European Journal of Chemistry 2022, 13(1), 49-55 | doi: https://doi.org/10.5155/eurjchem.13.1.49-55.2175 | Get rights and content

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Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of 2,2'-(((methylene-bis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenol


Goutam Kumar Patra (1,*) orcid , Dinesh De (2) orcid

(1) Department of Chemistry, Faculty of Physical Sciences, Guru Ghasidas Vishwavidyalaya, Bilaspur, Chhattisgarh, 495009, India
(2) Department of Basic Science, Vishwavidyalaya Engineering College, Ambikapur, CSVTU-Bhilai, Chhattisgarh, 497001, India
(*) Corresponding Author

Received: 07 Aug 2021 | Revised: 09 Oct 2021 | Accepted: 01 Nov 2021 | Published: 31 Mar 2022 | Issue Date: March 2022

Abstract


The synthesis, characterization, and theoretical studies of the title compound has been reported in this study. The molecular structure has been characterized by room-temperature single-crystal X-ray diffraction study which reveals that it has an angular shape with intramolecular and intermolecular hydrogen bonding. Crystal data for the title compound, C27H22N2O2 (=406.46 g/mol): monoclinic, space group C2/c (no. 15), a = 36.371(10) Å, b = 4.6031(12) Å, c = 12.192(3) Å, β = 94.972(6)°, = 2033.5(9) Å3, Z = 4, T = 100 K, μ(MoKα) = 0.084 mm-1, Dcalc = 1.328 g/cm3, 8812 reflections measured (2.248° ≤ 2Θ ≤ 49.734°), 1773 unique (Rint = 0.0323, Rsigma = 0.0239) which were used in all calculations. The final R1 was 0.0411 (I > 2σ(I)) and wR2 was 0.1165 (all data). In crystal structure, the molecule exits in the enol form and is located on a two-fold axis of symmetry; where the central methylene carbon atom of the diphenylmethane moiety is displaced from the aromatic ring planes. The Hirshfeld surface analysis of the title compound shows that H···H, C···H, and O···H interactions of 53.3, 13.2, and 5.4%; respectively, which exposed that the main intermolecular interactions were H···H intermolecular interactions. The HOMO-LUMO energy gap in the title compound is 2.9639 eV. Molecular electrostatic potential of the investigated compound has also been studied.


Keywords


H-bonding; Di-Schiff base; X-ray crystal structure; Density functional theory; Hirshfeld surface analysis; Molecular electrostatic potential

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DOI: 10.5155/eurjchem.13.1.49-55.2175

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Funding information


The Department of Science and Technology (SR/FST/CSI-264/2014 and EMR/2017/0001789) and Department of Biotechnology, Government of India, New Delhi.

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How to cite


Patra, G.; De, D. Eur. J. Chem. 2022, 13(1), 49-55. doi:10.5155/eurjchem.13.1.49-55.2175
Patra, G.; De, D. Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of 2,2'-(((methylene-bis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenol. Eur. J. Chem. 2022, 13(1), 49-55. doi:10.5155/eurjchem.13.1.49-55.2175
Patra, G., & De, D. (2022). Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of 2,2'-(((methylene-bis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenol. European Journal of Chemistry, 13(1), 49-55. doi:10.5155/eurjchem.13.1.49-55.2175
Patra, Goutam, & Dinesh De. "Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of 2,2'-(((methylene-bis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenol." European Journal of Chemistry [Online], 13.1 (2022): 49-55. Web. 18 May. 2022
Patra, Goutam, AND De, Dinesh. "Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of 2,2'-(((methylene-bis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenol" European Journal of Chemistry [Online], Volume 13 Number 1 (31 March 2022)

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