The transition state conformational effect on the activation energy of ethyl acetate neutral hydrolysis
We report a first-principles study on ethyl acetate neutral hydrolysis in which we focus on the activation energy variation resulting from the conformational effect in the transition state. We use the conformers of ethyl formate, ethyl acetate, ethyl fluoroacetate, and ethyl chloroacetate as the est...
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| Format: | Article |
| Language: | English |
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Elsevier
2019-09-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844019360694 |
| _version_ | 1828758299689877504 |
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| author | Febdian Rusydi Nufida D. Aisyah Rizka N. Fadilla Hermawan K. Dipojono Faozan Ahmad Mudasir Ira Puspitasari Andrivo Rusydi |
| author_facet | Febdian Rusydi Nufida D. Aisyah Rizka N. Fadilla Hermawan K. Dipojono Faozan Ahmad Mudasir Ira Puspitasari Andrivo Rusydi |
| author_sort | Febdian Rusydi |
| collection | DOAJ |
| description | We report a first-principles study on ethyl acetate neutral hydrolysis in which we focus on the activation energy variation resulting from the conformational effect in the transition state. We use the conformers of ethyl formate, ethyl acetate, ethyl fluoroacetate, and ethyl chloroacetate as the ester models and one water molecule with a one-step reaction mechanism. We also consider the long-range interaction and the surrounding water in the form of PCM. Our results show that the various conformers yield a significant range of activation energy. Moreover, the gauche conformer has lower activation energy than the trans conformer. The activation energy in its own right is lowered by the halogen atoms. Finally, we remark that the long-range correction and PCM stabilize the transition state geometry but raise the activation energy. |
| first_indexed | 2024-12-11T00:39:49Z |
| format | Article |
| id | doaj.art-d47ca580d1624401a1dabf74e156b533 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-12-11T00:39:49Z |
| publishDate | 2019-09-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-d47ca580d1624401a1dabf74e156b5332022-12-22T01:26:59ZengElsevierHeliyon2405-84402019-09-0159e02409The transition state conformational effect on the activation energy of ethyl acetate neutral hydrolysisFebdian Rusydi0Nufida D. Aisyah1Rizka N. Fadilla2Hermawan K. Dipojono3Faozan Ahmad4 Mudasir5Ira Puspitasari6Andrivo Rusydi7Department of Physics, Faculty of Science and Technology, Universitas Airlangga, Jl. Mulyorejo, Surabaya 60115, Indonesia; Research Center for Quantum Engineering Design, Faculty of Science and Technology, Universitas Airlangga, Jl. Mulyorejo, Surabaya 60115, Indonesia; Visiting Researcher at Precision Sciences & Technology and Applied Physics, Graduate School of Engineering, Osaka University, Suita 565-0871, Japan; Corresponding author at: Department of Physics, Faculty of Science and Technology, Universitas Airlangga, Jl. Mulyorejo, Surabaya 60115, Indonesia.Research Center for Quantum Engineering Design, Faculty of Science and Technology, Universitas Airlangga, Jl. Mulyorejo, Surabaya 60115, Indonesia; Department of Engineering Physics, Faculty of Industrial Engineering, Institut Teknologi Bandung, Bandung 40132, IndonesiaResearch Center for Quantum Engineering Design, Faculty of Science and Technology, Universitas Airlangga, Jl. Mulyorejo, Surabaya 60115, Indonesia; Department of Engineering Physics, Faculty of Industrial Engineering, Institut Teknologi Bandung, Bandung 40132, IndonesiaDepartment of Engineering Physics, Faculty of Industrial Engineering, Institut Teknologi Bandung, Bandung 40132, IndonesiaDepartment of Physics, Faculty of Mathematics and Science, Institut Pertanian Bogor, Bogor 16680, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Science, Universitas Gadjah Mada, Yogyakarta 55281, IndonesiaResearch Center for Quantum Engineering Design, Faculty of Science and Technology, Universitas Airlangga, Jl. Mulyorejo, Surabaya 60115, Indonesia; Information System Study Program, Faculty of Science and Technology, Universitas Airlangga, Jl. Mulyorejo, Surabaya 60115, IndonesiaDepartment of Physics, Faculty of Science, National University of Singapore, Singapore 117542, SingaporeWe report a first-principles study on ethyl acetate neutral hydrolysis in which we focus on the activation energy variation resulting from the conformational effect in the transition state. We use the conformers of ethyl formate, ethyl acetate, ethyl fluoroacetate, and ethyl chloroacetate as the ester models and one water molecule with a one-step reaction mechanism. We also consider the long-range interaction and the surrounding water in the form of PCM. Our results show that the various conformers yield a significant range of activation energy. Moreover, the gauche conformer has lower activation energy than the trans conformer. The activation energy in its own right is lowered by the halogen atoms. Finally, we remark that the long-range correction and PCM stabilize the transition state geometry but raise the activation energy.http://www.sciencedirect.com/science/article/pii/S2405844019360694Organic chemistryPhysical chemistryTheoretical chemistryLong-range correctionFirst-principles calculationsNeutral hydrolysis |
| spellingShingle | Febdian Rusydi Nufida D. Aisyah Rizka N. Fadilla Hermawan K. Dipojono Faozan Ahmad Mudasir Ira Puspitasari Andrivo Rusydi The transition state conformational effect on the activation energy of ethyl acetate neutral hydrolysis Heliyon Organic chemistry Physical chemistry Theoretical chemistry Long-range correction First-principles calculations Neutral hydrolysis |
| title | The transition state conformational effect on the activation energy of ethyl acetate neutral hydrolysis |
| title_full | The transition state conformational effect on the activation energy of ethyl acetate neutral hydrolysis |
| title_fullStr | The transition state conformational effect on the activation energy of ethyl acetate neutral hydrolysis |
| title_full_unstemmed | The transition state conformational effect on the activation energy of ethyl acetate neutral hydrolysis |
| title_short | The transition state conformational effect on the activation energy of ethyl acetate neutral hydrolysis |
| title_sort | transition state conformational effect on the activation energy of ethyl acetate neutral hydrolysis |
| topic | Organic chemistry Physical chemistry Theoretical chemistry Long-range correction First-principles calculations Neutral hydrolysis |
| url | http://www.sciencedirect.com/science/article/pii/S2405844019360694 |
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