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Structural and spectral investigations of the recently synthesized chalcone (E)-3-mesityl-1-(naphthalen-2-yl) prop-2-en-1-one, a potential chemotherapeutic agent.

Barakat A, Al-Majid AM, Soliman SM, Mabkhot YN, Ali M, Ghabbour HA, Fun HK, Wadood A - Chem Cent J (2015)

Bottom Line: The calculated IR fundamental bands were assigned and compared with the experimental data.Molecular stability was successfully analyzed using NBO and electron delocalization is confirmed by MEP.Graphical Abstract(E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one: a crystal structure and computational studies.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, 11451 Riyadh, Saudi Arabia ; Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, 21321 Alexandria, Ibrahimia Egypt.

ABSTRACT

Background: Chalcones (1,3-diaryl-2-propen-1-ones, represent an important subgroup of the polyphenolic family, which have shown a wide spectrum of medical and industrial application. Due to their redundancy in plants and ease of preparation, this category of molecules has inspired considerable attention for potential therapeutic uses. They are also effective in vivo as anti-tumor promoting, cell proliferating inhibitors and chemo preventing agents.

Results: Synthesis and molecular structure investigation of (E)-3-mesityl-1-(naphthalen-2-yl) prop-2-en-1-one (3) is reported. The structure of the title compound 3 is confirmed by X-ray crystallography. The optimized molecular structure of the studied compound is calculated using DFT B3LYP/6-311G (d,p) method. The calculated geometric parameters are in good agreement with the experimental data obtained from our reported X-ay structure. The calculated IR fundamental bands were assigned and compared with the experimental data. The electronic spectra of the studied compound have been calculated using the time dependant density functional theory (TD-DFT). The longest wavelength band is due to H → L (79 %) electronic transition which belongs to π-π* excitation. The (1)H- and (13)C-NMR chemical shifts were calculated using gauge independent atomic orbitals (GIAO) method, which showed good correlations with the experimental data (R(2) = 0.9911-0.9965). The natural bond orbital (NBO) calculations were performed to predict the natural atomic charges at different atomic sites. The molecular electrostatic potential (MEP) was used to visualize the charge distribution on the molecule. Molecular docking results suggest that the compound might exhibit inhibitory activity against GPb and may act as potential anti-diabetic compound.

Conclusions: (E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one single crystal is grown and characterized by single crystal X-ray diffraction, FT-IR, UV-vis, DFT and optimized geometrical parameters are close to the experimental bond lengths and angles. Molecular stability was successfully analyzed using NBO and electron delocalization is confirmed by MEP. Prediction of Activity Spectra Analysis of the title compound, predicts anti-diabetic activity with probability to have an active value of 0.348. Graphical Abstract(E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one: a crystal structure and computational studies.

No MeSH data available.


Related in: MedlinePlus

The ground state isodensity surface plots for the frontier molecular orbitals
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Fig6: The ground state isodensity surface plots for the frontier molecular orbitals

Mentions: The electron densities of the frontier molecular orbitals (FMOs) were used for predicting the most reactive position in π–electron systems and to explaine several types of reactions in conjugated system [33]. The properties of these FMOs like energy are very useful for physicists and chemists. The energy values of the lowest unoccupied molecular orbital (ELUMO) and the highest occupied molecular orbital (EHOMO) and their energy gap (ΔE) reflect the chemical reactivity of the molecule. Recently the energy gap between HOMO and LUMO has been used to prove the bioactivity from intramolecular charge transfer (ICT) [34, 35]. The EHOMO, ELUMO and ΔE values for the studied compound were calculated by B3LYP/6–311G (d,p) method. The HOMO and LUMO pictures are shown in Fig. 6. It is found that the HOMO and LUMO levels are distributed mainly over the ring (π–system). The EHOMO and ELUMO are calculated to be - 6.2543 eV and −2.0458 eV respectively. The HOMO–LUMO energy gap (ΔE) represents the lowest energy electronic transition which mainly belongs to π– π* excitation (4.2085 eV).Fig. 6


Structural and spectral investigations of the recently synthesized chalcone (E)-3-mesityl-1-(naphthalen-2-yl) prop-2-en-1-one, a potential chemotherapeutic agent.

