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

Aysegul Suzan Polat; Ilkay Gumus; Hakan Arslan

doi:10.5155/eurjchem.10.4.386-402.1921

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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 2019-10-12
Published 2019-12-31

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) (L^NNN) 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 L^NNN have been recorded in the regions 4000-525 cm^-1and 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 L^NNN 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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