European Journal of Chemistry 2019, 10(4), 386-402 | doi: https://doi.org/10.5155/eurjchem.10.4.386-402.1921 | Get rights and content






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


Aysegul Suzan Polat (1,*) orcid , Ilkay Gumus (2) orcid , Hakan Arslan (3) orcid

(1) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, 33343, Turkey
(2) Department of Basic Sciences, Faculty of Maritime, Mersin University, Mersin, 33343, Turkey
(3) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, 33343, Turkey
(*) Corresponding Author

Received: 02 Sep 2019 | Revised: 22 Oct 2019 | Accepted: 26 Oct 2019 | Published: 31 Dec 2019 | Issue Date: December 2019

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.


Keywords


Vibration spectrum; Ab initio calculations; Infrared spectroscopy; Redox active compound; Density functional theory; Hirshfeld surface analysis

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DOI: 10.5155/eurjchem.10.4.386-402.1921

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Funding information


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

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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Polat, A.; Gumus, I.; Arslan, H. Eur. J. Chem. 2019, 10(4), 386-402. doi:10.5155/eurjchem.10.4.386-402.1921
Polat, A.; 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(4), 386-402. doi:10.5155/eurjchem.10.4.386-402.1921
Polat, A., Gumus, I., & Arslan, H. (2019). Vibrational spectroscopic and Hirshfeld surface analysis of N,N'-(azanediylbis(2,1-phenylene))bis(2-chloropropanamide). European Journal of Chemistry, 10(4), 386-402. doi:10.5155/eurjchem.10.4.386-402.1921
Polat, Aysegul, Ilkay Gumus, & Hakan Arslan. "Vibrational spectroscopic and Hirshfeld surface analysis of N,N'-(azanediylbis(2,1-phenylene))bis(2-chloropropanamide)." European Journal of Chemistry [Online], 10.4 (2019): 386-402. Web. 20 Jan. 2020
Polat, Aysegul, Gumus, Ilkay, AND Arslan, Hakan. "Vibrational spectroscopic and Hirshfeld surface analysis of N,N'-(azanediylbis(2,1-phenylene))bis(2-chloropropanamide)" European Journal of Chemistry [Online], Volume 10 Number 4 (31 December 2019)

DOI Link: https://doi.org/10.5155/eurjchem.10.4.386-402.1921

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