Barakat A, Al-Majid AM, Soliman SM, Mabkhot YN, Ali M, Ghabbour HA, Fun HK, Wadood A - Chem Cent J (2015)

The ground state isodensity surface plots for the frontier molecular orbitals
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4477317&req=5

Fig6: The ground state isodensity surface plots for the frontier molecular orbitals
Mentions: The electron densities of the frontier molecular orbitals (FMOs) were used for predicting the most reactive position in π–electron systems and to explaine several types of reactions in conjugated system [33]. The properties of these FMOs like energy are very useful for physicists and chemists. The energy values of the lowest unoccupied molecular orbital (ELUMO) and the highest occupied molecular orbital (EHOMO) and their energy gap (ΔE) reflect the chemical reactivity of the molecule. Recently the energy gap between HOMO and LUMO has been used to prove the bioactivity from intramolecular charge transfer (ICT) [34, 35]. The EHOMO, ELUMO and ΔE values for the studied compound were calculated by B3LYP/6–311G (d,p) method. The HOMO and LUMO pictures are shown in Fig. 6. It is found that the HOMO and LUMO levels are distributed mainly over the ring (π–system). The EHOMO and ELUMO are calculated to be - 6.2543 eV and −2.0458 eV respectively. The HOMO–LUMO energy gap (ΔE) represents the lowest energy electronic transition which mainly belongs to π– π* excitation (4.2085 eV).Fig. 6

Bottom Line: The calculated IR fundamental bands were assigned and compared with the experimental data.Molecular stability was successfully analyzed using NBO and electron delocalization is confirmed by MEP.Graphical Abstract(E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one: a crystal structure and computational studies.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, 11451 Riyadh, Saudi Arabia ; Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, 21321 Alexandria, Ibrahimia Egypt.

ABSTRACT

Background: Chalcones (1,3-diaryl-2-propen-1-ones, represent an important subgroup of the polyphenolic family, which have shown a wide spectrum of medical and industrial application. Due to their redundancy in plants and ease of preparation, this category of molecules has inspired considerable attention for potential therapeutic uses. They are also effective in vivo as anti-tumor promoting, cell proliferating inhibitors and chemo preventing agents.

Results: Synthesis and molecular structure investigation of (E)-3-mesityl-1-(naphthalen-2-yl) prop-2-en-1-one (3) is reported. The structure of the title compound 3 is confirmed by X-ray crystallography. The optimized molecular structure of the studied compound is calculated using DFT B3LYP/6-311G (d,p) method. The calculated geometric parameters are in good agreement with the experimental data obtained from our reported X-ay structure. The calculated IR fundamental bands were assigned and compared with the experimental data. The electronic spectra of the studied compound have been calculated using the time dependant density functional theory (TD-DFT). The longest wavelength band is due to H → L (79 %) electronic transition which belongs to π-π* excitation. The (1)H- and (13)C-NMR chemical shifts were calculated using gauge independent atomic orbitals (GIAO) method, which showed good correlations with the experimental data (R(2) = 0.9911-0.9965). The natural bond orbital (NBO) calculations were performed to predict the natural atomic charges at different atomic sites. The molecular electrostatic potential (MEP) was used to visualize the charge distribution on the molecule. Molecular docking results suggest that the compound might exhibit inhibitory activity against GPb and may act as potential anti-diabetic compound.

Conclusions: (E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one single crystal is grown and characterized by single crystal X-ray diffraction, FT-IR, UV-vis, DFT and optimized geometrical parameters are close to the experimental bond lengths and angles. Molecular stability was successfully analyzed using NBO and electron delocalization is confirmed by MEP. Prediction of Activity Spectra Analysis of the title compound, predicts anti-diabetic activity with probability to have an active value of 0.348. Graphical Abstract(E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one: a crystal structure and computational studies.

No MeSH data available.


Related in: MedlinePlus