The aldol condensation of acetone with acetophenone

Guthrie, J. Peter; Wang, Xiaoping

doi:10.1139/v92-140

Cited by 18 publications

(13 citation statements)

References 17 publications

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“…This step was predicted to be 9 x lo3 times faster than the analogous rate constant for acetone plus acetophenone, for which we have measured the overall rate constant (38).…”

Section: Conjecture 1 : Marcus Theory Is Generally Applicable To Orgamentioning

confidence: 73%

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1995 Syntex Award Lecture Correlation and prediction of rate constants for organic reactions

Guthrie¹

1996

Can. J. Chem.

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Abstract:Marcus theory provides a framework for correlating rate and equilibrium constants, and thus the possibility of predicting rate from structure. This had been successful for a number of simple reactions, including the addition of hydroxide to carbonyl compounds, enolate formation from carbonyl compounds, and aldol addition and elimination reactions. The theory can be extended, as Multidimensional Marcus Theory, to cover concerted reactions such as E2 eliminations, the water-mediated proton switch, or the breakdown of the tetrahedral intermediate in amide hydrolysis. We have now found that Marcus theory can be applied not only to inter-molecular reactions but also to intra-molecular reactions. This is illustrated for aldol condensation and esterllactone formation.Key words: Marcus theory, concerted reactions, intramolecular reactions, aldol condensation, ester formation, proton transfer.Resume : La thCorie de Marcus offre un s y s t h e pour Ctablir des corrClations entre les constantes de vitesse et dlCquilibre et, de ce fait, la possibilitC de faire des pridictions relatives aux vitesses ii partir des structures. Cette approche a Ct C couronnke de succks pour un certain nombre de rCactions simples, y compris l'addition de l'ion hydroxyde ii des composks carbonylks, la formation d'Cnolates 5 partir de composCs carbonylks et les rkactions d'addition et d'klimination aldoliques. On a ktendue la thiorie, sous la forme de la thCorie multidimensionnelle de Marcus, pour couvrir les rCactions concertkes, comme les Climinations E2, 1'Cchange de protons avec l'eau comme mCdiateur ou 1adCpyramidalisation de l'intermkdiaire tCtraCdrique lors de l'hydrolyse des amides. On a trouvC que la thCorie de Marcus peut &tre appliquCe, non seulement aux rCactions inter~nolCculaires mais aussi aux rCactions intramolCculaires. On illustre ce point par la condensation aldolique et le formation d'esterllactone.

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“…This step was predicted to be 9 x lo3 times faster than the analogous rate constant for acetone plus acetophenone, for which we have measured the overall rate constant (38).…”

Section: Conjecture 1 : Marcus Theory Is Generally Applicable To Orgamentioning

confidence: 73%

“…The detailed kinetics have been worked out, and the rate constant for the reaction of acetone enolate with a,a,a-trifluoroacetophenone can be calculated; as predicted it is much faster than the corresponding rate constant for acetone plus acetophenone (38). The actual rate ratio is 7.5 x lo3.…”

Section: Conjecture 1 : Marcus Theory Is Generally Applicable To Orgamentioning

confidence: 88%

1995 Syntex Award Lecture Correlation and prediction of rate constants for organic reactions

Guthrie¹

1996

Can. J. Chem.

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“…By adopting the literature precedent (21), (E)-1-naphthalen-2-yl)-3-arylprop-2-en-1-ones 1-8 were prepared.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and anticandidiasis activity of novel (2E)-ethyl-2-(2-(2,4-dinitrophenyl)hydrazono)-4(naphthalen-2-yl)-6-arylcyclohex-3-ene carboxylates

Kanagarajan

Gopalakrishnan

2010

Pharm Chem J

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In a search for new leads towards potent antifungal agents against candidiasis, a series of novel (2E)-ethyl-2-(2-(2,4-dinitrophenyl)hydrazono)-4-(naphthalen-2-yl)-6-arylcyclohex-3-ene carboxylates 17 -24 is synthesized and characterized by their physical and analytical data. In vitro microbiological evaluations for all the newly synthesized compounds against clinically isolated Candida sp. are carried out, and their structure-activity effect is discussed.

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“…Adopting the literature reports 1,3-diaryl-prop-2-en-1-ones 1-11 [28] and 2-amino-4,6-diarylpyrimidines 12-22 [29], were synthesized.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, spectral analysis andin vitromicrobiological evaluation of 2-phenyl-3-(4,6-diarylpyrimidin-2-yl)thiazolidin-4-ones

Gopalakrishnan

Thanusu

Kanagarajan

2009

Journal of Enzyme Inhibition and Medicinal Chemistry

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The aldol condensation of acetone with acetophenone

Cited by 18 publications

References 17 publications

1995 Syntex Award Lecture Correlation and prediction of rate constants for organic reactions

1995 Syntex Award Lecture Correlation and prediction of rate constants for organic reactions

Synthesis and anticandidiasis activity of novel (2E)-ethyl-2-(2-(2,4-dinitrophenyl)hydrazono)-4(naphthalen-2-yl)-6-arylcyclohex-3-ene carboxylates

Design, synthesis, spectral analysis andin vitromicrobiological evaluation of 2-phenyl-3-(4,6-diarylpyrimidin-2-yl)thiazolidin-4-ones

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