The Study of Structural Features of N- and O-Derivatives of 4,5-Dihydroxyimidazolidine-2-Thione by NMR Spectroscopy and Quantum Chemical Calculations
In the present work, the new N-methylol and O-alkyl derivatives of 4,5-dihydroxyimidazolidine-2-thione (DHIT) are synthesized. The effects of N-alkyl, N-phenyl, N-methylol, and O-alkyl substituents of DHIT on the <sup>13</sup>C and <sup>1</sup>H signals in NMR spectra of the...
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| Format: | Article |
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MDPI AG
2022-12-01
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| Series: | Magnetochemistry |
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| Online Access: | https://www.mdpi.com/2312-7481/9/1/15 |
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| author | Liudmila E. Kalichkina Alexander V. Fateev Polina K. Krivolapenko Kristina A. Isakova Alexey S. Knyazev Victor S. Malkov Abdigali A. Bakibaev Vera P. Tuguldurova |
| author_facet | Liudmila E. Kalichkina Alexander V. Fateev Polina K. Krivolapenko Kristina A. Isakova Alexey S. Knyazev Victor S. Malkov Abdigali A. Bakibaev Vera P. Tuguldurova |
| author_sort | Liudmila E. Kalichkina |
| collection | DOAJ |
| description | In the present work, the new N-methylol and O-alkyl derivatives of 4,5-dihydroxyimidazolidine-2-thione (DHIT) are synthesized. The effects of N-alkyl, N-phenyl, N-methylol, and O-alkyl substituents of DHIT on the <sup>13</sup>C and <sup>1</sup>H signals in NMR spectra of the imidazolidine-2-thione ring are systematized using quantum chemical calculations. The shift values of carbon and hydrogen atoms are specific for the geometric isomers of the indicated DHIT derivatives. The chemical shifts of the carbon atoms of the methine groups allows for identifying the cis and trans isomers of the N-alkyl derivatives of DHIT due to the up-field shifts of the cis isomers. The introduction of an alkyl substituent at the N-position of the imidazolidine-2-thione ring leads to the up-field shifts of the carbon atoms of the ring due to the inductive effects of these groups. The ring current effect in the N-phenyl derivatives of DHIT that affects the positions of the carbon signals of the imidazolidine-2-thione ring has been found. The N-methylol derivatives of 4,5-dihydroxyimidazolidine-2-thione have been identified for the first time using 1D and 2D NMR. |
| first_indexed | 2024-03-09T11:52:36Z |
| format | Article |
| id | doaj.art-89ac8ca96e7243ff8ca9a8ade1fbfb97 |
| institution | Directory Open Access Journal |
| issn | 2312-7481 |
| language | English |
| last_indexed | 2024-03-09T11:52:36Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Magnetochemistry |
| spelling | doaj.art-89ac8ca96e7243ff8ca9a8ade1fbfb972023-11-30T23:12:49ZengMDPI AGMagnetochemistry2312-74812022-12-01911510.3390/magnetochemistry9010015The Study of Structural Features of N- and O-Derivatives of 4,5-Dihydroxyimidazolidine-2-Thione by NMR Spectroscopy and Quantum Chemical CalculationsLiudmila E. Kalichkina0Alexander V. Fateev1Polina K. Krivolapenko2Kristina A. Isakova3Alexey S. Knyazev4Victor S. Malkov5Abdigali A. Bakibaev6Vera P. Tuguldurova7Faculty of Chemistry, Tomsk State University, 36, Lenin Avenue, Tomsk 634050, RussiaFaculty of Chemistry, Tomsk State University, 36, Lenin Avenue, Tomsk 634050, RussiaFaculty of Chemistry, Tomsk State University, 36, Lenin Avenue, Tomsk 634050, RussiaFaculty of Chemistry, Tomsk State University, 36, Lenin Avenue, Tomsk 634050, RussiaFaculty of Chemistry, Tomsk State University, 36, Lenin Avenue, Tomsk 634050, RussiaFaculty of Chemistry, Tomsk State University, 36, Lenin Avenue, Tomsk 634050, RussiaFaculty of Chemistry, Tomsk State University, 36, Lenin Avenue, Tomsk 634050, RussiaFaculty of Chemistry, Tomsk State University, 36, Lenin Avenue, Tomsk 634050, RussiaIn the present work, the new N-methylol and O-alkyl derivatives of 4,5-dihydroxyimidazolidine-2-thione (DHIT) are synthesized. The effects of N-alkyl, N-phenyl, N-methylol, and O-alkyl substituents of DHIT on the <sup>13</sup>C and <sup>1</sup>H signals in NMR spectra of the imidazolidine-2-thione ring are systematized using quantum chemical calculations. The shift values of carbon and hydrogen atoms are specific for the geometric isomers of the indicated DHIT derivatives. The chemical shifts of the carbon atoms of the methine groups allows for identifying the cis and trans isomers of the N-alkyl derivatives of DHIT due to the up-field shifts of the cis isomers. The introduction of an alkyl substituent at the N-position of the imidazolidine-2-thione ring leads to the up-field shifts of the carbon atoms of the ring due to the inductive effects of these groups. The ring current effect in the N-phenyl derivatives of DHIT that affects the positions of the carbon signals of the imidazolidine-2-thione ring has been found. The N-methylol derivatives of 4,5-dihydroxyimidazolidine-2-thione have been identified for the first time using 1D and 2D NMR.https://www.mdpi.com/2312-7481/9/1/154,5-dihydroxyimidazolidine-2-thioneN-alkyl derivativesO-alkyl derivativesN-methylol derivativesNMR spectroscopyquantum chemical calculations |
| spellingShingle | Liudmila E. Kalichkina Alexander V. Fateev Polina K. Krivolapenko Kristina A. Isakova Alexey S. Knyazev Victor S. Malkov Abdigali A. Bakibaev Vera P. Tuguldurova The Study of Structural Features of N- and O-Derivatives of 4,5-Dihydroxyimidazolidine-2-Thione by NMR Spectroscopy and Quantum Chemical Calculations Magnetochemistry 4,5-dihydroxyimidazolidine-2-thione N-alkyl derivatives O-alkyl derivatives N-methylol derivatives NMR spectroscopy quantum chemical calculations |
| title | The Study of Structural Features of N- and O-Derivatives of 4,5-Dihydroxyimidazolidine-2-Thione by NMR Spectroscopy and Quantum Chemical Calculations |
| title_full | The Study of Structural Features of N- and O-Derivatives of 4,5-Dihydroxyimidazolidine-2-Thione by NMR Spectroscopy and Quantum Chemical Calculations |
| title_fullStr | The Study of Structural Features of N- and O-Derivatives of 4,5-Dihydroxyimidazolidine-2-Thione by NMR Spectroscopy and Quantum Chemical Calculations |
| title_full_unstemmed | The Study of Structural Features of N- and O-Derivatives of 4,5-Dihydroxyimidazolidine-2-Thione by NMR Spectroscopy and Quantum Chemical Calculations |
| title_short | The Study of Structural Features of N- and O-Derivatives of 4,5-Dihydroxyimidazolidine-2-Thione by NMR Spectroscopy and Quantum Chemical Calculations |
| title_sort | study of structural features of n and o derivatives of 4 5 dihydroxyimidazolidine 2 thione by nmr spectroscopy and quantum chemical calculations |
| topic | 4,5-dihydroxyimidazolidine-2-thione N-alkyl derivatives O-alkyl derivatives N-methylol derivatives NMR spectroscopy quantum chemical calculations |
| url | https://www.mdpi.com/2312-7481/9/1/15 |
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