Nuclear magnetic resonance, vibrational spectroscopic studies, physico-chemical properties and computational calculations on (nitrophenyl) octahydroquinolindiones by DFT method

M A Pasha; Aisha Siddekha; Soni Mishra; Sadeq Hamood Saleh Azzam; S Umapathy

doi:10.1016/j.saa.2014.09.021

Nuclear magnetic resonance, vibrational spectroscopic studies, physico-chemical properties and computational calculations on (nitrophenyl) octahydroquinolindiones by DFT method

Spectrochim Acta A Mol Biomol Spectrosc. 2015 Feb 5:136 Pt B:221-33. doi: 10.1016/j.saa.2014.09.021. Epub 2014 Oct 5.

Authors

M A Pasha¹, Aisha Siddekha², Soni Mishra³, Sadeq Hamood Saleh Azzam⁴, S Umapathy³

Affiliations

¹ Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore 560001, India. Electronic address: m_af_pasha@ymail.com.
² Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore 560001, India; Department of Chemistry, Smt. VHD Central Institute of Home Science, Bangalore 560001, India.
³ Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560012, India.
⁴ Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore 560001, India.

PMID: 25440584
DOI: 10.1016/j.saa.2014.09.021

Abstract

In the present study, 2'-nitrophenyloctahydroquinolinedione and its 3'-nitrophenyl isomer were synthesized and characterized by FT-IR, FT-Raman, (1)H NMR and (13)C NMR spectroscopy. The molecular geometry, vibrational frequencies, (1)H and (13)C NMR chemical shift values of the synthesized compounds in the ground state have been calculated by using the density functional theory (DFT) method with the 6-311++G (d,p) basis set and compared with the experimental data. The complete vibrational assignments of wave numbers were made on the basis of potential energy distribution using GAR2PED programme. Isotropic chemical shifts for (1)H and (13)C NMR were calculated using gauge-invariant atomic orbital (GIAO) method. The experimental vibrational frequencies, (1)H and (13)C NMR chemical shift values were found to be in good agreement with the theoretical values. On the basis of vibrational analysis, molecular electrostatic potential and the standard thermodynamic functions have been investigated.

Keywords: Computational studies; DFT; NMR; Octahydroquinolinediones; Raman spectroscopy; Vibrational spectroscopy.

MeSH terms

Chemical Phenomena*
Isomerism
Magnetic Resonance Spectroscopy*
Models, Molecular*
Molecular Conformation
Quantum Theory*
Quinolones / chemistry*
Spectroscopy, Fourier Transform Infrared
Spectrum Analysis, Raman*
Static Electricity
Thermodynamics
Vibration*

Substances

Quinolones