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
Autori
Vitnik, VesnaVitnik, Željko
Banjac, Nebojša
Valentić, Nataša
Ušćumlić, Gordana
Juranić, Ivan
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
1-(4-Chloro-phenyl)-3-phenyl-succinimide / Vibrational spectra / NMR / UV-Vis / NBO / TD-DFTIzvor:
Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 2014, 117, 42-53Izdavač:
- Pergamon-Elsevier Science Ltd, Oxford
Finansiranje / projekti:
- High-Performance Computing Infrastructure for South East Europe's Research Communities (EU-FP7-261499)
- Racionalni dizajn i sinteza biološki aktivnih i koordinacionih jedinjenja i funkcionalnih materijala, relevantnih u (bio)nanotehnologiji (RS-MESTD-Basic Research (BR or ON)-172035)
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (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
Institucija/grupa
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 . .