Experimental and DFT evaluation of the 1H and 13C NMR chemical shifts for calix[4]arenes

Guzzo, Rodrigo N.; Rezende, Michelle J. C.; Kartnaller, Vinicius; Carneiro, José Walkimar de M.; Stoyanov, Stanislav R.; Costa, Leonardo Moreira da

doi:10.1016/j.molstruc.2017.12.038

Cited by 11 publications

(3 citation statements)

References 48 publications

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“…Correlation results through linear regression analysis showed the value of R 2 and R 0 2 ≥ 90% (Table 2), with the linear equations for each compound found to be y = 0.8817x + 0.7945 (in gas) and y = 0.9011x + 0.8112 (in acetone) for DS1 and y = 1.1594x - between experimental and theoretical is presented by the MAE, RMSE, and MAPE parameters, as detailed in Table 2. Commonly, the smaller the parameter value, the better the accuracy results, [49] and particularly for the MAPE parameter, our results showed that each model has a MAPE ≤ 10%.…”

Section: Proton Chemical Shiftmentioning

confidence: 70%

Pharmacokinetic, DFT Modeling, Molecular Docking, and Molecular Dynamics Simulation Approaches: Diptoindonesin A as a Potential Inhibitor of Sirtuin-1

Abdjan¹,

Aminah²,

Kristanti³

et al. 2022

Eng. Sci.

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Sirtuin 1 (SIRT1) is a class III histone deacetylase that regulates several cellular processes. SIRT1 overexpression is found in many cancer cases and is a potential therapeutic target. Unlike resveratrol, several stilbenoid dimers have been identified as SIRT1 inhibitors. This work studied the interaction and dynamic behavior of stilbenoid dimers and SIRT1. Prediction of binding free energy (∆Gbind) was calculated using the QM/MM-GBSA approach for each system, which resulted in 1NS-SIRT1: -21.44 kcal/mol, DS1-SIRT1: -25.94 kcal/mol, and DS2-SIRT1: -12.48 kcal/mol. These indicated that DS1 has a better chance as a SIRT1 inhibitor than DS2. The presence of glucose groups in DS1 potentially increased intermolecular interactions in the form of key residues and hydrogen bonds. Additionally, the quantum mechanical properties of DS1 and DS2 using the DFT/B3LYP/6-311++G(d,p) method were applied. The DS1 has three hydroxyls in the glucose group (3'-OH, 4'-OH, and 6'-OH) that could be reactive as nucleophiles and electrophiles. Furthermore, pharmacokinetic studies showcased the non-toxic properties of DS1.The analyses presented in this study could provide information on the quantum mechanical properties and inhibitory efficiency of stilbenoid dimers based on computational studies.

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Section: Proton Chemical Shiftmentioning

confidence: 70%

Pharmacokinetic, DFT Modeling, Molecular Docking, and Molecular Dynamics Simulation Approaches: Diptoindonesin A as a Potential Inhibitor of Sirtuin-1

Abdjan¹,

Aminah²,

Kristanti³

et al. 2022

Eng. Sci.

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“…Notably, the resonance arising from the bridging methylene groups is an important characteristic of the 1 H NMR spectra of calixarenes . Singlet resonances appear within the 1 H NMR spectrum because of proton resonances of tert -butyl, Ar–H, and O–H groups . The variation of the O–H singlet position is attributed to the change in ring size of the calixarene skeleton because of complexation …”

Section: Resultsmentioning

confidence: 99%

“…62 Singlet resonances appear within the 1 H NMR spectrum because of proton resonances of tert-butyl, Ar−H, and O−H groups. 74 The variation of the O−H singlet position is attributed to the change in ring size of the calixarene skeleton because of complexation. 66 On complexation, all proton chemical shifts experienced different degrees of variation.…”

Section: Energy and Fuelsmentioning

confidence: 99%

Novel (Co-,Ni)-p-tert-Butylcalix[4]arenes as Dispersed Catalysts for Heavy Oil Upgrading: Synthesis, Characterization, and Performance Evaluation

Al‐Attas¹,

Zahir²,

Ali³

et al. 2018

Energy Fuels

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This study investigates the promotional effects of a potentially new class of oil-soluble dispersed catalyst precursors for upgrading of vacuum gas oil (VGO), that is metal-based p-tert-butylcalix[4]arenes (TBC[4]s). Co- and Ni-TBC[4] were synthesized, and the metal–ligand complexation was confirmed by scanning electron microscopy-energy dispersive X-ray, inductively coupled plasma, X-ray diffraction, UV–vis, Fourier transform infrared, and 1H NMR. The thermogravimetric and calorimetric behaviors of the synthesized complexes, which are key properties of dispersed hydrocracking catalysts, were also studied. The differential scanning calorimetry profile of Ni-TBC[4] and Co-TBC[4] showed that the organometallic structure has lower thermal stability compared with that of the parent TBC[4]. This apparent drawback can be positively exploited by employing TBC[4] as a carrier of the metal, where the active sites are formed in situ by the destruction of the organometallic complex on reaching the desired reaction conditions. The catalytic performance of the synthesized precursors was evaluated using a batch autoclave reactor with varying concentrations of catalyst precursors at 420–450 °C. The results show that the synthesized metal-based TBC[4] dispersed catalysts evidently enhanced the hydrogenation activity and reduced coke formation. The addition of 500 ppm Co and Ni as standalone dispersed catalysts produced distillate yields of 45.7 and 49.7 wt % and a coke laydown of 2.6 and 2.3 wt %, respectively. Increasing the concentration of catalyst precursors enhanced the conversion of VGO from 86.17% at 100 ppm Ni to 88.28% at 500 ppm Ni. Moreover, as the metal concentration increased from 100 to 500 ppm, the distillate yield increased from 36.87 to 49.66 wt %, while the yield of gases decreased from 20.48 to 17.12 wt % because the hydrogenation reactions were enhanced. In contrast, the yields of distillate and naphtha decreased by 14.12 and 15.36%, respectively, as the temperature increased from 420 to 450 °C.

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Role of hydrogen bonding interactions within of the conformational preferences of calix[n = 4,6,8]arene: DFT and QTAIM analysis

et al. 2019

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Experimental and DFT evaluation of the 1H and 13C NMR chemical shifts for calix[4]arenes

Cited by 11 publications

References 48 publications

Pharmacokinetic, DFT Modeling, Molecular Docking, and Molecular Dynamics Simulation Approaches: Diptoindonesin A as a Potential Inhibitor of Sirtuin-1

Pharmacokinetic, DFT Modeling, Molecular Docking, and Molecular Dynamics Simulation Approaches: Diptoindonesin A as a Potential Inhibitor of Sirtuin-1

Novel (Co-,Ni)-p-tert-Butylcalix[4]arenes as Dispersed Catalysts for Heavy Oil Upgrading: Synthesis, Characterization, and Performance Evaluation

Role of hydrogen bonding interactions within of the conformational preferences of calix[n = 4,6,8]arene: DFT and QTAIM analysis

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