Quntum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide
2014
Authors
Vitnik, VesnaVitnik, Željko
Banjac, Nebojša
Valentić, Nataša
Ušćumlić, Gordana
Juranić, Ivan
Article (Published version)
Metadata
Show full item recordAbstract
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-DFTSource:
Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 2014, 117, 42-53Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- High-Performance Computing Infrastructure for South East Europe's Research Communities (EU-FP7-261499)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-MESTD-Basic Research (BR or ON)-172035)
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1016/j.saa.2013.07.099
ISSN: 1386-1425
PubMed: 23981413
WoS: 000328179900006
Scopus: 2-s2.0-84884511785
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Vitnik, Vesna AU - Vitnik, Željko AU - Banjac, Nebojša AU - Valentić, Nataša AU - Ušćumlić, Gordana AU - Juranić, Ivan PY - 2014 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2792 AB - 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. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy T1 - Quntum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide EP - 53 SP - 42 VL - 117 DO - 10.1016/j.saa.2013.07.099 ER -
@article{ author = "Vitnik, Vesna and Vitnik, Željko and Banjac, Nebojša and Valentić, Nataša and Ušćumlić, Gordana and Juranić, Ivan", year = "2014", 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.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy", title = "Quntum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide", pages = "53-42", volume = "117", doi = "10.1016/j.saa.2013.07.099" }
Vitnik, V., Vitnik, Ž., Banjac, N., Valentić, N., Ušćumlić, G.,& Juranić, I.. (2014). Quntum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy Pergamon-Elsevier Science Ltd, Oxford., 117, 42-53. https://doi.org/10.1016/j.saa.2013.07.099
Vitnik V, Vitnik Ž, Banjac N, Valentić N, Ušćumlić G, Juranić I. Quntum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2014;117:42-53. doi:10.1016/j.saa.2013.07.099 .
Vitnik, Vesna, Vitnik, Željko, Banjac, Nebojša, Valentić, Nataša, Ušćumlić, Gordana, Juranić, Ivan, "Quntum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 117 (2014):42-53, https://doi.org/10.1016/j.saa.2013.07.099 . .