European Journal of Chemistry

Vibrational spectroscopic and Hirshfeld surface analysis of N,N'-(azanediylbis(2,1-phenylene))bis(2-chloropropanamide)

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Published: Dec 31, 2019
DOI: https://doi.org/10.5155/eurjchem.10.4.386-402.1921
Keywords:
Vibration spectrum, Ab initio calculations, Infrared spectroscopy, Redox active compound, Density functional theory, Hirshfeld surface analysis
Section
Research Article
Issue
Vol. 10 No. 4 (2019): December 2019
Dates
Received 2019-09-02
Accepted 2019-10-26
Published 2019-12-31
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Aysegul Suzan Polat
Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, 33343, Turkey
http://orcid.org/0000-0002-0281-4011
Ilkay Gumus
Department of Basic Sciences, Faculty of Maritime, Mersin University, Mersin, 33343, Turkey
http://orcid.org/0000-0002-9398-0057
Hakan Arslan
Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, 33343, Turkey
http://orcid.org/0000-0003-0046-9442

Abstract

The title molecule, N,N'-(azanediylbis(2,1-phenylene))bis(2-chloropropanamide) (LNNN) was synthesized and characterized by means of Hirshfeld surface analysis and vibrational (FT-IR and RAMAN) studies. Ab-initio Hartree-Fock (HF) and density functional theory (DFT; BLYP, B3LYP, B3PW91 and mPW1PW91) calculations were accomplished using 6-31G(d,p) and 6-311G(d,p) basis sets. The comparison of calculated bond lengths and angles with X-ray crystal structure shows sufficient agreement. The solid phase FT-IR and FT-RAMAN spectra of LNNN have been recorded in the regions 4000-525 cm-1 and 4000-50 cm-1, respectively. A comparative analysis between the calculated and experimental vibrational frequencies was carried out and significant bands were assigned. The results indicated a good correlation between experimental and theoretical IR and RAMAN frequencies. A detailed analysis of the intermolecular interactions via Hirshfeld surface analysis and fingerprint plots revealed that supramolecular structure of the LNNN is stabilized mainly by the formation of H···H, C···H, Cl···H ve O···H  intermolecular interactions.


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Polat, A. S.; Gumus, I.; Arslan, H. Vibrational Spectroscopic and Hirshfeld Surface Analysis of N,N’-(azanediylbis(2,1-phenylene) bis(2-Chloropropanamide). Eur. J. Chem. 2019, 10, 386-402.

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Supporting Agencies

This study was supported by Research Fund of Mersin University in Turkey with Project Number, 2018-1-TP2-2800.
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