The Search for the Optimal Methodology for Predicting Fluorinated Cathinone Drugs NMR Chemical Shifts
Cathinone and its synthetic derivatives belong to organic compounds with narcotic properties. Their structural diversity and massive illegal use create the need to develop new analytical methods for their identification in different matrices. NMR spectroscopy is one of the most versatile methods for...
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MDPI AG
2024-12-01
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| author | Natalina Makieieva Teobald Kupka Oimahmad Rahmonov |
| author_facet | Natalina Makieieva Teobald Kupka Oimahmad Rahmonov |
| author_sort | Natalina Makieieva |
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| description | Cathinone and its synthetic derivatives belong to organic compounds with narcotic properties. Their structural diversity and massive illegal use create the need to develop new analytical methods for their identification in different matrices. NMR spectroscopy is one of the most versatile methods for identifying the structure of organic substances. However, its use could sometimes be very difficult and time-consuming due to the complexity of NMR spectra, as well as the technical limitations of measurements. In such cases, molecular modeling serves as a good supporting technique for interpreting ambiguous spectral data. Theoretical prediction of NMR spectra includes calculation of nuclear magnetic shieldings and sometimes also indirect spin–spin coupling constants (SSCC). The quality of theoretical prediction is strongly dependent on the choice of the theory level. In the current study, cathinone and its 12 fluorinated derivatives were selected for gauge-including atomic orbital (GIAO) NMR calculations using Hartree–Fock (HF) and 28 density functionals combined with 6-311++G** basis set to find the optimal level of theory for <sup>1</sup>H, <sup>13</sup>C, and <sup>19</sup>F chemical shifts modeling. All calculations were performed in the gas phase, and solutions were modeled with a polarized-continuum model (PCM) and solvation model based on density (SMD). The results were critically compared with available experimental data. |
| format | Article |
| id | doaj-art-2b3300efc77d4c4d92301d5173a1144b |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-2b3300efc77d4c4d92301d5173a1144b2025-01-10T13:18:44ZengMDPI AGMolecules1420-30492024-12-013015410.3390/molecules30010054The Search for the Optimal Methodology for Predicting Fluorinated Cathinone Drugs NMR Chemical ShiftsNatalina Makieieva0Teobald Kupka1Oimahmad Rahmonov2Faculty of Chemistry and Pharmacy, University of Opole, 48, Oleska Str., 45-052 Opole, PolandFaculty of Chemistry and Pharmacy, University of Opole, 48, Oleska Str., 45-052 Opole, PolandInstitute of Earth Sciences, Faculty of Natural Sciences, University of Silesia in Katowice, 60, Będzińska, 41-200 Sosnowiec, PolandCathinone and its synthetic derivatives belong to organic compounds with narcotic properties. Their structural diversity and massive illegal use create the need to develop new analytical methods for their identification in different matrices. NMR spectroscopy is one of the most versatile methods for identifying the structure of organic substances. However, its use could sometimes be very difficult and time-consuming due to the complexity of NMR spectra, as well as the technical limitations of measurements. In such cases, molecular modeling serves as a good supporting technique for interpreting ambiguous spectral data. Theoretical prediction of NMR spectra includes calculation of nuclear magnetic shieldings and sometimes also indirect spin–spin coupling constants (SSCC). The quality of theoretical prediction is strongly dependent on the choice of the theory level. In the current study, cathinone and its 12 fluorinated derivatives were selected for gauge-including atomic orbital (GIAO) NMR calculations using Hartree–Fock (HF) and 28 density functionals combined with 6-311++G** basis set to find the optimal level of theory for <sup>1</sup>H, <sup>13</sup>C, and <sup>19</sup>F chemical shifts modeling. All calculations were performed in the gas phase, and solutions were modeled with a polarized-continuum model (PCM) and solvation model based on density (SMD). The results were critically compared with available experimental data.https://www.mdpi.com/1420-3049/30/1/54cathinonefluorinated cathinone derivativesDFTGIAO NMR |
| spellingShingle | Natalina Makieieva Teobald Kupka Oimahmad Rahmonov The Search for the Optimal Methodology for Predicting Fluorinated Cathinone Drugs NMR Chemical Shifts Molecules cathinone fluorinated cathinone derivatives DFT GIAO NMR |
| title | The Search for the Optimal Methodology for Predicting Fluorinated Cathinone Drugs NMR Chemical Shifts |
| title_full | The Search for the Optimal Methodology for Predicting Fluorinated Cathinone Drugs NMR Chemical Shifts |
| title_fullStr | The Search for the Optimal Methodology for Predicting Fluorinated Cathinone Drugs NMR Chemical Shifts |
| title_full_unstemmed | The Search for the Optimal Methodology for Predicting Fluorinated Cathinone Drugs NMR Chemical Shifts |
| title_short | The Search for the Optimal Methodology for Predicting Fluorinated Cathinone Drugs NMR Chemical Shifts |
| title_sort | search for the optimal methodology for predicting fluorinated cathinone drugs nmr chemical shifts |
| topic | cathinone fluorinated cathinone derivatives DFT GIAO NMR |
| url | https://www.mdpi.com/1420-3049/30/1/54 |
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