{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["8(49)"],"submitter":["Srirattanasakunsuk P"],"pubmed_abstract":["An efficient synthesis of 5,7-dihydroxy-4-methylcoumarin from phloroglucinol with ethyl acetoacetate in the UiO-66-SO<sub>3</sub>H metal-organic framework is reported. The potential of UiO-66-SO<sub>3</sub>H as a solid catalyst was determined through optimized-condition experiments and quantum molecular calculations. The optimal conditions for the synthesis of 5,7-dihydroxy-4-methylcoumarin with UiO-66-SO<sub>3</sub>H were as follows: phloroglucinol/ethyl acetoacetate molar ratio = 1:1.6, reaction time = 4 h, and temperature = 140 °C, for which the reaction yield reached 66.0%. The reusability of UiO-66-SO<sub>3</sub>H catalysts for Pechmann condensation was examined. The activation energy of the reaction occurring on a sulfonic group of the UiO-66-SO<sub>3</sub>H catalyst was 12.6 kcal/mol, which was significantly lower than 22.6 kcal/mol of the same reaction on the UiO-66 catalyst. To comprehend the reaction mechanism, density functional theory with the ONIOM approach was applied for the synthesis of coumarin on the UiO-66-SO<sub>3</sub>H and UiO-66 clusters. A possible reaction mechanism was proposed involving three steps: a trans-esterification step, an intramolecular hydroxyalkylation step, and a dehydration step. The rate-determining step was suggested to be the first step which acquired an activation energy of 15.7 and 29.5 kcal/mol, respectively. Information from this study can be used as guidelines to develop more efficient catalytic metal-organic frameworks for various organic syntheses."],"journal":["ACS omega"],"pagination":["46904-46913"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC10720004"],"repository":["biostudies-literature"],"pubmed_title":["Combined Experimental and Theoretical Study of the Synthesis of 5,7-Dihydroxy-4-methylcoumarin via a Pechmann Condensation in the Presence of UiO-66-SO<sub>3</sub>H Catalysts."],"pmcid":["PMC10720004"],"pubmed_authors":["Maihom T","Srirattanasakunsuk P","Jarussophon N","Treesukol P","Kongpatpanich K","Boekfa B","Limtrakul J"],"additional_accession":[]},"is_claimable":false,"name":"Combined Experimental and Theoretical Study of the Synthesis of 5,7-Dihydroxy-4-methylcoumarin via a Pechmann Condensation in the Presence of UiO-66-SO<sub>3</sub>H Catalysts.","description":"An efficient synthesis of 5,7-dihydroxy-4-methylcoumarin from phloroglucinol with ethyl acetoacetate in the UiO-66-SO<sub>3</sub>H metal-organic framework is reported. The potential of UiO-66-SO<sub>3</sub>H as a solid catalyst was determined through optimized-condition experiments and quantum molecular calculations. The optimal conditions for the synthesis of 5,7-dihydroxy-4-methylcoumarin with UiO-66-SO<sub>3</sub>H were as follows: phloroglucinol/ethyl acetoacetate molar ratio = 1:1.6, reaction time = 4 h, and temperature = 140 °C, for which the reaction yield reached 66.0%. The reusability of UiO-66-SO<sub>3</sub>H catalysts for Pechmann condensation was examined. The activation energy of the reaction occurring on a sulfonic group of the UiO-66-SO<sub>3</sub>H catalyst was 12.6 kcal/mol, which was significantly lower than 22.6 kcal/mol of the same reaction on the UiO-66 catalyst. To comprehend the reaction mechanism, density functional theory with the ONIOM approach was applied for the synthesis of coumarin on the UiO-66-SO<sub>3</sub>H and UiO-66 clusters. A possible reaction mechanism was proposed involving three steps: a trans-esterification step, an intramolecular hydroxyalkylation step, and a dehydration step. The rate-determining step was suggested to be the first step which acquired an activation energy of 15.7 and 29.5 kcal/mol, respectively. Information from this study can be used as guidelines to develop more efficient catalytic metal-organic frameworks for various organic syntheses.","dates":{"release":"2023-01-01T00:00:00Z","publication":"2023 Dec","modification":"2025-04-05T10:50:13.856Z","creation":"2025-04-05T10:50:13.856Z"},"accession":"S-EPMC10720004","cross_references":{"pubmed":["38107951"],"doi":["10.1021/acsomega.3c06624"]}}