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Exploration of Chromone-Based Thiosemicarbazone Derivatives: SC-XRD/DFT, Spectral (IR, UV-Vis) Characterization, and Quantum Chemical Analysis

Texto completo
Autor(es):
Basri, Rabia [1] ; Khalid, Muhammad [2] ; Shafiq, Zahid [1] ; Tahir, Muhammad Suleman [2] ; Khan, Muhammad Usman [3, 4] ; Tahir, Muhammad Nawaz [5] ; Naseer, Muhammad Moazzam [6] ; Carmo Braga, Ataualpa Albert [7]
Número total de Autores: 8
Afiliação do(s) autor(es):
[1] Bahauddin Zakariya Univ, Inst Chem Sci, Multan 60800 - Pakistan
[2] Khwaja Fareed Univ Engn & Informat Technol, Dept Chem, Rahim Yar Khan 64200 - Pakistan
[3] Govt Coll Univ, Dept Appl Chem, Faisalabad 38000 - Pakistan
[4] Univ Okara, Dept Chem, Okara 56300 - Pakistan
[5] Univ Sargodha, Dept Phys, Sargodha 40100 - Pakistan
[6] Quaid I Azam Univ, Dept Chem, Islamabad 45320 - Pakistan
[7] Univ Sao Paulo, Dept Quim Fundamental, Inst Quim, BR-05508000 Sao Paulo - Brazil
Número total de Afiliações: 7
Tipo de documento: Artigo Científico
Fonte: ACS OMEGA; v. 5, n. 46, p. 30176-30188, NOV 24 2020.
Citações Web of Science: 1
Resumo

By the condensation of thiosemicarbazide with coumarin aldehyde, two novel substituted thiosemicarbazones with chemical formulae C24H25N3O3S (3a) and C26H23N3O3S (3b) have been synthesized. The synthesized compounds were resolved using SC-XRD, and structure elucidation was carried out using H-1 NMR, C-13 NMR, UV-visible, and FT-IR spectroscopic analyses. Computational calculations at the B3LYP/6-311+G(d,p) level of theory were performed to countercheck the experimental (UV-vis, FT-IR) findings and explore the electronic (FMO, NBO, MEP) properties of 3a-b. The nonlinear optical (NLO) properties of 3a-b were estimated using B3LYP, HF, LC-BLYP, CAM-B3LYP, M062X, and M06 functionals in combination with the 6-311+G(d,p) basis set. The crystallographic data revealed that compounds were crystallized as an orthorhombic crystal lattice with the Pbcn space group and the triclinic crystal lattice with the P1 space group. A good concurrence among experimental SC-XRD-generated bond lengths, bond angles, FT-IR, UV-vis, and corresponding DFT results was found, which confirms the purity of both compounds. The NBO analysis confirmed the presence of intramolecular hydrogen bonding and hyperconjugative interactions, which not only were the pivotal cause of stability of the investigated compounds but also led to an overwhelming NLO response. The energy differences calculated for HOMO/LUMO are 3.053 and 3.118 eV in 3a and 3b, respectively. The crystal 3b showed a higher value of first-order polarizability at all levels of theory than 3a. Overall results show that the crystals under investigation are polarized in nature with a good dipole moment. A comparative analysis with urea molecules clearly indicates that the studied compounds are acceptable NLO candidates and they can be used for future technological applications. (AU)

Processo FAPESP: 11/07895-8 - Estudo teórico das reações de Heck-Matsuda
Beneficiário:Ataualpa Albert Carmo Braga
Linha de fomento: Bolsas no Brasil - Pós-Doutorado
Processo FAPESP: 14/25770-6 - Novas fronteiras em reações de acoplamento cruzado mediadas por paládio: associando catálise enantiosseletiva, ativações C-H, novos materiais e reações em fluxo visando alta eficiência e sustentabilidade em processos sintéticos
Beneficiário:Carlos Roque Duarte Correia
Linha de fomento: Auxílio à Pesquisa - Temático
Processo FAPESP: 15/01491-3 - Estudo teórico das reações de acoplamento-cruzado: catálise homogênea e heterogênea
Beneficiário:Ataualpa Albert Carmo Braga
Linha de fomento: Auxílio à Pesquisa - Regular