DFT Studies on the Stereoselective Three-Component Ugi Reaction
studied theoretically based on DFT calculations. Structures of reagents, products, intermediates, and transition states were optimized at M062X/6-31+g(d,p) level of theory in gas phase and in methanol as a common solvent for this reaction. The reaction takes place through several processes, includin...
| Authors: | ; |
|---|---|
| Format: | Article |
| Status: | Published version |
| Publication date: | 2019 |
| Country: | Brasil |
| Institution: | UFMS |
| Repository: | Orbital - The Electronic Journal of Chemistry (Campo Grande) |
| Language: | English |
| OAI Identifier: | oai:periodicos.ufms.br:article/16004 |
| Online Access: | https://periodicos.ufms.br/index.php/orbital/article/view/16004 |
| Access Level: | Open access |
| Keyword: | DFT calculation multicomponent reaction stereoselectivity three-component Ugi reaction |
| _version_ | 1878757149338763264 |
|---|---|
| author | Sharifzadeh, Elaheh Sadat |
| author2 | Shiraz, Nader Zabarjad |
| author2_role | author |
| author_browse | Sharifzadeh, Elaheh Sadat Shiraz, Nader Zabarjad |
| author_facet | Sharifzadeh, Elaheh Sadat Shiraz, Nader Zabarjad |
| author_role | author |
| collection | Orbital - The Electronic Journal of Chemistry (Campo Grande) |
| description | studied theoretically based on DFT calculations. Structures of reagents, products, intermediates, and transition states were optimized at M062X/6-31+g(d,p) level of theory in gas phase and in methanol as a common solvent for this reaction. The reaction takes place through several processes, including atom inversion, bond rotation, acid-base, nucleophile-electrophile competitions. These diverse phenomena were studied to provide a clearer picture of the mechanism of this valuable reaction, especially in terms of stereochemistry considerations. According to the results, the enthalpy of the reaction was -45.9 and -41.2 kcal/mol for the dominant product in gas phase and in methanol. The stereoselectivity of the reaction was under the kinetic control of nucleophilic attack of isocyanide to less hindered si-face (Ea= 4.1 compared to 7.4 kcal/mol for re-face) of more stable chiral (E)-iminium in methanol. DOI: http://dx.doi.org/10.17807/orbital.v11i1.1214 |
| eu_rights_str_mv | openAccess |
| format | article |
| id | BR_6adc6e0d26ec00a354b7fedf54d5246d |
| institution | UFMS |
| instname_str | Universidade Federal de Mato Grosso do Sul (UFMS) |
| language | eng |
| network_acronym_str | BR |
| network_name_str | Brasil |
| oai_identifier_str | oai:periodicos.ufms.br:article/16004 |
| publishDate | 2019 |
| publishDateSort | 2019 |
| publisher | Instituto de Química, Universidade Federal de Mato Grosso do Sul |
| publisherStr | Instituto de Química, Universidade Federal de Mato Grosso do Sul |
| reponame_str | Orbital - The Electronic Journal of Chemistry (Campo Grande) |
| spelling | DFT Studies on the Stereoselective Three-Component Ugi Reaction Sharifzadeh, Elaheh Sadat Shiraz, Nader Zabarjad DFT calculation multicomponent reaction stereoselectivity three-component Ugi reaction studied theoretically based on DFT calculations. Structures of reagents, products, intermediates, and transition states were optimized at M062X/6-31+g(d,p) level of theory in gas phase and in methanol as a common solvent for this reaction. The reaction takes place through several processes, including atom inversion, bond rotation, acid-base, nucleophile-electrophile competitions. These diverse phenomena were studied to provide a clearer picture of the mechanism of this valuable reaction, especially in terms of stereochemistry considerations. According to the results, the enthalpy of the reaction was -45.9 and -41.2 kcal/mol for the dominant product in gas phase and in methanol. The stereoselectivity of the reaction was under the kinetic control of nucleophilic attack of isocyanide to less hindered si-face (Ea= 4.1 compared to 7.4 kcal/mol for re-face) of more stable chiral (E)-iminium in methanol. DOI: http://dx.doi.org/10.17807/orbital.v11i1.1214 Instituto de Química, Universidade Federal de Mato Grosso do Sul https://periodicos.ufms.br/index.php/orbital/article/view/16004 |
| spellingShingle | DFT Studies on the Stereoselective Three-Component Ugi Reaction Sharifzadeh, Elaheh Sadat DFT calculation multicomponent reaction stereoselectivity three-component Ugi reaction |
| status_str | publishedVersion |
| title | DFT Studies on the Stereoselective Three-Component Ugi Reaction |
| title_full | DFT Studies on the Stereoselective Three-Component Ugi Reaction |
| title_fullStr | DFT Studies on the Stereoselective Three-Component Ugi Reaction |
| title_full_unstemmed | DFT Studies on the Stereoselective Three-Component Ugi Reaction |
| title_short | DFT Studies on the Stereoselective Three-Component Ugi Reaction |
| title_sort | DFT Studies on the Stereoselective Three-Component Ugi Reaction |
| topic | DFT calculation multicomponent reaction stereoselectivity three-component Ugi reaction |
| topic_facet | DFT calculation multicomponent reaction stereoselectivity three-component Ugi reaction |
| url | https://periodicos.ufms.br/index.php/orbital/article/view/16004 |