Publicação
Computational studies on the reactivity of substituted 1,2-dihydro-1,2-azaborines
| dc.contributor.author | Silva, Pedro J. | |
| dc.contributor.author | Ramos, Maria João | |
| dc.date.accessioned | 2012-08-02T14:40:34Z | |
| dc.date.available | 2012-08-02T14:40:34Z | |
| dc.date.issued | 2009-07 | |
| dc.description.abstract | We have investigated important intermediates of electrophilic aromatic substitution reactions and one-electron oxidation of substituted 1,2-dihydro-1,2-azaborines with density-functional theory. The results show that electrophilic substitution reactions and one-electron oxidation of substituted 1,2-azaborines are generally much more favorable than those of the corresponding benzene derivatives. Both chlorination and nitration of several boron-unsubstituted 1,2-azaborines are expected to break the boron−hydrogen bond, yielding boron-chlorinated 1,2-azaborines and a novel class of boron-bound 1,2-azaborinyl nitrites, respectively. Comparison between the relative stabilities of C3-bound and C5-bound Wheland intermediates of different electrophilic substitution reactions of 1,2-azaborines further suggests that the preference of the C3- over C5-substitution decreases with decreasing electrophilicity of the attacking group. | por |
| dc.identifier.citation | Silva, Pedro J. e Ramos, Maria João (2009). Studies on the Reactivity of Substituted 1,2-Dihydro-1,2-azaborines. The Journal of Organic Chemistry, 74 (16), 6120-6129. DOI: 10.1021/jo900980d. ISSN 1520-6904. | por |
| dc.identifier.issn | 1520-6904 | |
| dc.identifier.uri | http://hdl.handle.net/10284/3293 | |
| dc.language.iso | eng | por |
| dc.peerreviewed | yes | por |
| dc.publisher | American Chemical Society | por |
| dc.relation.publisherversion | The definitive version is available at: http://pubs.acs.org/doi/abs/10.1021/jo900980d/ A versão definitiva está disponível em: http://pubs.acs.org/doi/abs/10.1021/jo900980d | por |
| dc.subject | 1,2-azaborines | por |
| dc.subject | Electrophilic aromatic substitution | por |
| dc.subject | Density-functional theory | por |
| dc.subject | Reactivity | por |
| dc.subject | FeClз | por |
| dc.title | Computational studies on the reactivity of substituted 1,2-dihydro-1,2-azaborines | por |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.citation.endPage | 6129 | |
| oaire.citation.issue | 16 | |
| oaire.citation.startPage | 6120 | |
| oaire.citation.title | Journal of Organic Chemistry | por |
| oaire.citation.volume | 74 | |
| person.familyName | Silva | |
| person.givenName | Pedro | |
| person.identifier.orcid | 0000-0001-9316-9275 | |
| person.identifier.scopus-author-id | 55310885700 | |
| rcaap.rights | openAccess | por |
| rcaap.type | article | por |
| relation.isAuthorOfPublication | f4a9230e-0a0e-45b6-b894-e71ded186ef2 | |
| relation.isAuthorOfPublication.latestForDiscovery | f4a9230e-0a0e-45b6-b894-e71ded186ef2 |
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