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Journal articles on the topic 'Tautomerism. Ketones. Enols'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Bunting, John W., James P. Kanter, Raymond Nelander та Zhennan Wu. "The acidity and tautomerism of β-diketones in aqueous solution". Canadian Journal of Chemistry 73, № 8 (1995): 1305–11. http://dx.doi.org/10.1139/v95-161.

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The acidity and keto–enol tautomerism of a series of symmetrical β-diketones (RCOCH2COR (1): R = methyl (a), phenyl (b), 3-pyridinyl (c), 4-pyridinyl (d), 3-(N-methyl)pyridinio (e), and 4-(N-methyl)pyridinio (f)) and two series of unsymmetrical β-diketones (RCOCH2COCH3 (7a–7f) and RCOCH2COC6H5 (8a–8f)) have been investigated in aqueous solution at 25 °C and ionic strength 0.1. Values of [Formula: see text] were measured spectrophotometrically, and the acidities of the enols [Formula: see text] were obtained from the analysis of the pH dependence of the buffer catalysis for the general acid-cat

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2

Abdeldjebar, Hasnia, Yamina Belmiloud, Wassila Djitli, Sofien Achour, Meziane Brahimi, and Bahoueddine Tangour. "Proton transfer in the benzimidazolone and benzimidazolthione tautomerism process catalyzed by polar protic solvents." Progress in Reaction Kinetics and Mechanism 44, no. 2 (2019): 143–56. http://dx.doi.org/10.1177/1468678319825740.

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The tautomeric equilibrium of benzimidazolone and benzimidazolthione have been studied by the density functional theory method using the CAM-B3LYP functional together with the 6-311G(d,p) basis set. Two separate mechanisms have been investigated: a direct intramolecular transfer using the polarizable continuum model and an indirect proton transfer assisted by a molecule of solvent (C6H12, H2O, CH3OH, and H2O2). In both cases, the results obtained indicate that ketone and thione are the most stable forms. However, the enhanced height of the activation barrier for the four-center mechanisms desc

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3

Galarda, Małgorzata, and Robert Bachliński. "Identification of 2-acetyl-2-phenylacetamide (APAA) – the precursor for production of benzylmethylketone (BMK, P2P)." Issues of Forensic Science 304 (2019): 83–95. http://dx.doi.org/10.34836/pk.2019.304.3.

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The article presents the possibilities of using gas and liquid chromatography with MS detection (GC-MS, HPLC-Q-TOF) to identify 2-acetyl-2-phenylacetamide (APAA) – a precursor for the production of benzyl methyl ketone (BMK, P2P). In recent years, APAA has become very popular on the illegal drug market and its identification by the above-mentioned methods raises interpretation doubts. They are caused by BMK being present in small amounts and the ambiguous chromatographic image (GC and HPLC), which consists of two peaks with different retention times, but with the same mass spectrum. This is a

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4

Garifzianova, Guzel G. "Theoretical study of the isomerization of 1-amino-4-phenylamino-9,10-anthraquinone." Butlerov Communications 60, no. 12 (2019): 37–42. http://dx.doi.org/10.37952/roi-jbc-01/19-60-12-37.

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This paper presents the results of computer simulation of tautomeric transformations of the molecule 1-amino-4-phenylamino-9,10-anthraquinone. It is known from the literature that the presence of substituents in the 1,4-position of anthraquinone-9,10 leads to various tautomeric transformations, with a shift in the absorption maximum and the appearance of absorption bands in the red wave region in electronic spectra. Both the 1-amino-4-hydroxyanthraquinone described in the literature and the 1-amino-4-phenylamino-9,10-anthraquinone are characterized by two types of prototropic tautomerism – ket

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5

Anderson, John C., and A. Douglas Broadbent. "The influence of pH in the tautomerism of 9,10-anthracenediols and 1,3-diketones." Canadian Journal of Chemistry 64, no. 1 (1986): 127–32. http://dx.doi.org/10.1139/v86-022.

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Equations have been derived to describe how the ratio of the total concentration of all keto forms to that of all enolic forms (K′) varies with changing pH, for a tautomeric system in which the enol and ketone are polyprotic acids. The influence of pH on the tautomerism of 2-amino-9,10-anthracenediol, 2,9,10-anthracenetriol, 2,4-pentanedione, and 1-(3-pyridyl)-1,3-butanedione was examined. The equilibrium constants for all the acid–base equilibria involved were calculated from the dependence of K′ on pH.

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6

Holzgrabe, Ulrike, Willy Friedrichsen, and Karl-F. Hesse. "Keto-Enol-Tautomerism and Configurational Isomerism of 2,6-Disubstituted 4-Piperidone-3,5-dicarboxylates." Zeitschrift für Naturforschung B 46, no. 9 (1991): 1237–50. http://dx.doi.org/10.1515/znb-1991-0918.

