The electronic and spectroscopic investigation of (±)- Dasycarpidone

Serdaroğlu, Goncagül; Uludag, Nesimi

doi:10.1016/j.vibspec.2020.103156

Cited by 25 publications

(14 citation statements)

References 45 publications

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“…Due to the mainly sp 2 Here, the calculated NMR shifts were calculated greater than the relevant recorded data, as expected from the literature. [74][75] Results obtained from the NMR study give further support to the binding mode discussed in IR spectra.…”

Section: Nmr Spectral Studysupporting

confidence: 56%

“…The band observed at 3135 cm À 1 was assigned as NÀ H elongation mode at 3422 cm À 1 . Recently, the υNH elongation band for primary and secondary amines was observed in ∼ 3500-3300 cm À 1 , [76] and reported by theoretical calculations at 3300-3500 cm À 1 , [73][74][75]77] respectively. Also, υN=C vibrations for the azomethine and thiazole ring of compound 3 were assigned at 1618, 1598, 1213 cm À 1 , and 1495 and 1440 cm À 1 , respectively.…”

Section: Ft-ir Spectral Studymentioning

confidence: 88%

“…NBO method provides essential information of the molecular systems considering the intra-molecular interactions such as resonance, hyperconjugative, anomeric, etc. In this context, there have been reported [72][73][74][75][85][86][87][88] a lot of works from the simple-organic systems to complex molecules that evaluated the chemical stability, reactivity, and polarizability via using the NBOs approaches and the second-order perturbative energy analysis.…”

Section: Nbo Studymentioning

confidence: 99%

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New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

Erdoğan

Serdaroğlu

2021

ChemistrySelect

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A novel pyrene-sulfathiazole-based potential drug candidate 3 was designed, successfully synthesized by a condensation reaction of pyrenecarboxaldehyde (1) with sulfathiazole (2) in good yield, and fully characterized by NMR, IR, UV-Vis, and HRMS spectroscopic techniques. The TD-DFT/B3LYP calculations displayed that the recorded peaks at 396, 377, 280, and 236 nm were due to the mainly n-π* and partially π-π* transitions that occurred on pyrene, azomethine, and sulfathiazole moieties. The NBO results disclosed that the electron delocalizations happened onto sulfathiazole, aromatic rings (pyrene and Ph-), and azomethine groups had the main responsibility of the lowering stabilization energy of compound 3. The NMR shifts were calculated by using the GIAO approaches in the DMSO phase and compared with the relevant data recorded. The thermodynamic and quantum chemical quantities were used for elucidating the physicochemical properties and reactivity behavior, in THF, DMSO, and water simulation environments. Accordingly, the calculated DM (D) and α (au) order of compound 3 were calculated in the order of vacuum < THF < DMSO < water, which indicated that the stability and thus reactivity of the compound strongly depended on the solvent environment. The FMO studies implied that the electron-donating possibility of compound 3 was dominant to the electron-accepting potency. In this work, the SMD version of IEFPCM was used in solvent media simulations.

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Section: Nmr Spectral Studysupporting

confidence: 56%

Section: Ft-ir Spectral Studymentioning

confidence: 88%

Section: Nbo Studymentioning

confidence: 99%

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New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

Erdoğan

Serdaroğlu

2021

ChemistrySelect

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“…NBO analysis is performed for molecular systems to provide very useful clues regarding their electronic structure in terms of predicting both intramolecular and intermolecular interactions, and therefore evaluating possible electrophilic or nucleophilic attack sites. 25–27,111 For all the compounds, the greatest contribution to the lowering of energy is due to the electron movement from the lone pair of nitrogen to the π* C6–C7 and π* C13–O14 antibonding orbitals (Table S4, ESI†). The LP (1) N11→ π* C6–C7 and LP (1) N11→ π* C13–O14 interactions for compound C1 were calculated with the energies of 38.32 and 45.93 kcal mol −1 , respectively.…”

Section: Resultsmentioning

confidence: 99%

A novel series of tetrahydrothieno[2,3-c]pyridin-2-yl derivatives: fluorescence spectroscopy and BSA binding, ADMET properties, molecular docking, and DFT studies

et al. 2023

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“…[27] The chemical shifts related to sp 3 hybridized Cs were recorded in 25.0-56.4 ppm and were computed in the rank of 27.6-59.7 ppm by B3LYP level. [51] Furthermore, the highest shifts for all pyrroles have been recorded for the proton of the À NH group. Namely, the apparent peak at 10.33 ppm of the 1H NMR spectrum for Ph-F has been assigned at 8.83 ppm, whereas the corresponding peak for Ph-tBC has been recorded at 9.97 and calculated at 8.87 ppm.…”

Section: Nmr and 1 H Nmr Spectramentioning

confidence: 94%

Advancing Pyrrole Synthesis through DDQ Catalysis: A Comprehensive Research Incorporating DFT, ADMT, and Molecular Docking Analysis

Serdaroğlu,

Uludağ,

Üstün

2024

ChemistrySelect

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The construction of pyrroles is an important heterocyclic group comprising many compounds with interesting properties that have led to numerous applications in various fields. We delineate a new synthetic method for the rapid construction of tree‐substituted pyrroles from readily available ketoximes as starting materials and also a new mechanism and method has been proposed. It is presented that substituted pyrroles were efficiently synthesized in high yields (up to 81 % yield) through the cyclization reaction of starting ketoximes mediated by 2,3‐dichlor‐5,6‐dicyanobenzoquinone (DDQ). Utilizing this protocol various pyrrole derivatives were synthesized from diethyl acetylene dicarboxylate (DEAD). We then developed the dehydrogenation reaction mechanism of this formation, also studied in detail, also all synthesized compounds were analyzed in detail by spectroscopic techniques (FT‐IR, 1H NMR, 13CNMR) which were compared with the computational data estimated at B3LYP/6‐311G** level. The thermochemical and electronic properties of the pyrroles were evaluated after optimizing and then confirming the equilibrium structures. ADMT scores were also considered to estimate/elucidate the possible bioavailability tendencies as well as the toxicity. In addition, the interactions of the optimized molecules were evaluated by molecular docking methods against BSA “Bovine Serum Albumin” and LIF “Leukemia Inhibitory Factor”. The results obtained from this study will ideally provide a fundamental source in contemporary drug design in terms of both the key electronic properties underlying the possible reactivity features and toxicity.

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The electronic and spectroscopic investigation of (±)- Dasycarpidone

Cited by 25 publications

References 45 publications

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

A novel series of tetrahydrothieno[2,3-c]pyridin-2-yl derivatives: fluorescence spectroscopy and BSA binding, ADMET properties, molecular docking, and DFT studies

Advancing Pyrrole Synthesis through DDQ Catalysis: A Comprehensive Research Incorporating DFT, ADMT, and Molecular Docking Analysis

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