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Calculation of the enthalpies of formation and proton affinities of some isoquinoline derivatives

Namazian, Mansoor; Coote, Michelle

Description

Ab initio molecular orbital theory has been used to calculate enthalpies of formation of isoquinoline, 1-hydroxyisoquinoline, 5-hydroxyisoquinoline, and 1,5-dihydroxyisoquinoline as well as some pyridine and quinoline derivatives. The proton affinities of the four isoquinoline derivatives were also obtained. The high-level composite methods G3(MP2), G3(MP2)//B3LYP, G3//B3LYP, and CBS-QB3 have been used for this study, and the results have been compared with available experimental values. For...[Show more]

dc.contributor.authorNamazian, Mansoor
dc.contributor.authorCoote, Michelle
dc.date.accessioned2015-12-10T22:28:18Z
dc.identifier.issn0021-9614
dc.identifier.urihttp://hdl.handle.net/1885/54418
dc.description.abstractAb initio molecular orbital theory has been used to calculate enthalpies of formation of isoquinoline, 1-hydroxyisoquinoline, 5-hydroxyisoquinoline, and 1,5-dihydroxyisoquinoline as well as some pyridine and quinoline derivatives. The proton affinities of the four isoquinoline derivatives were also obtained. The high-level composite methods G3(MP2), G3(MP2)//B3LYP, G3//B3LYP, and CBS-QB3 have been used for this study, and the results have been compared with available experimental values. For six of the eight studied compounds, the theoretical enthalpies of formation were very close to the experimental values (to within 4.3 kJ · mol-1); where comparison was possible, the theoretical and experimental proton affinities were also in excellent agreement with one another. However, there is an extraordinary discrepancy between theory and experiment for the enthalpies of formation of 1-hydroxyisoquinoline and 1,5-dihydroxyisoquinoline, suggesting that the experimental values for these two compounds should perhaps be re-examined. We also show that popular low cost computational methods such as B3LYP and MP2 show very large deviations from the benchmark values.
dc.publisherAcademic Press
dc.sourceJournal of Chemical Thermodynamics
dc.subjectKeywords: Computational methods; Experiments; Molecular orbitals; Protons; Ab initio molecular orbital theories; CBS-QB3; Composite methods; Enthalpies of formations; Enthalpy of formation; Experimental values; G3; Isoquinoline; Large deviations; Low costs; Proton Enthalpy of formation; G3; Isoquinoline; Proton affinity
dc.titleCalculation of the enthalpies of formation and proton affinities of some isoquinoline derivatives
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume40
dc.date.issued2008
local.identifier.absfor030799 - Theoretical and Computational Chemistry not elsewhere classified
local.identifier.absfor030399 - Macromolecular and Materials Chemistry not elsewhere classified
local.identifier.ariespublicationu4217927xPUB300
local.type.statusPublished Version
local.contributor.affiliationNamazian, Mansoor, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationCoote, Michelle, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue12
local.bibliographicCitation.startpage1627
local.bibliographicCitation.lastpage1631
local.identifier.doi10.1016/j.jct.2008.07.007
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2016-02-24T10:42:22Z
local.identifier.scopusID2-s2.0-56049084656
local.identifier.thomsonID000261847200002
CollectionsANU Research Publications

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