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The dialkyl 2,6-dialkylsubstituted 4-piperidone-3,5-dicarboxylates were synthesized by a Mannich procedure. Depending on the substitution at the nitrogen keto-enol-tautomerism and a configurational isomerism at C 2 is observed. The structure of the N-substituted piperidone 24 E (C18H29NO5) has been determined by X-ray analysis: it is characterized by an enol structure of the β-ketoester and an axial position of the alkyl group at C 2 and an equatorial one of the alkyl group at C 6. The O–H···O hydrogen bond shows characteristic values of a strong hydrogen bond. The N-unsubstituted piperidones

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7

Mohammed, Sewara J., Akam K. Salih, Mohammad Amin M. Rashid, Khalid M. Omer, and Karzan A. Abdalkarim. "Synthesis, Spectroscopic Studies and Keto-Enol Tautomerism of Novel 1,3,4-Thiadiazole Derivative Containing 3-Mercaptobutan-2-one and Quinazolin-4-one Moieties." Molecules 25, no. 22 (2020): 5441. http://dx.doi.org/10.3390/molecules25225441.

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In this study, a novel 1,3,4-thiadiazole derivative containing 3-mercaptobutan-2-one and quinazolin-4-one moieties (Compound 3) is synthesized by the coupling of 2-amino-1,3,4-thiadiazole-5-(3-mercaptobutan-2-one) (Compound 1) with 2-Phenyl-4H-3,1-benzoxazin-4-one (Compound 2) in one molecule moiety. Compound 3 is found to exist as two types of intra-molecular hydrogen bonding with keto-enol tautomerism characters, which is further confirmed using FTIR, 1H-NMR, 13C-NMR, mass spectrometer, and UV-Visible spectra. The 1H-NMR and UV-Visible spectra of Compound 3 are investigated in different solv

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8

Melánová, Klára, Ludvík Beneš, Vítězslav Zima, Pavla Čapková, and Miroslava Trchová. "Intercalation of Ketones in Vanadyl Phosphate and Isostructural Hosts." Collection of Czechoslovak Chemical Communications 64, no. 12 (1999): 1975–79. http://dx.doi.org/10.1135/cccc19991975.

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The intercalation of acetone and butan-2-one in vanadyl and niobyl phosphates and niobyl arsenate is reported. All intercalates prepared are tetragonal and their basal spacings are close to each other. The intercalates contain one molecule of the ketone per formula unit. The existence of keto-enol tautomerism of guest molecules in interlayer space is assumed.

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9

Rzaev, Zakir M. O., Güneri Akovali, E. Yu Kuliyeva, and N. Yu Lezgiev. "Complex-radical copolymerization of vinylcyclohexyl ketones with maleic anhydride and N-p-tolylmaleimide." Eurasian Chemico-Technological Journal 1, no. 1 (2016): 17. http://dx.doi.org/10.18321/ectj343.

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<p>Some features of the formation and photochemical reactions of cyclohexylketone containing macromolecules including copolymers of vinylcyclohexyl ketone (VCHK) and its derivatives (V-a-Cl-CHK and V- d-C1-CHK) with maleic anhydride (MA) and N-p-tolylmaleimide (TMI) have been revealed. It has been established that keto-enol tautomerism is the only reaction realized in the vinylcyclohexylketone molecules having mobile hydrogen atom at a -position in the cyclohexane ring, enol form of which is formed by charge-transfer complexes with anhydride or imide of maleic acid as acceptor monomers.

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10

Kazmierczak, Jean C., Roberta Cargnelutti, Thiago Barcellos, Claudio C. Silveira та Ricardo F. Schumacher. "Selective synthesis of α-organylthio esters and α-organylthio ketones from β-keto esters and sodium S-organyl sulfurothioates under basic conditions". Beilstein Journal of Organic Chemistry 17 (26 січня 2021): 234–44. http://dx.doi.org/10.3762/bjoc.17.24.

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We described herein a selective method to prepare α-organylthio esters and α-organylthio ketones by the reaction of β-keto esters with sodium S-benzyl sulfurothioate or sodium S-alkyl sulfurothioate (Bunte salts) under basic conditions in toluene as the solvent at 100 °C. When 4 equivalents of a base were used, a series of differently substituted α-thio esters were obtained with up to 90% yield. On the other hand, employing 2 equivalents of a base, α-thio ketones were achieved after 18 h under air. Furthermore, after a shorter reaction time, the isolation of keto–enol tautomers was possible, r

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11

Leis, J. Ramón, M. Elena Peña, and D. Lyn H. Williams. "Involvement of the enol tautomers in the nitrosation of ketones." J. Chem. Soc., Chem. Commun., no. 2 (1987): 45–47. http://dx.doi.org/10.1039/c39870000045.

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12

Klopman, G., and P. Andreozzi. "A quantum mechanical study of the mechanism of the enol-ketone tautomerism." Bulletin des Sociétés Chimiques Belges 88, no. 11 (2010): 875–82. http://dx.doi.org/10.1002/bscb.19790881107.

