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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
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?
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
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

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

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