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Synthesis and structural characterization and DFT calculations of the organic salt crystal obtaining 9-aminoacridine and picric acid: 9-Aminoacridinium picrate
Fatma Aydin (1,*) , Nahide Burcu Arslan (2)
(1) Department of Chemistry, Sciences Faculty, Çanakkale Onsekiz Mart University, 17100, Çanakkale, Turkey
(2) Department of Computer Education and Instructional Technology, Faculty of Education, Giresun University, 28200, Giresun, Turkey
(*) Corresponding Author
Received: 15 Jun 2023 | Revised: 17 Jul 2023 | Accepted: 26 Jul 2023 | Published: 30 Sep 2023 | Issue Date: September 2023
Organic salt, 9-aminoacridinium picrate (9-AAcPc), containing equimolar quantities of 9-aminoacridine and picric acid was obtained and a single crystal was grown by the slow evaporation method in the mixture of methanol: tetrahydrofuran solvent (1: 1, v: v). The molecular structure of the prepared compound was confirmed by FT-IR, 1H NMR, and 13C NMR spectroscopic methods, as well as single crystal X-ray diffraction analysis. The X-ray diffraction analysis of the crystal structure of the title compound showed the presence of the triclinic space group P-1 with no. 2, a = 8.2811(7) Å, b = 10.1003(9) Å, c = 13.4484(13) Å, α = 83.521(3)°, β = 83.330(3)°, γ = 66.595(3)°, V = 1022.56(16) Å3, Z = 2, μ(MoKα) = 0.108 mm-1, Dcalc = 1.375 g/cm3, 56338 reflections measured (5.89° ≤ 2Θ ≤ 56.704°), 5097 unique (Rint = 0.0400, Rsigma = 0.0210) which were used in all calculations. The final R1 was 0.0552 (I > 2σ(I)) and wR2 was 0.1757 (all data). The molecular geometry was also optimized using density functional theory. The frontier molecular orbitals were calculated, and we discussed the probability that the proton transfers from the phenolic OH group of picric acid to different nitrogen units. The calculated electronic structure properties of the title molecule, such as the HOMO and LUMO analysis, and different molecular electrostatic potential maps, were obtained by using the density functional theory method, and the calculated structure was compared with the experimental structure. The thermal stability of the crystal was also analyzed using the TGA/DTG technique.
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The Çanakkale Onsekiz Mart University Grants Commission for a research grant (Project Number: 2016/672), Çanakkale Onsekiz Mart University, 17100, Çanakkale, Turkey.
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DOI Link: https://doi.org/10.5155/eurjchem.14.3.376-384.2462
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