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- Publisher Website: 10.1021/jo0200825
- Scopus: eid_2-s2.0-0037189210
- PMID: 12076170
- WOS: WOS:000176472200039
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Article: Density functional theory investigation of the reaction of isodiiodomethane with acetylene: Potential utility of isodiiodomethane for cyclopropenation reactions
Title | Density functional theory investigation of the reaction of isodiiodomethane with acetylene: Potential utility of isodiiodomethane for cyclopropenation reactions |
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Authors | |
Keywords | Isomers Propylene Acetylene Carbenoid Chemical reaction |
Issue Date | 2002 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc |
Citation | Journal Of Organic Chemistry, 2002, v. 67 n. 13, p. 4619-4622 How to Cite? |
Abstract | We present density functional theory calculations for the reactions of CH2I - I and CH2I with acetylene (HC≡ CH) to form a cyclopropene product. CH2I - I readily reacts with HC≡CH to form a cyclopropene product and an I2 leaving group via a rate-determining step barrier of ∼3.9 kcal/mol (B3LYP/Sadlej-pVTZ). Calculations indicated that the CH2I radical reacts to form an iodopropenyl radical, which can close to a cyclopropene only with difficulty. Our results indicate that CH2I - I may act as an effective carbenoid to produce cyclopropenated products from alkynes. |
Persistent Identifier | http://hdl.handle.net/10722/167771 |
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 | Chen, DM | en_US |
dc.contributor.author | Li, YL | en_US |
dc.contributor.author | Phillips, DL | en_US |
dc.date.accessioned | 2012-10-08T03:11:22Z | - |
dc.date.available | 2012-10-08T03:11:22Z | - |
dc.date.issued | 2002 | en_US |
dc.identifier.citation | Journal Of Organic Chemistry, 2002, v. 67 n. 13, p. 4619-4622 | en_US |
dc.identifier.issn | 0022-3263 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/167771 | - |
dc.description.abstract | We present density functional theory calculations for the reactions of CH2I - I and CH2I with acetylene (HC≡ CH) to form a cyclopropene product. CH2I - I readily reacts with HC≡CH to form a cyclopropene product and an I2 leaving group via a rate-determining step barrier of ∼3.9 kcal/mol (B3LYP/Sadlej-pVTZ). Calculations indicated that the CH2I radical reacts to form an iodopropenyl radical, which can close to a cyclopropene only with difficulty. Our results indicate that CH2I - I may act as an effective carbenoid to produce cyclopropenated products from alkynes. | 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.subject | Isomers | - |
dc.subject | Propylene | - |
dc.subject | Acetylene | - |
dc.subject | Carbenoid | - |
dc.subject | Chemical reaction | - |
dc.title | Density functional theory investigation of the reaction of isodiiodomethane with acetylene: Potential utility of isodiiodomethane for cyclopropenation reactions | en_US |
dc.type | Article | en_US |
dc.identifier.email | Phillips, DL:phillips@hku.hk | en_US |
dc.identifier.authority | Phillips, DL=rp00770 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1021/jo0200825 | en_US |
dc.identifier.pmid | 12076170 | - |
dc.identifier.scopus | eid_2-s2.0-0037189210 | en_US |
dc.identifier.hkuros | 73898 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-0037189210&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 67 | en_US |
dc.identifier.issue | 13 | en_US |
dc.identifier.spage | 4619 | en_US |
dc.identifier.epage | 4622 | en_US |
dc.identifier.isi | WOS:000176472200039 | - |
dc.publisher.place | United States | en_US |
dc.identifier.scopusauthorid | Chen, DM=7405450267 | en_US |
dc.identifier.scopusauthorid | Li, YL=27168456500 | en_US |
dc.identifier.scopusauthorid | Phillips, DL=7404519365 | en_US |
dc.identifier.issnl | 0022-3263 | - |