Synthesis and Reactivities of Triphenyl Acetamide Analogs for Potential Nonlinear Optical Material Uses

israr, hira; Rasool, Nasır; Hashmı, Muhammad Alı; Mahmood, Tariq; Rashid, Umer; Hussein, Mohd Zobir; Akhtar, Muhammad Nadeem

doi:10.3390/sym11050622

Cited by 10 publications

(6 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The DFT computations are also a source of other important information, including some important chemical reactivity descriptors, as shown in Table 5. These chemical reactivity descriptors have been calculated from the energies of HOMO and LUMO by the equations previously described by us in [24]. The predicted reactivity of the compounds 9c, 9g, and 9h are confirmed by the reactivity descriptors, as shown in Table 5.…”

Section: Conceptual Dft Reactivity Descriptorsmentioning

confidence: 65%

Synthesis of Functionalized Thiophene Based Pyrazole Amides via Various Catalytic Approaches: Structural Features through Computational Applications and Nonlinear Optical Properties

et al. 2022

Self Cite

View full text Add to dashboard Cite

In the present study, pyrazole-thiophene-based amide derivatives were synthesized by different methodologies. Here, 5-Bromothiophene carboxylic acid (2) was reacted with substituted, unsubstituted, and protected pyrazole to synthesize the amide. It was observed that unsubstituted amide (5-bromo-N-(5-methyl-1H-pyrazol-3-yl)thiophene-2-carboxamide (7) was obtained at a good yield of about 68 percent. The unsubstituted amide (7) was arylated through Pd (0)-catalyzed Suzuki–Miyaura cross-coupling, in the presence of tripotassium phosphate (K3PO4) as a base, and with 1,4-dioxane as a solvent. Moderate to good yields (66–81%) of newly synthesized derivatives were obtained. The geometry of the synthesized compounds (9a–9h) and other physical properties, like non-linear optical (NLO) properties, nuclear magnetic resonance (NMR), and other chemical reactivity descriptors, including the chemical hardness, electronic chemical potential, ionization potential, electron affinity, and electrophilicity index have also been calculated for the synthesized compounds. In this study, DFT calculations have been used to investigate the electronic structure of the synthesized compounds and to compute their NMR data. It was also observed that the computed NMR data manifested significant agreement with the experimental NMR results. Furthermore, compound (9f) exhibits a better non-linear optical response compared to all other compounds in the series. Based on frontier molecular orbital (FMO) analysis and the reactivity descriptors, compounds (9c) and (9h) were predicted to be the most chemically reactive, while (9d) was estimated to be the most stable among the examined series of compounds.

show abstract

Section: Conceptual Dft Reactivity Descriptorsmentioning

confidence: 65%

Synthesis of Functionalized Thiophene Based Pyrazole Amides via Various Catalytic Approaches: Structural Features through Computational Applications and Nonlinear Optical Properties

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…The calculation of these electronic properties have been reported widely in the literature [ 23 , 24 , 25 , 26 , 27 ]. Ionization potential ( I ), electron affinity ( A ), chemical hardness ( ƞ ), and electronic chemical potential ( μ ) have been computed on the basis of Koopman’s theorem according to the formulas described previously by us [ 28 ]. The values of all these descriptors are presented in the Table 2 .…”

Section: Resultsmentioning

confidence: 99%

Palladium(0) Catalyzed Synthesis of (E)-4-Bromo-N-((3-bromothiophen-2-yl)methylene)-2-methylaniline Derivatives via Suzuki Cross-Coupling Reaction: An Exploration of Their Non-Linear Optical Properties, Reactivity and Structural Features

