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Article: Density functional theory investigation of the reaction of isodiiodomethane with acetylene: Potential utility of isodiiodomethane for cyclopropenation reactions

TitleDensity functional theory investigation of the reaction of isodiiodomethane with acetylene: Potential utility of isodiiodomethane for cyclopropenation reactions
Authors
Chen, DMLi, YLPhillips, DL
KeywordsIsomers
Propylene
Acetylene
Carbenoid
Chemical reaction
Issue Date2002
PublisherAmerican 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?
DOI: http://dx.doi.org/10.1021/jo0200825
AbstractWe 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 Identifierhttp://hdl.handle.net/10722/167771
ISSN
0022-3263
2023 Impact Factor: 3.3
2023 SCImago Journal Rankings: 0.724
ISI Accession Number ID
WOS:000176472200039
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorChen, DMen_US
dc.contributor.authorLi, YLen_US
dc.contributor.authorPhillips, DLen_US
dc.date.accessioned2012-10-08T03:11:22Z-
dc.date.available2012-10-08T03:11:22Z-
dc.date.issued2002en_US
dc.identifier.citationJournal Of Organic Chemistry, 2002, v. 67 n. 13, p. 4619-4622en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/10722/167771-
dc.description.abstractWe 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.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_US
dc.relation.ispartofJournal of Organic Chemistryen_US
dc.subjectIsomers-
dc.subjectPropylene-
dc.subjectAcetylene-
dc.subjectCarbenoid-
dc.subjectChemical reaction-
dc.titleDensity functional theory investigation of the reaction of isodiiodomethane with acetylene: Potential utility of isodiiodomethane for cyclopropenation reactionsen_US
dc.typeArticleen_US
dc.identifier.emailPhillips, DL:phillips@hku.hken_US
dc.identifier.authorityPhillips, DL=rp00770en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/jo0200825en_US
dc.identifier.pmid12076170-
dc.identifier.scopuseid_2-s2.0-0037189210en_US
dc.identifier.hkuros73898-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0037189210&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume67en_US
dc.identifier.issue13en_US
dc.identifier.spage4619en_US
dc.identifier.epage4622en_US
dc.identifier.isiWOS:000176472200039-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridChen, DM=7405450267en_US
dc.identifier.scopusauthoridLi, YL=27168456500en_US
dc.identifier.scopusauthoridPhillips, DL=7404519365en_US
dc.identifier.issnl0022-3263-

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