β-diketone interactions: Part 5. Solvent effects on the keto ⇋ enol equilibrium
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Cyclic enaminone as new chemotype for selective cyclooxygenase-2 inhibitory, anti-inflammatory, and analgesic activities
2019, European Journal of Medicinal ChemistryCitation Excerpt :However, whether the reaction would proceed through ‘path a’ or ‘path b’ would be dependent on to what extent the starting cyclic β-diketone exists in the keto or enol form. Generally in non-polar solvent the keto form exists exclusively or predominantly [43] whereas polar solvents (particularly protic polar) direct the equilibrium towards the enol from [44]. Moreover, apart from the popularly considered dielectric constant (ε), the other less frequently considered physico-chemical parameters such as the acceptor number (AN) and donor number (DN) also play crucial role in promoting organic reactions [45,46].
Structure, stability and conversions of tautomers and rotamers of azulene-based uracil analogue
2019, Journal of Molecular StructureCitation Excerpt :The acidity of H α to the CO group is an important factor in keto-enol tautomerism. The more acidic H8, the more the equilibrium favors the enol form [88]. Therefore, we calculate the deprotonation enthalpy of N1H8 of AZU1 and O9H8 of AZU8 at B3LYP/6-31 + G (d, p), see Table 1S.
Handbook of Solvents, Volume 1: Properties, Third Edition
2019, Handbook of Solvents, Volume 1: Properties, Third EditionStudy of the novel fluorescent 4-methyl-9-(3-oxobutanoyl)-2H,8H-pyrano[2,3-f]chromene-2,8-dione derivative. Estimation of the ground- and excited-state dipole moments from a solvatochromic shift
2017, Journal of Molecular StructureCitation Excerpt :Different techniques have been used to perform extensive experimental and theoretical studies on ground-state and excited-state dipole moments for a variety of organic fluorescent compounds, such as coumarins [28–31]. In continuation of our studies on optical properties of new compounds [5,32–34], we describe herein the estimation of the ground- and excited-state dipole moments and the fluorescence quantum yields of 4-methyl-9-(3-oxobutanoyl)-2H,8H-pyrano[2,3-f]chromene-2,8-dione 3, recently synthesized in our laboratory [35] (Scheme 2), and compared with those of 3-acetoacetyl-benzo[f]coumarin 4 [5] and 3-acetoacetyl-7-methylpyranopyran-2,5-dione 5 [33] (Scheme 3). Compound 3 was synthesized as reported in the literature [35] and its structure and purity was confirmed by NMR spectroscopy and MS spectroscopy.
The acetylacetone-water complex in a low-temperature solid argon matrix
2017, Journal of Molecular Spectroscopy