Experimental and DFT-based investigation of structural, spectroscopic, and electronic features of 6-Chloroquinoline

Year 2023, Volume: 19 Issue: 3, 271 - 281, 30.09.2023

Etem Kose , Fehmi Bardak

https://doi.org/10.18466/cbayarfbe.1313229

Abstract

In this study, molecular structure, spectroscopic, and electronic features of 6-chloroquinoline were studied via experimental techniques of FT-IR, UV-Vis, 1H and 13C NMR and electronic structure theory calculations with DFT/B3LYP method and 6-311++G(d,p) basis set combination. The vibrational modes were assigned based on the potential energy distributions through the VEDA program. The gauge-invariant atomic orbital method was utilized to obtain nuclear magnetic resonance properties and chemical shifts and provided in comparison to the experimental data. Frontier molecular orbital properties and electronic absorption spectral properties, hence UV-Vis spectrum, were obtained by TD-DFT modeling. The chemical reactivity of the compound was explored based on frontier molecular orbital properties, molecular electrostatic potential surface characteristics, and atomic charge analysis. It has been achieved that the chlorine substitution significantly alters the reactive nature of quinoline moiety.

Keywords

6-chloroquinoline, DFT, IR, NMR

Supporting Institution

Manisa Celal Bayar University Research Projects Coordination Office

Project Number

FBE–2017/139, FBE-2011/070, and FBE-2017/148)

Thanks

This study has been supported by the Manisa Celal Bayar University Research Projects Coordination Office through Project Grant Number: FBE–2017/139, FBE-2011/070, and FBE-2017/148). The numerical calculations reported in this paper were fully/partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).

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