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; Dinesh De

doi:10.5155/eurjchem.13.1.49-55.2175

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Published: Mar 31, 2022

DOI: https://doi.org/10.5155/eurjchem.13.1.49-55.2175

Keywords:

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

Section

Research Article

Issue

Vol. 13 No. 1 (2022): March 2022

Dates

Received 2021-08-07
Accepted 2021-11-01
Published 2022-03-31

Goutam Kumar Patra

Department of Chemistry, Faculty of Physical Sciences, Guru Ghasidas Vishwavidyalaya, Bilaspur, Chhattisgarh, 495009, India

https://orcid.org/0000-0003-3151-0284

Dinesh De

Department of Basic Science, Vishwavidyalaya Engineering College, Ambikapur, CSVTU-Bhilai, Chhattisgarh, 497001, India

https://orcid.org/0000-0001-7850-8718

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 (M =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)°, V = 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 (R_int = 0.0323, R_sigma = 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.

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Patra, G. K.; 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, 49-55.

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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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