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
Аутори
Vitnik, VesnaVitnik, Željko
Banjac, Nebojša R.
Valentić, Nataša V.
Ušćumlić, Gordana
Juranić, Ivan
Чланак у часопису (Рецензирана верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
1-(4-Chloro-phenyl)-3-phenyl-succinimide / Vibrational spectra / NMR / UV-Vis / NBO / TD-DFTИзвор:
Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 2014, 117, 42-53Издавач:
- Oxford : Pergamon-Elsevier Science Ltd
Финансирање / пројекти:
- Рационални дизајн и синтеза биолошки активних и координационих једињења и функционалних материјала, релевантних у (био)нанотехнологији (RS-MESTD-Basic Research (BR or ON)-172035)
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
- High-Performance Computing Infrastructure for South East Europe's Research Communities (EU-FP7-261499)
Напомена:
- 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
Институција/група
IHTMTY - JOUR AU - Vitnik, Vesna AU - Vitnik, Željko AU - Banjac, Nebojša R. AU - Valentić, Nataša V. AU - Ušćumlić, Gordana AU - Juranić, Ivan PY - 2014 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3160 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 - Oxford : Pergamon-Elsevier Science Ltd T2 - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy T1 - 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 VL - 117 SP - 42 EP - 53 DO - 10.1016/j.saa.2013.07.099 ER -
@article{ author = "Vitnik, Vesna and Vitnik, Željko and Banjac, Nebojša R. and Valentić, Nataša V. 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 = "Oxford : Pergamon-Elsevier Science Ltd", journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy", title = "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", volume = "117", pages = "42-53", doi = "10.1016/j.saa.2013.07.099" }
Vitnik, V., Vitnik, Ž., Banjac, N. R., Valentić, N. V., Ušćumlić, G.,& Juranić, I.. (2014). 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. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy Oxford : Pergamon-Elsevier Science Ltd., 117, 42-53. https://doi.org/10.1016/j.saa.2013.07.099
Vitnik V, Vitnik Ž, Banjac NR, Valentić NV, Ušćumlić G, Juranić I. 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. 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 R., Valentić, Nataša V., Ušćumlić, Gordana, Juranić, Ivan, "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" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 117 (2014):42-53, https://doi.org/10.1016/j.saa.2013.07.099 . .