From lithium ketazides to isomeric silylketazine-rings – imine-enamine tautomerism

Armbruster, Nina; Görth, Martin; Klingebiel, Uwe; Schmatz, Stefan

doi:10.1016/j.jorganchem.2007.10.033

Cited by 3 publications

(2 citation statements)

References 17 publications

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“…As it will be seen later in the text, these compounds come predominantly in two tautomeric forms: the imine (a) and the enamine (c) ones of Scheme 1. The imine-enamine tautomerism has been the subject of continuous interest in chemistry and the effects of substituting functional groups on this equilibrium [21] have been the focus of several computational investigations.…”

Section: Introductionmentioning

confidence: 99%

How to drive imine–enamine tautomerism of pyronic derivatives of biological interest – A theoretical and experimental study of substituent and solvent effects

Amar¹,

Meghezzi²,

Boucekkine³

et al. 2010

Comptes Rendus. Chimie

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An investigation of the tautomerism of five series of aminated pyronic compounds of pharmacological interest was carried out using NMR experiments and standard quantum mechanical B3LYP/6-311+G** calculations. The obtained results indicate that among four possible tautomers, imine and enamine forms are the two predominating ones in the gas phase as well as in solution. Depending on the nature of the substituting group, the enamine or the imine form is the most stable tautomer, the calculations being in agreement with experiment. The calculated equilibrium constants in the gas phase and in solution show that the enamine form is stabilized by polar solvents, in all cases. NBO analysis explains well the predominance of a form over another one when changing a substituting group. We give indications on how to favour the imine form which is preferred for synthesis purposes.

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Section: Introductionmentioning

confidence: 99%

How to drive imine–enamine tautomerism of pyronic derivatives of biological interest – A theoretical and experimental study of substituent and solvent effects

Amar¹,

Meghezzi²,

Boucekkine³

et al. 2010

Comptes Rendus. Chimie

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“…Die Chemie der Cyclosilazane ist gut untersucht [85] . Im Folgenden soll die Reaktion [26] mit lithiierten Hydrazonen und Azinen, 42 -48 [86] Lithiierte Hydrazone und Azine [87] reagieren mit dem 2,2-Difluor-1,3-diaza-2silacyclopenten I [26] zu cyclischen-bzw. durch Imin-Enamin-Tautomerie acyclischensubstituierten Verbindungen.…”

Section: Umsetzung Des Dilithiumsalzes Nn`-di-tert-butyl-14-diaza-13-...unclassified

Fluorfunktionelle 1,3-Diaza-2-sila-cyclopentene -Synthese, Reaktionen und Kristallstrukturen

Fischer¹

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Substituent effects on the tautomerism of monochalcogenocarboxylic acids XC(O)YH (X=H, F, NH2, OH, CN, and CH3; Y=S, Se, and Te): A theoretical study

Huang

Xia

2009

Journal of Molecular Structure: THEOCHEM

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From lithium ketazides to isomeric silylketazine-rings – imine-enamine tautomerism

Cited by 3 publications

References 17 publications

How to drive imine–enamine tautomerism of pyronic derivatives of biological interest – A theoretical and experimental study of substituent and solvent effects

How to drive imine–enamine tautomerism of pyronic derivatives of biological interest – A theoretical and experimental study of substituent and solvent effects

Fluorfunktionelle 1,3-Diaza-2-sila-cyclopentene -Synthese, Reaktionen und Kristallstrukturen

Substituent effects on the tautomerism of monochalcogenocarboxylic acids XC(O)YH (X=H, F, NH2, OH, CN, and CH3; Y=S, Se, and Te): A theoretical study

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