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

• Published in: Journal of molecular structure 2021-01, Vol.1224, p.129308, Article 129308
• Main Authors: Khalid, Muhammad, Ali, Akbar, Haq, Sadia, Tahir, Muhammad Nawaz, Iqbal, Javed, Braga, Ataualpa A.C., Ashfaq, Muhammad, Akhtar, Samee Ul Hassan
• Format: Article
• Language: English
• Subjects: Benzenesulfonylation; DFT analysis; Pyrimidine; X-ray diffraction
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2020.129308

•Facile synthesis of O-4-Acetylamino-benzenesulfonylated pyrimidines have achieved.•The structures were verified by the X-ray crystallographic technique.•Detailed DFT was performed for the exploration of NLO, FMOs, and NBOs.•Hirshfeld surfaces analysis confirmed the presence of intermolecular interactions.•The calculated findings display a good agreement with experimental data. 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-acetylamino-benzenesulfonylation 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. [Display omitted]