Crystal structure and vibrational spectra of bis(2-isobutyrylamidophenyl)amine: a redox noninnocent ligand

Authors: EMRAH ASLANTATAR, SAVITA K. SHARMA, OMAR VILLANUEVA, CORA E. MACBETH, İLKAY GÜMÜŞ, HAKAN ARSLAN

Abstract: The molecular structure of bis(2-isobutyrylamidophenyl)amine (H₃L^NNN) has been determined from single-crystal X-ray diffraction data. The crystal packing of H₃L^NNN is governed by the N-H...O and C-H...O hydrogen-bonding and C-H...π stacking interactions between the vicinal molecules. The intermolecular interactions in the crystal structure of H₃L^NNN have been also examined via Hirshfeld surface analysis and fingerprint plots. The Hirshfeld surface analysis showed that the important role of N-H...O and C-H...π interactions in the solid-state structure of H₃L^NNN. The molecular structure, vibrational frequencies, and infrared intensities of H₃L^NNN were computed by ab initio HF and DFT (B3LYP, B3PW91, and BLYP) methods using the 6-31G(d,p) basis set. The computed theoretical geometric parameters were compared with the corresponding single crystal structure of H₃L^NNN. The harmonic vibrations calculated for the title compound by the B3LYP method are in good agreement with the experimental IR spectral data. The theoretical vibrational spectrum of the H₃L^NNN compound was interpreted through potential energy distributions using the SQM Version 2.0 program. The performance of the used methods and the scaling factor values were calculated with PAVF Version 1.0 program.

Keywords: Redox noninnocent ligand, single crystal structure, Hirshfeld surface analysis, infrared spectrum, ab initio calculations, Hartree?Fock method, density functional theory method

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