Calculation of Electronic Properties of Some 4-Nitroaniline Derivatives: Molecular Structure and Solvent Effects

Obi-Egbedi, N.O.; Targema, Msugh; Adeoye, Moriam Dasola; Gbangban, S. T.

doi:10.9734/irjpac/2015/18195

Cited by 5 publications

(5 citation statements)

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“…The aniline, nitrobenzene, meta nitroaniline, and para nitroaniline molecules were chosen since nitro and amino groups are well known as very strong electron-attracting [24] and donating [25] substituents, respectively. Thus, intramolecular interactions between them have been the subject of numerous studies [26][27][28][29][30]. Hence, they may be an excellent probe for studying the environmental impact on their mutual interactions.…”

Section: Introductionmentioning

confidence: 99%

Solvent influence on intramolecular interactions and aromaticity in meta and para nitroanilines

2020

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Theoretical density functional theory (B3LYP/6-31G**) was used to study the intra- and intermolecular interactions of nitrobenzene, aniline, and meta and para nitroaniline in various solvation models. The studied molecules were solvated by one or two water molecules in the presence of continuum solvation (the PCM model) or without it. Finally, the studied molecules were surrounded by a cluster of water molecules. For comparison, calculations were also made for separated molecules. Geometries, energies, hydrogen bonding between solutes and solvent molecules, atomic charges, and aromaticity were examined. The analysis was based on the Atoms in Molecules methodology and the Harmonic Oscillator Model of Aromaticity (HOMA) index. As a result, an extensive description of the solvation of nitro and amino groups and the effect of solvation on mutual interactions between these groups in meta and para nitroanilines is provided. It was found that in general, the PCM description of the hydration effect on the electronic structure of the studied systems (substituents) is consistent with the approach taking into account all individual interactions (cluster model).

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Section: Introductionmentioning

confidence: 99%

Solvent influence on intramolecular interactions and aromaticity in meta and para nitroanilines

2020

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“…The variation of energy gap with dipole moment, polarizability and hyperpolarizability agrees with the expected trend. The lower the energy gap, the higher the dipole moment, polarizability and hyperpolarizability 26 , 56 . Analysis of the result showed that compound 1 has lower energy gap, higher dipole moment, higher polarizability and hyperpolarizability compared to 2 .…”

Section: Resultsmentioning

confidence: 99%

Crystal, spectroscopic and quantum mechanics studies of Schiff bases derived from 4-nitrocinnamaldehyde

Ani

Ibeji

Obasi

et al. 2021

Sci Rep

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Two Schiff bases, (E)-1-(4-methoxyphenyl)-N-((E)-3-(4-nitrophenyl)allylidene)methanamine (compound 1) and (E)-N-((E)-3-(4-nitrophenyl)allylidene)-2-phenylethanamine (compound 2) have been synthesized and characterized using spectroscopic methods; time of flight MS, 1H and 13C NMR, FT-IR, UV–VIS, photoluminescence and crystallographic methods. The structural and electronic properties of compounds 1 and 2 in the ground state were also examined using the DFT/B3LYP functional and 6-31 + G(d,p) basis set, while the electronic transitions for excited state calculations were carried out using the TD-DFT/6-31 + G(d,p) method. The Schiff base compounds, 1 and 2 crystallized in a monoclinic crystal system and the P21/c space group. The emission spectra of the compounds are attributed to conjugated π-bond interaction while the influence of the intra-ligand charge transfer resulted in a broad shoulder for 1 and a double emission peak for 2. The calculated transitions at 450 and 369 nm for 1 and 2 respectively are in reasonable agreement with the experimental results. The higher values of dipole moment, linear polarizability and first hyperpolarizability of 1, suggest a better optical property and better candidate for the development of nonlinear optical (NLO) materials.

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“…Tables 1a, 1b and 1c show some selected values of bond lengths and bond angles calculated at DFT/b3lyp level using 6-31++(d,p) and 6-311++(d,p) basis sets for the studied molecules. The bond length is the measurement of the distance between two covalently bonded atoms [18]. The bond energy of the molecules with small bond angles and bond length is higher than that of the one with large bond length and bond angles.…”

Section: Optimized Parametersmentioning

confidence: 99%

“…These properties of materials are important in determining their potentials in electronic and photonic applications. Molecules with a large value of NLO are classified as important materials for photonic applications [18]. Dipole moment is the property that describes the polarity of a molecule [25].…”

Section: Non-linear Optical (Nlo) Propertiesmentioning

confidence: 99%

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Density Functional Theory Investigation of the Doping Effects of Bromine and Fluorine on the Electronic and Optical Properties of Neutral and Ionic Perylene

Abubakar

Suleiman²,

Gidado

2021

PSIJ

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Perylene and its derivatives are some of the promising organic semiconductors. They have found vast applications in many areas such as photovoltaic systems, organic light-emitting diodes, and so on. The instability of organic molecules under ambient conditions is one factor deterring the commercialization of organic semiconductor devices. Currently, most of the investigation of Perylene and its derivatives concentrated on its diimide and bisimide derivatives. In this work, an investigation of the effects of doping Bromine and Fluorine on the electronic and non-linear optical properties was carried out based on Density Functional Theory (DFT) as implemented in the Gaussian 09 software package. We computed the Molecular geometries of the molecules, HOMO-LUMO energy gap, global chemical indices and non-linear optical properties using the same method. The bond lengths and angles of the mono-halogenated molecules at different charge states were found to be less than that of the isolated Perylene. 1-fluoroperylene was found to be the most stable amongst the studied molecule for having the least bond angles and bond lengths. In the calculation of the energy bandgap neutral 1-fluoroperylene was observed to have the highest energy gap 3.0414 eV and 3.0507 eV for 6-31++G(d,p) and 6-311++G(d,p) basis sets respectively. These results were found to agree with the existing literature. This reconfirmed 1-fluoroperylene as the most stable molecule. The computations of the ionic molecules reported small values of the energy gap. The molecule with the most chemical hardness was obtained to be the neutral 1-fluoroperylene with a chemical hardness of 1.5253eV. All the ionic molecules results were found to be more reactive than their neutral form for having lower values of chemical hardness. For NLO calculations, the results showed an increment in their values with the ionic hybrid molecules having the largest values. In the case of first-order hyper-polarizability, 1-bromoperylene (neutral), 1-fluoroperylene (neutral), 1-bromoperylene (anionic), 1-fluoroperylene (anionic), 1-bromoperylene (cationic) and 1-fluoroperylene (cationic) were found to be 73.93%, 1.71%, 83.9%, 39.2%,38.7% and 41.7% larger than that of Urea respectively. These calculated results make these hybrid molecules suitable for a wide range of optoelectronic applications.

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Calculation of Electronic Properties of Some 4-Nitroaniline Derivatives: Molecular Structure and Solvent Effects

Cited by 5 publications

References 0 publications

Solvent influence on intramolecular interactions and aromaticity in meta and para nitroanilines

Solvent influence on intramolecular interactions and aromaticity in meta and para nitroanilines

Crystal, spectroscopic and quantum mechanics studies of Schiff bases derived from 4-nitrocinnamaldehyde

Density Functional Theory Investigation of the Doping Effects of Bromine and Fluorine on the Electronic and Optical Properties of Neutral and Ionic Perylene

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