Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations
Tetrazolium-5-aminides have been prepared by the tert-butylation of 5-aminotetrazole and its N-methyl derivatives by the t-BuOH/HClO4 system followed by the treatment of the tetrazolium salts by alkali. The mesoionic compounds have been found to show a higher reactivity of the exocyclic N atom in co...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2021-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.17.34 |
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| author | Vladislav A. Budevich Sergei V. Voitekhovich Alexander V. Zuraev Vadim E. Matulis Vitaly E. Matulis Alexander S. Lyakhov Ludmila S. Ivashkevich Oleg A. Ivashkevich |
| author_facet | Vladislav A. Budevich Sergei V. Voitekhovich Alexander V. Zuraev Vadim E. Matulis Vitaly E. Matulis Alexander S. Lyakhov Ludmila S. Ivashkevich Oleg A. Ivashkevich |
| author_sort | Vladislav A. Budevich |
| collection | DOAJ |
| description | Tetrazolium-5-aminides have been prepared by the tert-butylation of 5-aminotetrazole and its N-methyl derivatives by the t-BuOH/HClO4 system followed by the treatment of the tetrazolium salts by alkali. The mesoionic compounds have been found to show a higher reactivity of the exocyclic N atom in comparison with 5-aminotetrazoles. The compounds reacted with 1,2-dibromoethane and 5-(methylsulfonyl)-1-phenyl-1H-tetrazole with substitution of bromine and methylsulfonyl groups giving the corresponding tetrazolium salts or conjugate aminides. The obtained mesoionic tetrazoles have been characterized by elemental analysis, FTIR, NMR, and UV–vis spectroscopy, TGA/DSC analysis and for 1,3-di-tert-butyltetrazolium-5-aminide, its N,N’-ethylene-bridged bis-derivative and (1,3-di-tert-butyl-1H-tetrazol-3-ium-5-yl)(1-phenyl-1H-tetrazol-5-yl)amide by single crystal X-ray analysis. The structural and spectral features of the tetrazolium-5-aminides are discussed by using quantum-chemical calculations. |
| first_indexed | 2024-12-14T17:34:47Z |
| format | Article |
| id | doaj.art-4aaefbff75a74d36af0b57beed206cbc |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T17:34:47Z |
| publishDate | 2021-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-4aaefbff75a74d36af0b57beed206cbc2022-12-21T22:53:01ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-02-0117138539510.3762/bjoc.17.341860-5397-17-34Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculationsVladislav A. Budevich0Sergei V. Voitekhovich1Alexander V. Zuraev2Vadim E. Matulis3Vitaly E. Matulis4Alexander S. Lyakhov5Ludmila S. Ivashkevich6Oleg A. Ivashkevich7Laboratory for chemistry of condensed systems, Research Institute for Physical Chemical Problems of Belarusian State University, Leningradskaya 14, 220006 Minsk, Republic of BelarusLaboratory for chemistry of condensed systems, Research Institute for Physical Chemical Problems of Belarusian State University, Leningradskaya 14, 220006 Minsk, Republic of BelarusLaboratory for chemistry of condensed systems, Research Institute for Physical Chemical Problems of Belarusian State University, Leningradskaya 14, 220006 Minsk, Republic of BelarusLaboratory for chemistry of condensed systems, Research Institute for Physical Chemical Problems of Belarusian State University, Leningradskaya 14, 220006 Minsk, Republic of BelarusLaboratory for chemistry of condensed systems, Research Institute for Physical Chemical Problems of Belarusian State University, Leningradskaya 14, 220006 Minsk, Republic of BelarusLaboratory for chemistry of condensed systems, Research Institute for Physical Chemical Problems of Belarusian State University, Leningradskaya 14, 220006 Minsk, Republic of BelarusLaboratory for chemistry of condensed systems, Research Institute for Physical Chemical Problems of Belarusian State University, Leningradskaya 14, 220006 Minsk, Republic of BelarusLaboratory for chemistry of condensed systems, Research Institute for Physical Chemical Problems of Belarusian State University, Leningradskaya 14, 220006 Minsk, Republic of BelarusTetrazolium-5-aminides have been prepared by the tert-butylation of 5-aminotetrazole and its N-methyl derivatives by the t-BuOH/HClO4 system followed by the treatment of the tetrazolium salts by alkali. The mesoionic compounds have been found to show a higher reactivity of the exocyclic N atom in comparison with 5-aminotetrazoles. The compounds reacted with 1,2-dibromoethane and 5-(methylsulfonyl)-1-phenyl-1H-tetrazole with substitution of bromine and methylsulfonyl groups giving the corresponding tetrazolium salts or conjugate aminides. The obtained mesoionic tetrazoles have been characterized by elemental analysis, FTIR, NMR, and UV–vis spectroscopy, TGA/DSC analysis and for 1,3-di-tert-butyltetrazolium-5-aminide, its N,N’-ethylene-bridged bis-derivative and (1,3-di-tert-butyl-1H-tetrazol-3-ium-5-yl)(1-phenyl-1H-tetrazol-5-yl)amide by single crystal X-ray analysis. The structural and spectral features of the tetrazolium-5-aminides are discussed by using quantum-chemical calculations.https://doi.org/10.3762/bjoc.17.34aminotetrazolesdftmesoionic compoundsuv–vis spectrax-ray analysis |
| spellingShingle | Vladislav A. Budevich Sergei V. Voitekhovich Alexander V. Zuraev Vadim E. Matulis Vitaly E. Matulis Alexander S. Lyakhov Ludmila S. Ivashkevich Oleg A. Ivashkevich Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations Beilstein Journal of Organic Chemistry aminotetrazoles dft mesoionic compounds uv–vis spectra x-ray analysis |
| title | Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations |
| title_full | Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations |
| title_fullStr | Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations |
| title_full_unstemmed | Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations |
| title_short | Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations |
| title_sort | mesoionic tetrazolium 5 aminides synthesis molecular and crystal structures uv vis spectra and dft calculations |
| topic | aminotetrazoles dft mesoionic compounds uv–vis spectra x-ray analysis |
| url | https://doi.org/10.3762/bjoc.17.34 |
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