O-4-Acetylamino-benzenesulfonylated pyrimidine derivatives: synthesis, SC-XRD, DFT analysis and electronic behaviour investigation

Autor(es)

Khalid, Muhammad ^[1] ; Ali, Akbar ^{[2, 3]} ; Haq, Sadia ^[1] ; Tahir, Muhammad Nawaz ^[4] ; Iqbal, Javed ^[5] ; Braga, Ataualpa A. C. ^[6] ; Ashfaq, Muhammad ^[4] ; Akhtar, Samee Ul Hassan ^[4]

Afiliação do(s) autor(es)

^[1] Khwaja Fareed Univ Engn & Informat Technol, Dept Chem & Humanities, Rahim Yar Khan 64200 - Pakistan

^[2] Univ Sargodha, Dept Chem, Sargodha 40100 - Pakistan

^[3] Univ Malakand, Dept Chem, Lower Dir 18800, Khyber Pakhtunk - Pakistan

^[4] Univ Sargodha, Dept Phys, Sargodha - Pakistan

^[5] Univ Agr Faisalabad, Dept Chem, Faisalabad 38000 - Pakistan

^[6] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Av Prof Lineu Prestes 748, BR-05508000 Sao Paulo - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Molecular Structure; v. 1224, JAN 15 2021.
• Citações Web of Science: 0

Resumo

Beginning with 2-amino-6-methyl-pyrimidin-4-ol and 2,6-diamino-pyrimidin-4-ol, 2-amino-6-methylpyrimidin-4-yl 4-acetamidobenzenesulfonate (APABS) and 2,6-diaminopyrimidin-4-yl 4-acetamidobenzenesulfonate (DPACS) were synthesized respectively through O-4-acetylaminobenzenesulfonylation reaction. The structures of the (APABS) and (DPACS) were verified unambiguously by the single crystal X-ray diffraction technique. The X-ray diffraction inspection inferred that these chemical architectures are stabilized by intermolecular attractive forces. The quantum chemical examination of optimized geometry, vibraional analysis and natural bond orbitals (NBOs) properties for APABS and DPACS were attained by adopting B3LYP/6-311G(d,p) level. Moreover, the frontier molecular orbitals (FMOs) analysis was determined by TD-DFT/B3LYP/6-311G(d,p) level. The simulated structural parameters and XRD results of APABS and DPACS were found in close agreement to that of concerned experimental findings. The molecular stability owing to strongest hyperconjugative interactions in APABS and DPACS was evaluated through NBO investigation. The transfer of charge phenonmenon in the entitled compounds was evaluated by FMOs. The increasing order of energy gap for compounds is APABS<DPACS. Frontier molecular orbital energies of entitled compounds are also used to calculate the global reativity indices. The engagement of various sites in terms of chemical reactivities were determined by molecular eletrosatic potential analysis. Moreover, hirshfeldsurfaces were studied which supported the X-ray diffraction investigation in terms of intermolecular attractive forces. (C) 2020 Elsevier B.V. All rights reserved. (AU)

• 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