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Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide

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2014
vitnik2014.pdf (930.7Kb)
Authors
Vitnik, Vesna
Vitnik, Željko
Banjac, Nebojša R.
Valentić, Nataša V.
Ušćumlić, Gordana
Juranić, Ivan
Article (Accepted Version)
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Abstract
This study represents an integrated approach towards understanding the vibrational, electronic, NMR, and structural aspects, and reactivity of 1-(4-chloro-phenyl)-3-phenyl-succinimide (CPPS). A detailed interpretation of the FT-IR, UV and NMR spectra were reported. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated with the help of density functional theory (DFT) B3LYP method using 6-31G(d,p) and 6-311++G(d,p) basis set. The scaled theoretical wave-number showed very good agreement with the experimental values. The H-1 and C-13 nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Invariant Atomic Orbital (GIAO) method. Stability of the molecule, arising from hyperconjugative interactions and charge delocalization, has been analyzed using Natural Bond Orbital (NBO) analysis. The results show that ED in the sigma* and pi* antibonding orbitals and second order delocalization energies E(2) confirm... the occurrence of intramolecular charge transfer (ICT) within the molecule. UV-Vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were calculated by Time-Dependent (TD-DFT) approach. To estimate chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of the molecule.

Keywords:
1-(4-Chloro-phenyl)-3-phenyl-succinimide / Vibrational spectra / NMR / UV-Vis / NBO / TD-DFT
Source:
Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 2014, 117, 42-53
Publisher:
  • Pergamon-Elsevier Science Ltd, Oxford
Projects:
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
  • High-Performance Computing Infrastructure for South East Europe's Research Communities (EU-261499)
Note:
  • This is a peer-reviewed version of the article: https://doi.org/10.1016/j.saa.2013.07.099
  • http://cer.ihtm.bg.ac.rs/handle/123456789/1496

DOI: 10.1016/j.saa.2013.07.099

ISSN: 1386-1425

PubMed: 23981413

WoS: 000328179900006

Scopus: 2-s2.0-84884511785
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/3160
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