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- Publisher Website: 10.1021/jo052328m
- Scopus: eid_2-s2.0-33644641632
- PMID: 16496984
- WOS: WOS:000235896800027
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Article: A density functional theory study of the 5-exo cyclization reactions of α-substituted 6,6-diphenyl-5-hexenyl radicals
Title | A density functional theory study of the 5-exo cyclization reactions of α-substituted 6,6-diphenyl-5-hexenyl radicals |
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Authors | |
Issue Date | 2006 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc |
Citation | Journal Of Organic Chemistry, 2006, v. 71 n. 5, p. 1984-1988 How to Cite? |
Abstract | Density functional theory computations were done to study the 5-exo radical cyclization reactions of α-substituted 6,6-diphenyl-5-hexenyl radicals. The methoxy electron donor group substitution reduced the barrier to reaction by about 0.5 kcal/mol. On the other hand, the electron acceptor group substitutions (ethoxycarbonyl, carboxylic acid, carboxylate, and cyano) raised the barrier to reaction by varying amounts (0.5-2.1 kcal /mol). The entropic terms of these cyclization reactions are briefly discussed. Solvent effects on these reactions were explored by calculations that included a polarizable continuum model for the solvent. The density functional theory calculated results were found to be in good agreement with the experimental data available in the literature and help to explain some of the observed variation in these types of cyclization reactions with various substitutions. Our results also provide an explanation for why the rate constant for the carboxylate group substituted radical was found to be an order of magnitude smaller than the rate constant for those radicals with carboxylic acid and ethoxycarbonyl substitutions. © 2006 American Chemical Society. |
Persistent Identifier | http://hdl.handle.net/10722/168007 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
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dc.contributor.author | Guan, X | en_US |
dc.contributor.author | Phillips, DL | en_US |
dc.contributor.author | Yang, D | en_US |
dc.date.accessioned | 2012-10-08T03:14:01Z | - |
dc.date.available | 2012-10-08T03:14:01Z | - |
dc.date.issued | 2006 | en_US |
dc.identifier.citation | Journal Of Organic Chemistry, 2006, v. 71 n. 5, p. 1984-1988 | en_US |
dc.identifier.issn | 0022-3263 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/168007 | - |
dc.description.abstract | Density functional theory computations were done to study the 5-exo radical cyclization reactions of α-substituted 6,6-diphenyl-5-hexenyl radicals. The methoxy electron donor group substitution reduced the barrier to reaction by about 0.5 kcal/mol. On the other hand, the electron acceptor group substitutions (ethoxycarbonyl, carboxylic acid, carboxylate, and cyano) raised the barrier to reaction by varying amounts (0.5-2.1 kcal /mol). The entropic terms of these cyclization reactions are briefly discussed. Solvent effects on these reactions were explored by calculations that included a polarizable continuum model for the solvent. The density functional theory calculated results were found to be in good agreement with the experimental data available in the literature and help to explain some of the observed variation in these types of cyclization reactions with various substitutions. Our results also provide an explanation for why the rate constant for the carboxylate group substituted radical was found to be an order of magnitude smaller than the rate constant for those radicals with carboxylic acid and ethoxycarbonyl substitutions. © 2006 American Chemical Society. | en_US |
dc.language | eng | en_US |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc | en_US |
dc.relation.ispartof | Journal of Organic Chemistry | en_US |
dc.title | A density functional theory study of the 5-exo cyclization reactions of α-substituted 6,6-diphenyl-5-hexenyl radicals | en_US |
dc.type | Article | en_US |
dc.identifier.email | Phillips, DL:phillips@hku.hk | en_US |
dc.identifier.email | Yang, D:yangdan@hku.hk | en_US |
dc.identifier.authority | Phillips, DL=rp00770 | en_US |
dc.identifier.authority | Yang, D=rp00825 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1021/jo052328m | en_US |
dc.identifier.pmid | 16496984 | - |
dc.identifier.scopus | eid_2-s2.0-33644641632 | en_US |
dc.identifier.hkuros | 119094 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-33644641632&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 71 | en_US |
dc.identifier.issue | 5 | en_US |
dc.identifier.spage | 1984 | en_US |
dc.identifier.epage | 1988 | en_US |
dc.identifier.isi | WOS:000235896800027 | - |
dc.publisher.place | United States | en_US |
dc.identifier.scopusauthorid | Guan, X=8313149700 | en_US |
dc.identifier.scopusauthorid | Phillips, DL=7404519365 | en_US |
dc.identifier.scopusauthorid | Yang, D=7404800756 | en_US |
dc.identifier.issnl | 0022-3263 | - |