Assignment of NMR spectral data of diastereomeric tetrahydrofuranyl acetals directly from their mixture by spectral simulation
In this study, an NMR spectral analysis of the mixture of diastereomeric acetals, synthesized from 2,3-dihydrofurane and a racemic mixture of citronellol, was performed. 1H-NMR full spin analysis was achieved by manually adjusting δH and J values (previously calculated using the Spartan software) to...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2024-01-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | https://doiserbia.nb.rs/img/doi/0352-5139/2024/0352-51392300054N.pdf |
| _version_ | 1797215522234826752 |
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| author | Nešić Milan S. Nešić Milica D. Radulović Niko S. |
| author_facet | Nešić Milan S. Nešić Milica D. Radulović Niko S. |
| author_sort | Nešić Milan S. |
| collection | DOAJ |
| description | In this study, an NMR spectral analysis of the mixture of diastereomeric acetals, synthesized from 2,3-dihydrofurane and a racemic mixture of citronellol, was performed. 1H-NMR full spin analysis was achieved by manually adjusting δH and J values (previously calculated using the Spartan software) to fit the experimentally available values, followed by further optimization using MestreNova software. The simulated 1H- and 13C-NMR spectra of individual diastereomers, as well as their superimposed and summed spectra, were compared with the obtained experimental spectra. Spin simulation of proton signals was particularly useful for the assignment of the diastereotopic protons of tetrahydrofuranyl moiety and diastereomer discrimination. The NMR spectral data of individual diastereomers – chemical shifts, coupling constants, HMBC and NOESY interactions were systematized in appropriate tables and schemes. To the best of our knowledge, this is for the first time that the complete assignment of tetrahydrofuranyl moiety was performed, and the data obtained herein may be of great importance for the utilization of this protecting group in the future. |
| first_indexed | 2024-04-24T11:31:24Z |
| format | Article |
| id | doaj.art-d1e0d84cd9974220918a485fdf432bc7 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-04-24T11:31:24Z |
| publishDate | 2024-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-d1e0d84cd9974220918a485fdf432bc72024-04-10T10:17:14ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212024-01-0189111110.2298/JSC230614054N0352-51392300054NAssignment of NMR spectral data of diastereomeric tetrahydrofuranyl acetals directly from their mixture by spectral simulationNešić Milan S.0Nešić Milica D.1https://orcid.org/0000-0003-3294-3444Radulović Niko S.2https://orcid.org/0000-0003-1342-7567Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Niš, SerbiaDepartment of Chemistry, Faculty of Science and Mathematics, University of Niš, Niš, SerbiaDepartment of Chemistry, Faculty of Science and Mathematics, University of Niš, Niš, SerbiaIn this study, an NMR spectral analysis of the mixture of diastereomeric acetals, synthesized from 2,3-dihydrofurane and a racemic mixture of citronellol, was performed. 1H-NMR full spin analysis was achieved by manually adjusting δH and J values (previously calculated using the Spartan software) to fit the experimentally available values, followed by further optimization using MestreNova software. The simulated 1H- and 13C-NMR spectra of individual diastereomers, as well as their superimposed and summed spectra, were compared with the obtained experimental spectra. Spin simulation of proton signals was particularly useful for the assignment of the diastereotopic protons of tetrahydrofuranyl moiety and diastereomer discrimination. The NMR spectral data of individual diastereomers – chemical shifts, coupling constants, HMBC and NOESY interactions were systematized in appropriate tables and schemes. To the best of our knowledge, this is for the first time that the complete assignment of tetrahydrofuranyl moiety was performed, and the data obtained herein may be of great importance for the utilization of this protecting group in the future.https://doiserbia.nb.rs/img/doi/0352-5139/2024/0352-51392300054N.pdftetrahydrofurancitronellolspectral assignmentspin simulationdiastereomersmixture |
| spellingShingle | Nešić Milan S. Nešić Milica D. Radulović Niko S. Assignment of NMR spectral data of diastereomeric tetrahydrofuranyl acetals directly from their mixture by spectral simulation Journal of the Serbian Chemical Society tetrahydrofuran citronellol spectral assignment spin simulation diastereomers mixture |
| title | Assignment of NMR spectral data of diastereomeric tetrahydrofuranyl acetals directly from their mixture by spectral simulation |
| title_full | Assignment of NMR spectral data of diastereomeric tetrahydrofuranyl acetals directly from their mixture by spectral simulation |
| title_fullStr | Assignment of NMR spectral data of diastereomeric tetrahydrofuranyl acetals directly from their mixture by spectral simulation |
| title_full_unstemmed | Assignment of NMR spectral data of diastereomeric tetrahydrofuranyl acetals directly from their mixture by spectral simulation |
| title_short | Assignment of NMR spectral data of diastereomeric tetrahydrofuranyl acetals directly from their mixture by spectral simulation |
| title_sort | assignment of nmr spectral data of diastereomeric tetrahydrofuranyl acetals directly from their mixture by spectral simulation |
| topic | tetrahydrofuran citronellol spectral assignment spin simulation diastereomers mixture |
| url | https://doiserbia.nb.rs/img/doi/0352-5139/2024/0352-51392300054N.pdf |
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