The theoretical study of electron-induced trimerization of acrylic acid anion radical in the gas phase.
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| Title: | The theoretical study of electron-induced trimerization of acrylic acid anion radical in the gas phase. |
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| Authors: | Tavakol, Hossein1 (AUTHOR) h_tavakol@iut.ac.ir, Shafieyoon, Parvaneh2 (AUTHOR) |
| Source: | Research on Chemical Intermediates. Aug2023, Vol. 49 Issue 8, p3645-3658. 14p. |
| Subjects: | Radical anions, Trimerization, Proton transfer reactions, Charge exchange, Ring formation (Chemistry), Dimerization |
| Abstract: | In this work, the electron-induced reaction of acrylic acid was studied using an FT-ICR-mass spectrometer and DFT calculations at M06-2X/aug-cc-pVTZ level of theory. The experiments showed the formation of acrylic acid trimer after 40 s as the major product. In the theoretical part, the structures and energies of various intermediates, transition states, and products were found via 4 different routes in five steps, consisting of electron transfer, proton transfer, dimerization, trimerization, and cyclization. The highest barriers belonged to the proton transfer step, which defined the kinetic of the process and the kinetic product. The reactions were only possible up to the formation of the acyclic trimer, and the cyclization process in the studied routes was kinetically and thermodynamically impossible. The calculated relative energies showed the possibility of two acyclic trimer structures as the major products. The first (I5-1) was the most stable and thermodynamic product with − 67.63 kcal/mol relative total electronic energy with a 12.38 kcal/mol overall barrier. The second (I5-2) was the kinetic product with a 10.55 kcal/mol barrier and − 55.21 kcal/mol relative total electronic energy versus the reactant. Because of the completion of the reaction in 40 s and at room temperature, the kinetic product was selected as the major product. [ABSTRACT FROM AUTHOR] |
| Copyright of Research on Chemical Intermediates is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
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| Header | DbId: egs DbLabel: Engineering Source An: 164875544 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: The theoretical study of electron-induced trimerization of acrylic acid anion radical in the gas phase. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Tavakol%2C+Hossein%22">Tavakol, Hossein</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> h_tavakol@iut.ac.ir</i><br /><searchLink fieldCode="AR" term="%22Shafieyoon%2C+Parvaneh%22">Shafieyoon, Parvaneh</searchLink><relatesTo>2</relatesTo> (AUTHOR) – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Research+on+Chemical+Intermediates%22">Research on Chemical Intermediates</searchLink>. Aug2023, Vol. 49 Issue 8, p3645-3658. 14p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Radical+anions%22">Radical anions</searchLink><br /><searchLink fieldCode="DE" term="%22Trimerization%22">Trimerization</searchLink><br /><searchLink fieldCode="DE" term="%22Proton+transfer+reactions%22">Proton transfer reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Charge+exchange%22">Charge exchange</searchLink><br /><searchLink fieldCode="DE" term="%22Ring+formation+%28Chemistry%29%22">Ring formation (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Dimerization%22">Dimerization</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: In this work, the electron-induced reaction of acrylic acid was studied using an FT-ICR-mass spectrometer and DFT calculations at M06-2X/aug-cc-pVTZ level of theory. The experiments showed the formation of acrylic acid trimer after 40 s as the major product. In the theoretical part, the structures and energies of various intermediates, transition states, and products were found via 4 different routes in five steps, consisting of electron transfer, proton transfer, dimerization, trimerization, and cyclization. The highest barriers belonged to the proton transfer step, which defined the kinetic of the process and the kinetic product. The reactions were only possible up to the formation of the acyclic trimer, and the cyclization process in the studied routes was kinetically and thermodynamically impossible. The calculated relative energies showed the possibility of two acyclic trimer structures as the major products. The first (I5-1) was the most stable and thermodynamic product with − 67.63 kcal/mol relative total electronic energy with a 12.38 kcal/mol overall barrier. The second (I5-2) was the kinetic product with a 10.55 kcal/mol barrier and − 55.21 kcal/mol relative total electronic energy versus the reactant. Because of the completion of the reaction in 40 s and at room temperature, the kinetic product was selected as the major product. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Research on Chemical Intermediates is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1007/s11164-023-05019-1 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 14 StartPage: 3645 Subjects: – SubjectFull: Radical anions Type: general – SubjectFull: Trimerization Type: general – SubjectFull: Proton transfer reactions Type: general – SubjectFull: Charge exchange Type: general – SubjectFull: Ring formation (Chemistry) Type: general – SubjectFull: Dimerization Type: general Titles: – TitleFull: The theoretical study of electron-induced trimerization of acrylic acid anion radical in the gas phase. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Tavakol, Hossein – PersonEntity: Name: NameFull: Shafieyoon, Parvaneh IsPartOfRelationships: – BibEntity: Dates: – D: 01 M: 08 Text: Aug2023 Type: published Y: 2023 Identifiers: – Type: issn-print Value: 09226168 Numbering: – Type: volume Value: 49 – Type: issue Value: 8 Titles: – TitleFull: Research on Chemical Intermediates Type: main |
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