КРИСТАЛІЧНА БУДОВА І ТАУТОМЕРІЯ У РОЗЧИНАХ АЛКІЛАМІНО-β-КЕТОЄНОЛІВ**
The structure of alkylamino-β-ketoenols obtained by opening of the pyran cycle of chalcones based on dehydracetic acid was studied by X-ray diffraction, IR, 1H NMR spectroscopy and chromatography-mass spectrometry. The infrared spectra of the compounds appear to be typical of β-ketoenols. The crysta...
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| Date: | 2019 |
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V.I.Vernadsky Institute of General and Inorganic Chemistry
2019
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| Online Access: | https://ucj.org.ua/index.php/journal/article/view/73 |
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Ukrainian Chemistry Journal |
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2019-10-02T11:30:42Z |
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English |
| topic |
дегідрацетова кислота халкони алкіламіно-β-кетоєноли. |
| spellingShingle |
дегідрацетова кислота халкони алкіламіно-β-кетоєноли. CHERNII, VIKTOR КРИСТАЛІЧНА БУДОВА І ТАУТОМЕРІЯ У РОЗЧИНАХ АЛКІЛАМІНО-β-КЕТОЄНОЛІВ** |
| topic_facet |
dehydracetic acid chalcones alkylamino-β-ketoenols. дегидрацетовая кислота халконы алкиламино-β-кетоенолы. дегідрацетова кислота халкони алкіламіно-β-кетоєноли. |
| format |
Article |
| author |
CHERNII, VIKTOR |
| author_facet |
CHERNII, VIKTOR |
| author_sort |
CHERNII, VIKTOR |
| title |
КРИСТАЛІЧНА БУДОВА І ТАУТОМЕРІЯ У РОЗЧИНАХ АЛКІЛАМІНО-β-КЕТОЄНОЛІВ** |
| title_short |
КРИСТАЛІЧНА БУДОВА І ТАУТОМЕРІЯ У РОЗЧИНАХ АЛКІЛАМІНО-β-КЕТОЄНОЛІВ** |
| title_full |
КРИСТАЛІЧНА БУДОВА І ТАУТОМЕРІЯ У РОЗЧИНАХ АЛКІЛАМІНО-β-КЕТОЄНОЛІВ** |
| title_fullStr |
КРИСТАЛІЧНА БУДОВА І ТАУТОМЕРІЯ У РОЗЧИНАХ АЛКІЛАМІНО-β-КЕТОЄНОЛІВ** |
| title_full_unstemmed |
КРИСТАЛІЧНА БУДОВА І ТАУТОМЕРІЯ У РОЗЧИНАХ АЛКІЛАМІНО-β-КЕТОЄНОЛІВ** |
| title_sort |
кристалічна будова і таутомерія у розчинах алкіламіно-β-кетоєнолів** |
| title_alt |
CRYSTAL STRUCTURE AND TAUTOMERISM OF ALKYLAMINO-β-KETOENOLS IN SOLUTIONS КРИСТАЛЛИЧЕСКОЕ СТРОЕНИЕ И ТАУТОМЕРИЯ В РАСТВОРАХ АЛКИЛАМИНО-β-КЕТОЕНОЛОВ |
| description |
The structure of alkylamino-β-ketoenols obtained by opening of the pyran cycle of chalcones based on dehydracetic acid was studied by X-ray diffraction, IR, 1H NMR spectroscopy and chromatography-mass spectrometry. The infrared spectra of the compounds appear to be typical of β-ketoenols. The crystalline structure (2Z,5Z,7E,9E)-6-hydroxy-2-(methylami-no)-10-phenylethoxy-2,5,7,9-tetraene-4-one was first determined. A comparative analysis of it with 2 pre-viously published structures has been carried out. All of these compounds are crystallized in the form of yellow plates in the monoclinic crystalline system (spatial group P21/n), they have a planar arrangement of the polyene chain and β-ketoenol fragment con-jugated to the aromatic ring. It has been established that the planar configuration of the β-ketoenol fragment is stabilized by hydrogen bonds between the hydroxy and keto group and the amino and keto group in the crystalline state. The length of the polymethine chain, the nature of the substituents in the aromatic and aliphatic part of the molecule do not significantly affect the size and geometry of the alkylamino-β-ketoenolate fragment. Approximately the same lengths of bonds, the distance between atoms and the corners indicate that all these com-pounds may have similar chelating properties. Ac-cording to 1H NMR spectroscopy in various deu-terated solvents (benzene, DMSO, chloroform, ace-tone, methanol and trifluoroacetic acid), most of the main signals of the obtained compounds have sa-tellites, which indicates the existence of several isomeric forms in solutions. The analysis of integral intensities of labile protons in 1H NMR spectra does not allow to obtain accurate results regarding the ratio of tautomers in a solution, but for a series of compounds their approximate ratio in chloroform, DMSO and trifluoroacetic acid have been established (from 70:30 in CDCl3 to 90:10 in DMSO and CF3CO2D). The stability of the tautomers in the solutions is confirmed by the data of chromatogra-phy-mass spectrometry. |
