and -tryptophan derivatives
Yamada, Fumio,Goto, Aya,Peng, Wu,Hayashi, Toshikatsu,Saga, Yoshitomo,Somei, Masanori
, p. 163 - 172 (2007/10/03)
A novel nucleophilic substitution reaction at the 1-position of indole nucleus was discovered by reacting 1-hydroxytryptamine and -tryptophan derivatives with indoles in 85% formic acid yielding 1-(indol-3-yl)indoles. Their structures were determined by X-Ray crystallographic analysis and chemical correlations. An SN2 mechanism on the indole nitrogen (1-position) is proposed.
Nucleophilic substitution reaction on the nitrogen of indole nucleus: Formation of 1-(indol-3-yl)indoles upon reaction of 1-hydroxyindoles with indole in formic acid
Somei, Masanori,Yamada, Fumio,Hayashi, Toshikatsu,Goto, Aya,Saga, Yoshitomo
, p. 457 - 460 (2007/10/03)
1-(Indol-3-yl)indoles are obtained in excellent to good yields by the reaction of 1-hydroxyindoles with indole in 85% formic acid. Their structures are determined by X-Ray crystallographic analysis and chemical correlations. The unprecidented SN2 mechanis