DFT Study on the Reaction Mechanism of Cyclization of 2-Hydroxy Chalcone Catalyzed by Bronsted Acid with M06-2X Functional
Flavanones are one of the flavonoid group that has wide variety of applications such as a precursors in drug discovery. In the laboratory, flavanone is often synthesized from chalcone compounds. The conversion of chalcone to flavanone can be catalyzed by bronsted acid. The reaction mechanism for thi...
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| Format: | Article |
| Language: | English |
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Masyarakat Katalis Indonesia - Indonesian Catalyst Society (MKICS)
2021-12-01
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| Series: | Bulletin of Chemical Reaction Engineering & Catalysis |
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| Online Access: | https://journal.bcrec.id/index.php/bcrec/article/view/11487 |
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| author | Suci Zulaikha Hildayani Muhamad Abdulkadir Martoprawiro Yana Maolana Syah |
| author_facet | Suci Zulaikha Hildayani Muhamad Abdulkadir Martoprawiro Yana Maolana Syah |
| author_sort | Suci Zulaikha Hildayani |
| collection | DOAJ |
| description | Flavanones are one of the flavonoid group that has wide variety of applications such as a precursors in drug discovery. In the laboratory, flavanone is often synthesized from chalcone compounds. The conversion of chalcone to flavanone can be catalyzed by bronsted acid. The reaction mechanism for this process is proposed through the Michael addition reaction, however, the energetic details and the rate determining step for this reaction is not certainly known. This research aimed to investigate the reaction mechanism for chalcone-flavanone conversion with the present of bronsted acid as catalyst and also studied the effect of the solvent on the reaction energy profile with computational method. In this study, the modeling of the reaction mechanism for the said reaction was carried out using the DFT computational method with M06-2X functional. The computation was done both in the gas phase and in present of the solvent effect using the PCM models. The results showed that the mechanism of chalcone-flavanone conversion occurred in three steps which are protonation, cyclization, and then tautomerization. Based on these calculations, the rate determining step was the tautomerization reaction, which exhibited the same results with or without the solvent effects. Copyright © 2021 by Authors, Published by BCREC Group. This is an open access article under the CC BY-SA License (https://creativecommons.org/licenses/by-sa/4.0). |
| first_indexed | 2024-03-11T22:51:08Z |
| format | Article |
| id | doaj.art-d44177c1d80041e3917fbf8aefa56c22 |
| institution | Directory Open Access Journal |
| issn | 1978-2993 |
| language | English |
| last_indexed | 2024-03-11T22:51:08Z |
| publishDate | 2021-12-01 |
| publisher | Masyarakat Katalis Indonesia - Indonesian Catalyst Society (MKICS) |
| record_format | Article |
| series | Bulletin of Chemical Reaction Engineering & Catalysis |
| spelling | doaj.art-d44177c1d80041e3917fbf8aefa56c222023-09-22T03:36:14ZengMasyarakat Katalis Indonesia - Indonesian Catalyst Society (MKICS)Bulletin of Chemical Reaction Engineering & Catalysis1978-29932021-12-0116479680310.9767/bcrec.16.4.11487.796-8035460DFT Study on the Reaction Mechanism of Cyclization of 2-Hydroxy Chalcone Catalyzed by Bronsted Acid with M06-2X FunctionalSuci Zulaikha Hildayani0https://orcid.org/0000-0002-6164-1675Muhamad Abdulkadir Martoprawiro1Yana Maolana Syah2Physical Chemistry Group, Department of Chemistry, Institut Teknologi Bandung, Bandung 40116, IndonesiaPhysical Chemistry Group, Department of Chemistry, Institut Teknologi Bandung, Bandung 40116, IndonesiaOrganic Chemistry Group, Department of Chemistry, Institut Teknologi Bandung, Bandung 40116, IndonesiaFlavanones are one of the flavonoid group that has wide variety of applications such as a precursors in drug discovery. In the laboratory, flavanone is often synthesized from chalcone compounds. The conversion of chalcone to flavanone can be catalyzed by bronsted acid. The reaction mechanism for this process is proposed through the Michael addition reaction, however, the energetic details and the rate determining step for this reaction is not certainly known. This research aimed to investigate the reaction mechanism for chalcone-flavanone conversion with the present of bronsted acid as catalyst and also studied the effect of the solvent on the reaction energy profile with computational method. In this study, the modeling of the reaction mechanism for the said reaction was carried out using the DFT computational method with M06-2X functional. The computation was done both in the gas phase and in present of the solvent effect using the PCM models. The results showed that the mechanism of chalcone-flavanone conversion occurred in three steps which are protonation, cyclization, and then tautomerization. Based on these calculations, the rate determining step was the tautomerization reaction, which exhibited the same results with or without the solvent effects. Copyright © 2021 by Authors, Published by BCREC Group. This is an open access article under the CC BY-SA License (https://creativecommons.org/licenses/by-sa/4.0).https://journal.bcrec.id/index.php/bcrec/article/view/11487dftreaction mechanismchalcone conversionpcm modelsm06-2x |
| spellingShingle | Suci Zulaikha Hildayani Muhamad Abdulkadir Martoprawiro Yana Maolana Syah DFT Study on the Reaction Mechanism of Cyclization of 2-Hydroxy Chalcone Catalyzed by Bronsted Acid with M06-2X Functional Bulletin of Chemical Reaction Engineering & Catalysis dft reaction mechanism chalcone conversion pcm models m06-2x |
| title | DFT Study on the Reaction Mechanism of Cyclization of 2-Hydroxy Chalcone Catalyzed by Bronsted Acid with M06-2X Functional |
| title_full | DFT Study on the Reaction Mechanism of Cyclization of 2-Hydroxy Chalcone Catalyzed by Bronsted Acid with M06-2X Functional |
| title_fullStr | DFT Study on the Reaction Mechanism of Cyclization of 2-Hydroxy Chalcone Catalyzed by Bronsted Acid with M06-2X Functional |
| title_full_unstemmed | DFT Study on the Reaction Mechanism of Cyclization of 2-Hydroxy Chalcone Catalyzed by Bronsted Acid with M06-2X Functional |
| title_short | DFT Study on the Reaction Mechanism of Cyclization of 2-Hydroxy Chalcone Catalyzed by Bronsted Acid with M06-2X Functional |
| title_sort | dft study on the reaction mechanism of cyclization of 2 hydroxy chalcone catalyzed by bronsted acid with m06 2x functional |
| topic | dft reaction mechanism chalcone conversion pcm models m06-2x |
| url | https://journal.bcrec.id/index.php/bcrec/article/view/11487 |
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