et al. 2021

Self Cite

View full text Add to dashboard Cite

A series of (E)-4-bromo-N-((3-bromothiophen-2-yl)methylene)-2-methylaniline analogs synthesized in considerable yields through Suzuki cross-coupling reactions. Various electron donating and withdrawing functional moieties were successfully incorporated under the employed reaction conditions. Reaction of 4-bromo-2-methylaniline (1) with 3-bromothiophene-2-carbaldehyde (2b) in the existence of glacial acetic acid, provided (E)-4-bromo-N-((3-bromothiophen-2-yl)methylene)-2-methylaniline (3b) in excellent yield (94%). Suzuki coupling of 3b with different boronic acids in the presence of Pd(PPh3)4/K3PO4 at 90 °C led to the synthesis of the monosubstituted and bisubstituted products 5a–5d and 6a–6d in moderate yields (33–40% and 31–46%, respectively). Density functional theory (DFT) investigations were performed on different synthesized analogues 5a–5d, 6a–6d to determine their structural characteristics. The calculations provide insight into the frontier molecular orbitals (FMOs) of the imine-based analogues and their molecular electrostatic potential (MESP). Reactivity descriptors like ionization energy (I), electron affinity (A), chemical hardness (ƞ) and index of nucleophilicity have been calculated for the first time for the synthesized molecules.

show abstract

“…Different electronic properties, including ionization potential (I.P); electron affinity (E.A); and chemical hardness, softness, and electronegativity (E.N) of compounds 1 and 2 , were computed for the first time at the PBE0/def2‐TZVP level, and the values are listed in Table S13. The detailed calculation method of these properties is also given in S16 in the supporting information . Negative HOMO value corresponds to ionization potential and has a value of 6.37 and 6.38 eV for compounds 1 and 2 , respectively.…”

Section: Resultsmentioning

confidence: 99%

A profound density functional theory study to unravel the spectroscopic and molecular properties of two Flavanols differing in α‐pyrone ring position

Hashmı

Farooq

Bibi

et al. 2019

J Chinese Chemical Soc

Self Cite

View full text Add to dashboard Cite

A comprehensive theoretical model was designed for two new flavanols that have been reported from Glycosmis pentaphylla, differing in the placement of α-pyrone ring. The density functional theory (DFT) approach was utilized for computing different properties of these compounds to validate the experimental findings and stereochemical assignments. Electronic properties, geometric parameters, frontier molecular orbitals (FMOs), molecular electrostatic potential (MESP), and natural bond orbital analysis were performed for the first time at the PBE0-D3BJ/def2-TZVP level of theory for the compounds under study. The simulated vibrational frequencies for compounds 1 and 2 were computed and compared with the experimental results. nuclear magnetic resonance (NMR) ( 1 H and 13 C) chemical shift values were computed at the PBE0-D3BJ/ def2-TZVP/SMD DMSO level of theory and showed a very good agreement with the experimental results for both the compounds. The electronic circular dichroism (ECD) and ultraviolet-visible (UV) spectra for both the compounds were obtained using timedependent DFT in methanol, whose results exhibited excellent correlation with experimental data. The intermolecular interaction effect on geometric parameters, vibrational frequencies, and electronic properties were studied for the first time. K E Y W O R D S density functional theory, flavanols, HOMO-LUMO

show abstract

Synthesis and Reactivities of Triphenyl Acetamide Analogs for Potential Nonlinear Optical Material Uses

Cited by 10 publications

References 48 publications

Synthesis of Functionalized Thiophene Based Pyrazole Amides via Various Catalytic Approaches: Structural Features through Computational Applications and Nonlinear Optical Properties

Synthesis of Functionalized Thiophene Based Pyrazole Amides via Various Catalytic Approaches: Structural Features through Computational Applications and Nonlinear Optical Properties

Palladium(0) Catalyzed Synthesis of (E)-4-Bromo-N-((3-bromothiophen-2-yl)methylene)-2-methylaniline Derivatives via Suzuki Cross-Coupling Reaction: An Exploration of Their Non-Linear Optical Properties, Reactivity and Structural Features

A profound density functional theory study to unravel the spectroscopic and molecular properties of two Flavanols differing in α‐pyrone ring position

Contact Info

Product

Resources

About