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Structural investigation of nitrogen-linked saccharinate–tetrazole

2011Journal article Restricted access
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dc.contributor.authorGómez-Zavaglia, A.
dc.contributor.authorIsmael, Amin
dc.contributor.authorCabral, Lília
dc.contributor.authorKaczor, A.
dc.contributor.authorPaixão, J. A.
dc.contributor.authorFausto, R.
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.date.accessioned2014-06-07T11:34:53Z
dc.date.available2014-06-07T11:34:53Z
dc.date.issued2011
dc.date.updated2014-06-05T09:09:57Z
dc.description.abstractThe molecular structure of nitrogen-linked saccharinate–tetrazole, N-(1,1-dioxo-1,2-benzisothiazol-3-yl)-amine-1H-tetrazole (BAT), was investigated in the crystalline state using X-ray crystallography and infrared and Raman spectroscopies, and isolated in argon matrix by infrared spectroscopy. Interpretation of the experimental results was supported by quantum chemical calculations undertaken at the DFT(B3LYP)/6-311++G(3df,3pd) level of theory. In the neat crystalline solid (space group C2/c, a = 21.7493(3) Å, b = 8.85940(10) Å, c = 10.76900(10) Å, b = 103.3300(10) deg; Z = 8), BAT units exist in the (1H)-tetrazole aminosaccharin tautomeric form, with the NH spacer establishing a hydrogen bond to the nitrogen in position-4 of the tetrazole group of a neighbour molecule, and the NH group of the tetrazole fragment forming a bifurcated H-bond to the saccharyl nitrogen of the same molecule and to one of the oxygen atoms of a second neighbour molecule. On the other hand, according to both the matrix isolation infrared studies and the theoretical calculations, the isolated BAT molecule exists preferentially as the (1H)-tetrazole iminosaccharin tautomer, where the main stabilizing interaction is the intramolecular H-bond established between the NH group of the saccharyl ring and the tetrazole nitrogen atom in position 4. A detailed conformational analysis of the studied molecule and full assignment of the vibrational spectra for both the matrix-isolated compound and crystalline sample were undertaken.por
dc.identifier.citationGómez-Zavaglia, A.; Ismael, A.; Cabral, L.I.L.; Kaczor, A.; Paixão, J.A.; Fausto, R.; Cristiano, M.L.S. Structural investigation of nitrogen-linked saccharinate–tetrazole, Journal of Molecular Structure, 1003, 1-3, 103-110, 2011.por
dc.identifier.doihttp://dx.doi.org/10.1016/j.molstruc.2011.07.044
dc.identifier.issn0022-2860
dc.identifier.otherAUT: MCR00716;
dc.identifier.urihttp://hdl.handle.net/10400.1/4245
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherElsevierpor
dc.subjectSaccharinate-tetrazolepor
dc.subjectConformational analysispor
dc.subjectX-ray crystallographypor
dc.subjectDFT calculationspor
dc.subjectMatrix-isolation infrared spectroscopypor
dc.subjectSolid state infrared and Ramanpor
dc.subjectSpectroscopiespor
dc.titleStructural investigation of nitrogen-linked saccharinate–tetrazolepor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage110por
oaire.citation.issue1-3por
oaire.citation.startPage103por
oaire.citation.titleJournal of Molecular Structurepor
oaire.citation.volume1003por
person.familyNameIsmael
person.familyNameCabral
person.familyNameCristiano
person.givenNameAmin
person.givenNameLília
person.givenNameMaria de Lurdes
person.identifier.ciencia-id3510-24A8-36B6
person.identifier.ciencia-idE411-6006-5A01
person.identifier.orcid0000-0002-7346-5998
person.identifier.orcid0000-0001-9362-8128
person.identifier.orcid0000-0002-9447-2855
person.identifier.ridA-8153-2013
person.identifier.ridM-4279-2013
person.identifier.ridG-2345-2012
person.identifier.scopus-author-id35203489500
person.identifier.scopus-author-id9238724800
rcaap.rightsrestrictedAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublicationfa01ef7f-7a2a-4f74-a405-714360b862f3
relation.isAuthorOfPublication175a6aa3-9993-480b-9663-ed083a17eedf
relation.isAuthorOfPublicationb16751a6-748e-44b0-9c59-058cbd5b2cc3
relation.isAuthorOfPublication.latestForDiscovery175a6aa3-9993-480b-9663-ed083a17eedf

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