| publisher |
V.I.Vernadsky Institute of General and Inorganic Chemistry |
| publishDate |
2019 |
| url |
https://ucj.org.ua/index.php/journal/article/view/73 |
| work_keys_str_mv |
AT cherniiviktor crystalstructureandtautomerismofalkylaminobketoenolsinsolutions AT cherniiviktor kristalličeskoestroenieitautomeriâvrastvorahalkilaminobketoenolov AT cherniiviktor kristalíčnabudovaítautomeríâurozčinahalkílamínobketoênolív |
| first_indexed |
2025-09-24T17:43:31Z |
| last_indexed |
2025-09-24T17:43:31Z |
| _version_ |
1849658081185628160 |
| spelling |
oai:ojs2.1444248.nisspano.web.hosting-test.net:article-732019-10-02T11:30:42Z CRYSTAL STRUCTURE AND TAUTOMERISM OF ALKYLAMINO-β-KETOENOLS IN SOLUTIONS КРИСТАЛЛИЧЕСКОЕ СТРОЕНИЕ И ТАУТОМЕРИЯ В РАСТВОРАХ АЛКИЛАМИНО-β-КЕТОЕНОЛОВ КРИСТАЛІЧНА БУДОВА І ТАУТОМЕРІЯ У РОЗЧИНАХ АЛКІЛАМІНО-β-КЕТОЄНОЛІВ** CHERNII, VIKTOR dehydracetic acid, chalcones, alkylamino-β-ketoenols. дегидрацетовая кислота, халконы, алкиламино-β-кетоенолы. дегідрацетова кислота, халкони, алкіламіно-β-кетоєноли. The structure of alkylamino-β-ketoenols obtained by opening of the pyran cycle of chalcones based on dehydracetic acid was studied by X-ray diffraction, IR, 1H NMR spectroscopy and chromatography-mass spectrometry. The infrared spectra of the compounds appear to be typical of β-ketoenols. The crystalline structure (2Z,5Z,7E,9E)-6-hydroxy-2-(methylami-no)-10-phenylethoxy-2,5,7,9-tetraene-4-one was first determined. A comparative analysis of it with 2 pre-viously published structures has been carried out. All of these compounds are crystallized in the form of yellow plates in the monoclinic crystalline system (spatial group P21/n), they have a planar arrangement of the polyene chain and β-ketoenol fragment con-jugated to the aromatic ring. It has been established that the planar configuration of the β-ketoenol fragment is stabilized by hydrogen bonds between the hydroxy and keto group and the amino and keto group in the crystalline state. The length of the polymethine chain, the nature of the substituents in the aromatic and aliphatic part of the molecule do not significantly affect the size and geometry of the alkylamino-β-ketoenolate fragment. Approximately the same lengths of bonds, the distance between atoms and the corners indicate that all these com-pounds may have similar chelating properties. Ac-cording to 1H NMR spectroscopy in various deu-terated solvents (benzene, DMSO, chloroform, ace-tone, methanol and trifluoroacetic acid), most of the main signals of the obtained compounds have sa-tellites, which indicates the existence of several isomeric forms in solutions. The analysis of integral intensities of labile protons in 1H NMR spectra does not allow to obtain accurate results regarding the ratio of tautomers in a solution, but for a series of compounds their approximate ratio in chloroform, DMSO and trifluoroacetic acid have been established (from 70:30 in CDCl3 to 90:10 in DMSO and CF3CO2D). The stability of the tautomers in the solutions is confirmed by the data of chromatogra-phy-mass spectrometry. The structure of alkylamino-β-ketoenols obtained by opening of the pyran cycle of chalcones based on dehydracetic acid was studied by X-ray diffraction, IR, 1H NMR spectroscopy and chromatography-mass spectrometry. The infrared spectra of the compounds appear to be typical of β-ketoenols. The crystalline structure (2Z,5Z,7E,9E)-6-hydroxy-2-(methylami-no)-10-phenylethoxy-2,5,7,9-tetraene-4-one was first determined. A comparative analysis of it with 2 pre-viously published structures has been carried out. All of these compounds are crystallized in the form of yellow plates in the monoclinic crystalline system (spatial group P21/n), they have a planar arrangement of the polyene