A combined experimental and theoretical approach for structural, spectroscopic, NLO, NBO, thermal and photophysical studies of new fluorescent 5-amino-1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazole-4-carbonitrile using density functional theory

Singh, Harjinder; Singh, Arti; Khurana, Jitender M.

doi:10.1016/j.molstruc.2017.07.010

Cited by 13 publications

(6 citation statements)

References 69 publications

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“…In 3 ⋅K(18‐c‐6), the Ge−K bond is identified as the HOMO−2 with contributions from the Si(sp 3 )−Ge(sp 2 ) σ‐bond. Second order perturbation theory (SOPT) confirms strong conjugation between Ge=Si and C=N with an interaction energy of 23.6 kcal mol −1 for π GeSi →π* CN [23] . The increased Wiberg bond index (WBI) of Si1−C1 (0.904) compared to that of Si2−C1 (0.762) further corroborates this interpretation.…”

Section: Methodsmentioning

confidence: 67%

“…Second order perturbation theory (SOPT) confirms strong conjugation between Ge=Si and C=N with an interaction energy of 23.6 kcal mol À1 for p GeSi !p* CN . [23] The increased Wiberg bond index (WBI) of Si1 À C1 (0.904) compared to that of Si2 À C1 (0.762) further corroborates this interpretation. The TD-DFT simulated UV/ Vis spectrum ( Figure S31) determines the longest wavelength absorption band to l max, calc = 505 nm in good agreement with the experimental value (l max, exp = 495 nm).…”

Section: Angewandte Chemiementioning

confidence: 65%

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A Mixed Heavier Si=Ge Analogue of a Vinyl Anion

2020

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The versatile reactivities of disilenides and digermenide, heavier analogues of vinyl anions, have significantly expanded the pool of silicon and germanium compounds with various unexpected structural motifs in the past two decades. We now report the synthesis and isolation of a cyclic heteronuclear vinyl anion analogue with a Si = Ge bond, potassium silagermenide as stable thf-solvate and 18-c-6 solvate by the KC 8 reduction of germylene or digermene precursors. Its suitability as synthon for the synthesis of functional silagermenes is proven by the reactions with chlorosilane and chlorophospane to yield the corresponding silyl-and phosphanyl-silagermenes. X-ray crystallographic analysis, UV/Vis spectroscopy and DFT calculations revealed a significant degree of p-conjugation between N = C and Si = Ge double bonds in the title compound.

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Section: Methodsmentioning

confidence: 67%

Section: Angewandte Chemiementioning

confidence: 65%

A Mixed Heavier Si=Ge Analogue of a Vinyl Anion

2020

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“…In 3 ⋅K(18‐c‐6) wird die Ge−K Bindung als HOMO‐2 mit Beiträgen der Si(sp 3 )−Ge(sp 2 ) σ‐Bindung identifiziert. Störungstheorie zweiter Ordnung (SOPT) bestätigt eine starke Konjugation zwischen Ge=Si und C=N mit einer Wechselwirkungsenergie von 23.6 kcal mol −1 für π GeSi →π* CN [23] . Der im Vergleich zu Si2−C1 (0.762) erhöhte Wiberg‐Bindungsindex (WBI) von Si1−C1 (0.904) bestätigt diese Interpretation weiter.…”

Section: Methodsunclassified

“…p* CN . [23] Der im Vergleich zu Si2 À C1 (0.762) erhçhte Wiberg-Bindungsindex (WBI) von Si1 À C1 (0.904) bestätigt diese Interpretation weiter. Das simulierte TD-DFT UV/Vis Spektrum (Abbildung S31) bestimmt die Absorptionsbande mit der längsten Wellenlänge zu l max, calc = 505 nm in guter Übereinstimmung mit dem experimentellen Wert (l max, exp = 495 nm).…”

Section: Zuschriftenunclassified

Ein gemischtes, schwereres Si=Ge Analogon eines Vinylanions

2020

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Die vielseitigen Reaktivitäten von Disileniden und Digermenid, schwereren Analoga von Vinylanionen, haben den Pool an Silicium-und Germaniumverbindungen in den letzten zwei Jahrzehnten mit verschiedensten unerwarteten Strukturmotiven erheblich erweitert. Wir berichten nun über die Synthese eines cyclischen, heteronuklearen Vinylanionanalogons mit einer Si = Ge Bindung, dem Kaliumsilagermenid als stabiles THF-und 18-c-6-Solvat durch KC 8 Reduktion von Germylen-oder Digermenvorläufern. Seine Eignung als Baustein für die Synthese von funktionellen Silagermenen wird durch die jeweiligen Reaktionen mit Chlorsilan und Chlorphosphan unter Bildung der entsprechenden Silyl-und Phosphanylsilagermenen nachgewiesen. Rçntgenkristallographische Analyse, UV/Vis Spektroskopie und DFT Berechnungen zeigten einen erheblichen Grad an p-Konjugation zwischen N=C und Si=Ge Doppelbindungen in der Titelverbindung.

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“…Moreover, a comparison between the experimental and theoretical FT-IR spectra was shown in Figure 2. Since nonharmonic effects are ignored in the theoretical process, the measured quantum chemical harmonic vibrational frequencies are usually greater than the fundamentals found experimentally [29][30][31]. In the current study, a scale factor of 0.9978 [32] was used to compare the experimental vibrational modes with the theoretical frequencies for the 4-AHT molecule.…”

Section: Assignment Of Vibrational Spectramentioning

confidence: 98%

Investigations on spectroscopic characterizations, molecular docking, NBO, drug-Likeness, and ADME properties of 4H-1,2,4-triazol-4-amine by combined computational approach

Celik

Yurdakul

2021

Eur J Chem

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In this study, the spectroscopic characterization, frontier molecular orbital analysis, and natural bond orbital analysis (NBO) analysis were executed to determine the movement of electrons within the molecule and the stability, and charge delocalization of the 4H-1,2,4-triazol-4-amine (4-AHT) through density functional theory (DFT) approach and B3LYP/6-311++G(d,p) level of theory. Surface plots of the hybrids’ Molecular Electrostatic Potential (MEP) revealed probable electrophilic and nucleophilic attacking sites. The discussed ligand were observed to be characterized by various spectral studies (FT-IR, UV-Vis). The calculated IR was found to be correlated with experimental values. The UV-Vis data of the molecule was used to analyze the visible absorption maximum (λmax) using the time-dependent DFT method. Since the principle of drug-likeness is usually used in combinatorial chemistry to minimize depletion in pharmacological investigations and growth, drug-likeness and ADME properties were calculated in this research to establish 4-AHT molecule bioavailability. Furthermore, molecular docking studies were carried out. Molecular docking analysis was performed for the title ligand inside the active site of the Epidermal Growth Factor Receptor (EGFR). The title compound’s anti-tumor activity against the cancer cell, in which EGFR is strongly expressed, prompted us to conduct molecular docking into the ATP binding site of EGFR to predict whether this molecule has an analogous binding mode to the EGFR inhibitors (PDB: ID: 1M17).

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A combined experimental and theoretical approach for structural, spectroscopic, NLO, NBO, thermal and photophysical studies of new fluorescent 5-amino-1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazole-4-carbonitrile using density functional theory

Cited by 13 publications

References 69 publications

A Mixed Heavier Si=Ge Analogue of a Vinyl Anion

A Mixed Heavier Si=Ge Analogue of a Vinyl Anion

Ein gemischtes, schwereres Si=Ge Analogon eines Vinylanions

Investigations on spectroscopic characterizations, molecular docking, NBO, drug-Likeness, and ADME properties of 4H-1,2,4-triazol-4-amine by combined computational approach

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