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13

Leis, J. Ramón, M. Elena Peña, D. Lyn H. Williams, and Simon D. Mawson. "Nitrosation of ketones: clear evidence for the involvement of the enol tautomers." J. Chem. Soc., Perkin Trans. 2, no. 2 (1988): 157–62. http://dx.doi.org/10.1039/p29880000157.

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14

Katritzky, Alan R., Ion Ghiviriga, Daniela C. Oniciu, Rory A. More O'Ferrall та Sinead M. Walsh. "Study of the enol–enaminone tautomerism of α-heterocyclic ketones by deuterium effects on 13C chemical shifts". Journal of the Chemical Society, Perkin Transactions 2, № 12 (1997): 2605–8. http://dx.doi.org/10.1039/a705235i.

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15

Rzayev, Z. M., N. Sh Rasulov, L. V. Medyakova, N. Yu Lezgiyev, E. Yu Kuliyeva, and V. P. Zubov. "Effect of keto-enol tautomerism in complexation and radical copolymerization of vinylcyclohexyl ketones with maleic acid derivatives." Polymer Science U.S.S.R. 29, no. 3 (1987): 540–49. http://dx.doi.org/10.1016/0032-3950(87)90259-0.

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16

Alpegiani, Marco, Pierluigi Bissolino, Daniels Borghi, et al. "Cephem sulfones as inactivators of human leukocyte elastase. II. Keto-enol tautomerish in cephem-4-ketones." Bioorganic & Medicinal Chemistry Letters 2, no. 9 (1992): 1127–32. http://dx.doi.org/10.1016/s0960-894x(00)80632-0.

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17

KATRITZKY, A. R., I. GHIVIRIGA, D. C. ONICIU, R. A. M. O'FERRALL та S. M. WALSH. "ChemInform Abstract: Study of the Enol-Enaminone Tautomerism of α-Heterocyclic Ketones by Deuterium Effects on 13C Chemical Shifts." ChemInform 29, № 13 (2010): no. http://dx.doi.org/10.1002/chin.199813037.

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18

O'Ferrall, Rory A. More, та Brian A. Murray. "1H and13C NMR spectra of α-heterocyclic ketones and assignment of keto, enol and enaminone tautomeric structures". J. Chem. Soc., Perkin Trans. 2, № 12 (1994): 2461–70. http://dx.doi.org/10.1039/p29940002461.

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19

Duus, F. ".beta.-Thioxo ketones. Part 12. The enol-enethiol tautomerism of simple nonaromatic .beta.-thioxo ketones. An approach to quantitative description based upon proton NMR and UV spectral parameters and the adaptation of these into a simplified model of the tautomeric equilibrium." Journal of the American Chemical Society 108, no. 4 (1986): 630–38. http://dx.doi.org/10.1021/ja00264a012.

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20

Bustelo, Emilio, Manuel Jiménez-Tenorio, M. Carmen Puerta та Pedro Valerga. "Ruthenium Allenylidene/Alkenylcarbyne Complexes Triggering Keto−Enol Tautomerism: An Alternative Approach to γ-Keto Vinylidenes from Simple Ketones and 1,3-Dicarbonyl Compounds". Organometallics 25, № 16 (2006): 4019–25. http://dx.doi.org/10.1021/om060453y.

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21

MORE O'FERRALL, R. A., та B. A. MURRAY. "ChemInform Abstract: 1H and 13C NMR Spectra of α-Heterocyclic Ketones and Assignment of Keto, Enol and Enaminone Tautomeric Structures." ChemInform 26, № 19 (2010): no. http://dx.doi.org/10.1002/chin.199519029.

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22

Holloway, Anne-Louise, Jack Treacy, Howard Sidebottom, et al. "Rate coefficients for the reactions of OH radicals with the keto/enol tautomers of 2,4-pentanedione and 3-methyl-2,4-pentanedione, allyl alcohol and methyl vinyl ketone using the enols and methyl nitrite as photolytic sources of OH." Journal of Photochemistry and Photobiology A: Chemistry 176, no. 1-3 (2005): 183–90. http://dx.doi.org/10.1016/j.jphotochem.2005.08.031.

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23

Wang, Dan, Xinyu Zhang, Xiangdong Han, et al. "Ketone–enol tautomerism, polymorphism, mechanofluorochromism and solid-state acidochromism of isoquinolinone–arylidenehydrazine derivatives." Journal of Materials Chemistry C, 2021. http://dx.doi.org/10.1039/d1tc03063a.

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24

DUUS, F. "ChemInform Abstract: β-Thioxo Ketones. Part 12. The Enol-Enethiol Tautomerism of Simple Nonaromatic β-Thioxo Ketones." Chemischer Informationsdienst 17, № 25 (1986). http://dx.doi.org/10.1002/chin.198625087.

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25

LEIS, J. R., M. E. PENA, D. L. H. WILLIAMS, and S. D. MAWSON. "ChemInform Abstract: Nitrosation of Ketones (I)-(III): Clear Evidence for the Involvement of the Enol Tautomers." ChemInform 19, no. 19 (1988). http://dx.doi.org/10.1002/chin.198819109.

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