chain and β-ketoenol fragment con-jugated to the aromatic ring. It has been established that the planar configuration of the β-ketoenol fragment is stabilized by hydrogen bonds between the hydroxy and keto group and the amino and keto group in the crystalline state. The length of the polymethine chain, the nature of the substituents in the aromatic and aliphatic part of the molecule do not significantly affect the size and geometry of the alkylamino-β-ketoenolate fragment. Approximately the same lengths of bonds, the distance between atoms and the corners indicate that all these com-pounds may have similar chelating properties. Ac-cording to 1H NMR spectroscopy in various deu-terated solvents (benzene, DMSO, chloroform, ace-tone, methanol and trifluoroacetic acid), most of the main signals of the obtained compounds have sa-tellites, which indicates the existence of several isomeric forms in solutions. The analysis of integral intensities of labile protons in 1H NMR spectra does not allow to obtain accurate results regarding the ratio of tautomers in a solution, but for a series of compounds their approximate ratio in chloroform, DMSO and trifluoroacetic acid have been established (from 70:30 in CDCl3 to 90:10 in DMSO and CF3CO2D). The stability of the tautomers in the solutions is confirmed by the data of chromatogra-phy-mass spectrometry. The structure of alkylamino-β-ketoenols obtained by opening of the pyran cycle of chalcones based on dehydracetic acid was studied by X-ray diffraction, IR, 1H NMR spectroscopy and chromatography-mass spectrometry. The infrared spectra of the compounds appear to be typical of β-ketoenols. The crystalline structure (2Z,5Z,7E,9E)-6-hydroxy-2-(methylami-no)-10-phenylethoxy-2,5,7,9-tetraene-4-one was first determined. A comparative analysis of it with 2 pre-viously published structures has been carried out. All of these compounds are crystallized in the form of yellow plates in the monoclinic crystalline system (spatial group P21/n), they have a planar arrangement of the polyene chain and β-ketoenol fragment con-jugated to the aromatic ring. It has been established that the planar configuration of the β-ketoenol fragment is stabilized by hydrogen bonds between the hydroxy and keto group and the amino and keto group in the crystalline state. The length of the polymethine chain, the nature of the substituents in the aromatic and aliphatic part of the molecule do not significantly affect the size and geometry of the alkylamino-β-ketoenolate fragment. Approximately the same lengths of bonds, the distance between atoms and the corners indicate that all these com-pounds may have similar chelating properties. Ac-cording to 1H NMR spectroscopy in various deu-terated solvents (benzene, DMSO, chloroform, ace-tone, methanol and trifluoroacetic acid), most of the main signals of the obtained compounds have sa-tellites, which indicates the existence of several isomeric forms in solutions. The analysis of integral intensities of labile protons in 1H NMR spectra does not allow to obtain accurate results regarding the ratio of tautomers in a solution, but for a series of compounds their approximate ratio in chloroform, DMSO and trifluoroacetic acid have been established (from 70:30 in CDCl3 to 90:10 in DMSO and CF3CO2D). The stability of the tautomers in the solutions is confirmed by the data of chromatogra-phy-mass spectrometry. V.I.Vernadsky Institute of General and Inorganic Chemistry 2019-08-15 Article Article Inorganic Chemistry Неорганическая химия Неорганічна хімія application/pdf https://ucj.org.ua/index.php/journal/article/view/73 10.33609/0041-6045.85.8.2019.73-82 Ukrainian Chemistry Journal; Vol. 85 No. 8 (2019): Ukrainian Chemistry Journal; 73-82 Украинский химический журнал; Том 85 № 8 (2019): Украинский химический журнал; 73-82 Український хімічний журнал; Том 85 № 8 (2019): Український хімічний журнал; 73-82 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/73/48 |