Computational Insights on Molecular Structure, Electronic Properties, and Chemical Reactivity of (E)-3-(4-Chlorophenyl)-1-(2-Hydroxyphenyl)Prop-2-en-1-one

In the current examination, (E)-3-(4-chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one has been studied to investigate geometrical entities, electronic properties, and chemical reactivity viewpoints. To inspect structural, spectroscopic, and chemical reactivity aspects, density functional theory method (DFT) at B3LYP/6-311G(d,p) basis set has been employed. The (E)-3-(4-chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one has been synthesized and characterized by FT-IR, 1HNMR, and 13C NMR spectral techniques. The detailed investigation of bond lengths and bond angles is discussed to comprehend the geometrical framework. To explore its chemical behaviour, Mulliken atomic charges, molecular electrostatic potential surface, and electronic parameters are introduced. The imperative exploration of the electronic properties, such as HOMO and LUMO energies, was studied by the time-dependent DFT (TD-DFT) method. The dipole moment of the title molecule is 2.57 Debye with C1 point group symmetry. The most electropositive carbon and hydrogen atoms in the title molecule are C14 and H27 respectively. Amongst aromatic C=C, the C16-C18 is the longest, and C17-C19 is the shortest bond. The molecular electrostatic potential plot predicts the positive electrostatic potential is around hydrogen atoms. The vibrational assignments were made by comparing the experimental FT-IR absorption peaks with the scaled frequencies obtained using computational work. Besides, some significant thermochemical information is obtained using the same basis set using frequencies.

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Experimental and Theoretical Studies on the Molecular Structure, FT-IR, NMR, HOMO, LUMO, MESP, and Reactivity Descriptors of (E)-1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

Material Science Research India ◽

10.13005/msri.17.special-issue1.07 ◽

2020 ◽

Vol 17 (SpecialIssue1) ◽

pp. 54-72

Author(s):

Rahul Ashok Shinde ◽

Vishnu A shok Adole ◽

Bapu Sonu Jagdale ◽

Thansing Bhavsing Pawar

Keyword(s):

Molecular Structure ◽

Electrostatic Potential ◽

Density Functional ◽

Dft Method ◽

Basis Set ◽

Group Symmetry ◽

Ir Absorption ◽

Hydrogen Atoms ◽

Reactivity Descriptors ◽

Ft Ir

The present research deals with the synthesis, characterization and density functional theory (DFT) study of (E)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (DTMPP). For the computational investigation, DFT method at B3LYP/6-311++G(d,p) basis set has been used. Herein, structural properties like molecular structure, bond lengths, and bond angles of the DTMPP have been explored. The all-important examination of the electronic properties; HOMO and LUMO energies were studied by the time-dependent DFT (TD-DFT) method. The experimental and theoretical spectroscopic Investigation on FT-IR, 1HNMR, 13C NMR has been unveiled in the present research. To study the chemical behaviour of the DTMPP, Mulliken atomic charges, molecular electrostatic surface potential, and reactivity descriptors have been explored. The dipole moment of the DTMPP is 1.27 Debye with C1 point group symmetry and -1225.77 a.u. E(B3LYP) energy. The most electropositive carbon and hydrogen atoms in the DTMPP are C14 and H27 respectively. The C1-C6 bond is the longest (1.4089 Å) C=C bond in the DTMPP. The oxygen atom O33 is having short contact interaction with the hydrogen atom H44 with a distance of 3.3258 Å. The molecular electrostatic potential plot predicts the positive electrostatic potential is around hydrogen atoms. The FT-IR assignments were made by comparing the experimental FT-IR absorption peaks with the scaled frequencies obtained using DFT method. Furthermore, some valuable insights on thermochemical data are obtained using the harmonic frequencies at same basis set.

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Chemical Reactivity, Dipole Moment and First Hyperpolarizability of Aristolochic Acid I

Journal of Institute of Science and Technology ◽

10.3126/jist.v21i1.16030 ◽

2016 ◽

Vol 21 (1) ◽

pp. 1-9 ◽

Cited By ~ 3

Author(s):

Bhawani Datta Joshi

Keyword(s):

Dipole Moment ◽

Electrostatic Potential ◽

Density Functional ◽

Molecular Electrostatic Potential ◽

Aristolochic Acid ◽

Chemical Reactivity ◽

Basis Set ◽

Non Linear ◽

Linear Optical ◽

Aristolochic Acid I

Aristolochic acids (AAs) have been used in the treatment of oedema in Chinese herb medicine since long ago. In this paper, molecular electrostatic potential, chemical reactivity and non linear optical properties of aristolochic acid I (AA I) have been analyzed using density functional theory employing 6-311++G(d,p) basis set. The chemical reactivity of the molecule has been explained with the help of chemical reactivity descriptors, molar refractivity and the molecular electrostatic potential surface (ESP). The calculated dipole moment and first order hyperpolarizability show that the molecule possesses non-linear optical property.Journal of Institute of Science and TechnologyVolume 21, Issue 1, August 2016, page: 1-9

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Investigation of Some Antiviral N-Heterocycles as COVID 19 Drug: Molecular Docking and DFT Calculations

