A comparison of methods for measuring relative radical stabilities of carbon-centred radicals

dc.contributor.authorCoote, Michelle
dc.contributor.authorLin, Ching-Yeh
dc.contributor.authorBeckwith, Athelstan (Athel)
dc.contributor.authorZavistas, Andreas
dc.date.accessioned2015-12-10T22:56:26Z
dc.date.issued2010
dc.date.updated2016-02-24T10:44:04Z
dc.description.abstractThis article discusses and compares various methods for defining and measuring radical stability, including the familiar radical stabilization energy (RSE), along with some lesser-known alternatives based on corrected carbon-carbon bond energies, and more direct measures of the extent of radical delocalisation. As part of this work, a large set of R-H, R-CH3, R-Cl and R-R BDEs (R = CH2X, CH(CH3)X, C(CH3) 2X and X = H, BH2, CH3, NH2, OH, F, SiH3, PH2, SH, Cl, Br, N(CH3)2, NHCH3, NHCHO, NHCOCH3, NO2, OCF3, OCH2CH3, OCH3, OCHO, OCOCH3, Si(CH3)3, P(CH3)2, SC(CH 3)2CN, SCH2COOCH3, SCH 2COOCH3, SCH2Ph, SCH3, SO 2CH3, S(O)CH3, Ph, C6H 4-pCN, C6H4-pNO2, C 6H4-pOCH3, C6H4-pOH, CF2CF3, CF2H, CF3, CCl2H, CCl3, CH2Cl, CH2F, CH2OH, CH 2Ph, cyclo-CH(CH2)2, CH2CHCH 2, CH2CH3, CH(CH3)2, C(CH3)3, CCH, CHCH2, CHCHCH3, CHO, CN, COCH3, CON(CH2CH3)2, CONH 2, CONHCH3, COOC(CH3)3, COOCH 2CH3, COOCH3, COOH, COPh), and associated radical stability values are calculated using the high-level ab initio molecular orbital theory method G3(MP2)-RAD. These are used to compare the alternative radical stability schemes and illustrate principal structure-reactivity trends.
dc.identifier.issn1463-9076
dc.identifier.urihttp://hdl.handle.net/1885/60235
dc.publisherRoyal Society of Chemistry
dc.sourcePhysical Chemistry Chemical Physics
dc.subjectKeywords: carbon; free radical; article; chemistry; comparative study; thermodynamics; Carbon; Free Radicals; Thermodynamics
dc.titleA comparison of methods for measuring relative radical stabilities of carbon-centred radicals
dc.typeJournal article
local.bibliographicCitation.issue33
local.bibliographicCitation.lastpage9610
local.bibliographicCitation.startpage9597
local.contributor.affiliationCoote, Michelle, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationLin, Ching-Yeh, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBeckwith, Athelstan (Athel), College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationZavistas, Andreas, Long Island University
local.contributor.authoremailu4031074@anu.edu.au
local.contributor.authoruidCoote, Michelle, u4031074
local.contributor.authoruidLin, Ching-Yeh, u4169280
local.contributor.authoruidBeckwith, Athelstan (Athel), u810237
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030501 - Free Radical Chemistry
local.identifier.absfor030701 - Quantum Chemistry
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
local.identifier.ariespublicationu4217927xPUB529
local.identifier.citationvolume12
local.identifier.doi10.1039/c003880f
local.identifier.scopusID2-s2.0-77955890954
local.identifier.thomsonID000281007200004
local.identifier.uidSubmittedByu4217927
local.type.statusPublished Version

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