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Investigation on the aromaticity of 1,3,4-thiadiazole-2-thione and its oxygen analogs including their tautomeric forms

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dc.contributor.authorERDEM, SAFİYE
dc.contributor.authorsErdem, SS; Ozpinar, GA; Sacan, MT
dc.date.accessioned2022-03-12T17:19:57Z
dc.date.available2022-03-12T17:19:57Z
dc.date.issued2005
dc.description.abstractThe aromaticity of 1,3,4-thiadiazole-2-thione and its oxygen analogs including their tautomeric forms, and 1,3,4-thiadiazole, 1,3,4-oxadiazole, furan, thiophene, cyclopentadiene, the cyclopentadienyl anion and the cyclopentadienyl cation has been examined by harmonic oscillator measure of aromaticity (HOMA), aromatic stabilization energy (ASE), differential heat of hydrogenation (Delta Delta HH), and nucleus independent chemical shifts (NICS (0)), calculated at the HF/6-31G**, B3LYP/6-31G**, B3LYP/6-311G**, and B3LYP/6-311 + +G** levels. A principal component analysis (PCA) of the data set generated from these aromaticity results has been presented and compared with similar analyses in the recent literature. It has been shown that aromaticity is at least a two-dimensional phenomenon, independent of the level of the computational method employed. We observed that the sulfur-containing heterocyclic compounds are more aromatic than their oxygen analogs according to geometrical aromaticity measurements. In addition, our calculations of the energies of the tautomeric forms showed that the carbonyl and thiocarbonyl tautomers are more stable than the hydroxy and mercapto forms, which is in good agreement with the experimental findings in the literature. (c) 2005 Elsevier B.V. All rights reserved.
dc.identifier.doi10.1016/j.theochem.2005.04.019
dc.identifier.issn0166-1280
dc.identifier.urihttps://hdl.handle.net/11424/228175
dc.identifier.wosWOS:000231275600029
dc.language.isoeng
dc.publisherELSEVIER SCIENCE BV
dc.relation.ispartofJOURNAL OF MOLECULAR STRUCTURE-THEOCHEM
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjecthetero-aromatic tautomerism
dc.subjectharmonic oscillator measure of aromaticity
dc.subjectaromatic stabilization energy
dc.subjectnucleus independent chemical shifts
dc.subjectprincipal component analysis
dc.subjectPI-ELECTRON SYSTEMS
dc.subject5-MEMBERED HETEROCYCLES
dc.subjectMOLECULAR-STRUCTURE
dc.subjectRESONANCE ENERGY
dc.subjectDFT CALCULATIONS
dc.subjectDERIVATIVES
dc.subject2-ARYL-DELTA(2)-1,3,4-OXADIAZOLINE-5-THIONES
dc.subject1,3,4-OXADIAZOLE-2-THIONE
dc.subject1,1-DIOXIDE
dc.subjectMODEL
dc.titleInvestigation on the aromaticity of 1,3,4-thiadiazole-2-thione and its oxygen analogs including their tautomeric forms
dc.typearticle
dspace.entity.typePublication
local.avesis.id7a83c3e7-34db-4c06-8e7b-7a189858b095
local.import.packageSS17
local.indexed.atWOS
local.indexed.atSCOPUS
local.journal.numberofpages11
oaire.citation.endPage243
oaire.citation.issue1-3
oaire.citation.startPage233
oaire.citation.titleJOURNAL OF MOLECULAR STRUCTURE-THEOCHEM
oaire.citation.volume726
relation.isAuthorOfPublication99f2f09c-7e48-402f-9bb9-ccdd73c27ec2
relation.isAuthorOfPublication.latestForDiscovery99f2f09c-7e48-402f-9bb9-ccdd73c27ec2

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