International Journal of Molecular Sciences ◽

10.3390/ijms21113922 ◽

2020 ◽

Vol 21 (11) ◽

pp. 3922 ◽

Cited By ~ 19

Author(s):

Mohamed Hagar ◽

Hoda A. Ahmed ◽

Ghadah Aljohani ◽

Omaima A. Alhaddad

Keyword(s):

Dipole Moment ◽

Molecular Docking ◽

Dft Calculations ◽

Binding Affinity ◽

Electrostatic Potential ◽

Density Functional ◽

Molecular Electrostatic Potential ◽

Hydrophobic Interactions ◽

Chemical Reactivity ◽

Main Protease

The novel coronavirus, COVID-19, caused by SARS-CoV-2, is a global health pandemic that started in December 2019. The effective drug target among coronaviruses is the main protease Mpro, because of its essential role in processing the polyproteins that are translated from the viral RNA. In this study, the bioactivity of some selected heterocyclic drugs named Favipiravir (1), Amodiaquine (2), 2′-Fluoro-2′-deoxycytidine (3), and Ribavirin (4) was evaluated as inhibitors and nucleotide analogues for COVID-19 using computational modeling strategies. The density functional theory (DFT) calculations were performed to estimate the thermal parameters, dipole moment, polarizability, and molecular electrostatic potential of the present drugs; additionally, Mulliken atomic charges of the drugs as well as the chemical reactivity descriptors were investigated. The nominated drugs were docked on SARS-CoV-2 main protease (PDB: 6LU7) to evaluate the binding affinity of these drugs. Besides, the computations data of DFT the docking simulation studies was predicted that the Amodiaquine (2) has the least binding energy (−7.77 Kcal/mol) and might serve as a good inhibitor to SARS-CoV-2 comparable with the approved medicines, hydroxychloroquine, and remdesivir which have binding affinity −6.06 and −4.96 Kcal/mol, respectively. The high binding affinity of 2 was attributed to the presence of three hydrogen bonds along with different hydrophobic interactions between the drug and the critical amino acids residues of the receptor. Finally, the estimated molecular electrostatic potential results by DFT were used to illustrate the molecular docking findings. The DFT calculations showed that drug 2 has the highest of lying HOMO, electrophilicity index, basicity, and dipole moment. All these parameters could share with different extent to significantly affect the binding affinity of these drugs with the active protein sites.

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Basis set dependence of the molecular electrostatic potential topography. A case study of substituted benzenes

Chemical Physics Letters ◽

10.1016/0009-2614(95)00473-h ◽

1995 ◽

Vol 239 (4-6) ◽

pp. 273-281 ◽

Cited By ~ 38

Author(s):

Shridhar R. Gadre ◽

Sudhir A. Kulkarni ◽

C.H. Suresh ◽

Indira H. Shrivastava

Keyword(s):

Electrostatic Potential ◽

Molecular Electrostatic Potential ◽

Basis Set ◽

Substituted Benzenes

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Theoretical Evaluation on The Interaction Between Triglycerides and Methylxanthines Using Density Functional Theory B3LYP/6-31G(d,p) and Molecular Electrostatic Potential

Asian Journal of Chemistry ◽

10.14233/ajchem.2021.22978 ◽

2020 ◽

Vol 33 (1) ◽

pp. 171-178

Author(s):

N.F.M. Azmi ◽

R. Ali ◽

A.A. Azmi ◽

M.Z.H. Rozaini ◽

K.H.K. Bulat ◽

...

Keyword(s):

Density Functional Theory ◽

Hydrogen Bond ◽

Electrostatic Potential ◽

Density Functional ◽

Molecular Electrostatic Potential ◽

Basis Set ◽

Individual Species ◽

Interaction Energies ◽

Binding Interaction ◽

Functional Theory

The binding, interaction and distortion energies between the main triglycerides, palmitic-oleic-stearic (POS) in cocoa butter versus palmitic-oleic-palmitic (POP) in refined, bleached and deodorized (RBD) palm oil with cocoa′s methylxanthines (caffeine, theobromine, and theophylline) during the production of chocolate were theoretically studied and reported. The quantum mechanical software package of Gaussian09 at the theoretical level of density functional theory B3LYP/6-31G(d,p) was employed for all calculations, optimization, and basis set superposition errors (BSSE). Geometry optimizations were carried out to the minimum potential energy of individual species and binary complexes formed between the triglycerides, methylxanthines and polyphenols. The interaction energies for the optimized complexes were then corrected for the BSSE using the counterpoise method of Boys and Bernardi. The results revealed that the binding energy and interaction energy between methylxanthine components in cocoa powder with triglycerides were almost of the same magnitude (13.6-14.5 and 3.4-3.7 kJ/mol, respectively), except for the binary complex of POS-caffeine (25.1 and 10.7 kJ/mol, respectively). Based on the molecular geometry results, the hydrogen bond length and angle correlated well with the interaction energies. Meanwhile, the POS-caffeine complex with two higher and almost linear bond angles showed higher binding and interaction energies as compared to the other methylxanthines. Therefore, a donor-acceptor analysis showed that the hydrogen bond strength was proven using the molecular electrostatic potential (MEP), which resulted in parallel outcomes. The research results were believed to be one of the factors that contributed to the rheological behaviour and sensory perception of cocoa products, especially chocolate.

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