Molecular and supramolecular properties of nitroaromatic thiosemicarbazones: synthesis, spectroscopy, X-ray structure elucidation and DFT calculations

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dc.creatorLuiz Carlos Dias
dc.creatorGeraldo Magela de Lima
dc.creatorCarlos Basílio Pinheiro
dc.creatorMarco Antonio Chaer do Nascimento
dc.creatorRodrigo da Silva Bitzer
dc.date.accessioned2023-07-24T13:14:34Z
dc.date.accessioned2025-09-09T00:52:25Z
dc.date.available2023-07-24T13:14:34Z
dc.date.issued2017
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipFAPERJ - Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro
dc.identifier.doihttps://doi.org/10.1016/j.molstruc.2016.11.039
dc.identifier.issn1872-8014
dc.identifier.urihttps://hdl.handle.net/1843/56874
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of Molecular Structure
dc.rightsAcesso Restrito
dc.subjectTeoria do funcional da densidade
dc.subject.otherNitroaromatic compounds
dc.subject.otherThiosemicarbazones
dc.subject.otherX-ray structure analysis
dc.subject.otherHirshfeld surface analysis
dc.subject.otherDFT calculations
dc.titleMolecular and supramolecular properties of nitroaromatic thiosemicarbazones: synthesis, spectroscopy, X-ray structure elucidation and DFT calculations
dc.typeArtigo de periódico
local.citation.epage86
local.citation.spage79
local.citation.volume1131
local.description.resumoThe reactions of 6-nitropiperonal with H2Nsingle bondNHsingle bondC(S)single bondNHR, R = Me, Et, Ph or H, afforded four nitroaromatic thiosemicarbazones 1–4, respectively. 1–4 were characterized by elemental analysis (CHN), FTIR, and 1H and 13C{1H} NMR spectroscopy. In addition, the crystal structures of 2 and 3 were determined by single-crystal X-ray diffraction. Our X-ray structural results have shown that the nitropiperonal and thiosemicarbazone moieties exhibit an almost coplanar arrangement for both 2 and 3. Moreover, they establish 2-D networks along the [111] base vector by means of classical and nonclassical hydrogen bonds. Electronic and spectroscopic properties of 1–4 were investigated at the DFT B3LYP/6-311G** level of calculation. The Cdouble bondS group of 1–4 constitutes a nucleophilic region, whereas the NO2 group defines an electrophilic centre, as expected. Furthermore, a DFT vibrational analysis of 4 allowed a reliable assignment of the thiosemicarbazone-based vibrations. Also, a good agreement between theoretical and experimental 13C chemical shift values was obtained for 1–4.
local.identifier.orcidhttps://orcid.org/0000-0002-3816-0320
local.identifier.orcidhttps://orcid.org/0000-0002-8674-1779
local.identifier.orcidhttps://orcid.org/0000-0002-6940-3110
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE FÍSICA
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.sciencedirect.com/science/article/pii/S0022286016312005?via%3Dihub

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