Density functional theory study on the ionic liquid pyridinium hydrogen sulfate

Tankov, Ivaylo; Yankova, Rumyana; Genieva, Svetlana; Mitkova, Magdalena; Stratiev, Dicho

doi:10.1016/j.molstruc.2017.03.040

Cited by 60 publications

(32 citation statements)

References 40 publications

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“…The highest yield of methylbenzoate ester was obtained with [PyH][HSO 4 ], 1a under the optimized conditions (Table , entry 1). The similar activity of Brønsted ionic liquids with HSO 4 − anion has also been reported in other instances of the Fischer esterification reaction . On the other hand, the pyridinium containing citrate and NO 3 − anions demonstrated poor activity.…”

Section: Catalytic Studysupporting

confidence: 80%

“…Synthesized ionic liquids were characterized by the 1 H NMR, IR spectroscopy, and high resolution‐mass spectrometry (HRMS). The presence of a broad resonance signal at δ H 13.01 ( 1a ), 15.59 ( 1b ), 13.0 ( 1c ), 10.96 ( 1d ), 14.9 ( 1e ), 9.40 ( 2a ), 9.05 ( 2b ), 9.28 ( 2c ), 9.00 ( 2d ), and 8.94 ( 2e ) ppm in the 1 H NMR spectrum confirms the formation of N−H bond (Supporting Information) . It is further supported by IR spectroscopy which exhibits a broad absorption band at 2990–3035 cm −1 attributed to N−H bond stretching vibrations…”

Section: Resultssupporting

confidence: 55%

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Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions

Bano

Jain²,

Sarkar

et al. 2020

ChemistrySelect

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Brønsted acidic ionic liquids (BAILs) have been used as catalyst and solvent in organic synthesis, due to their negligible volatility, remarkable solubility, good catalytic activity, and easily structurally tunable properties. In the present study, we have investigated the catalytic efficiency of economically viable ionic liquids bearing different cations pyridinium ([PyH] + and triethylammonium [TEAH] + ) for the esterification of aromatic acid with various aliphatic alcohols and crossed aldol condensation of aromatic aldehydes with cyclohexanone under ambient condition. We also examined the effect of various process parameters on the yield of aromatic esters and α,α'-bis (arylidene)cycloalkanones.

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Section: Catalytic Studysupporting

confidence: 80%

Section: Resultssupporting

confidence: 55%

Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions

Bano

Jain²,

Sarkar

et al. 2020

ChemistrySelect

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“…33 The FMOs and their negative (green) and positive (red) regions obtained by the B3LYP method with 6-311++G(2d,2p) basis set for the S-(+)-carvone are shown in Figure 3(a η are an indication for the polarizability and reactivity of a given compound. [35][36][37][38][39] Calculations show that the values of 2.2583 and 0.387 eV characterize η and S , respectively, in the case of S-(+)-carvone. Therefore, the title compound was denoted as a highly polarizable and reactive material.…”

Section: Electronic Properties and Chemical Reactivitymentioning

confidence: 99%

Electronic structure, reactivity, and Hirshfeld surface analysis of carvone

Yankova

Dimov

Dobreva

et al. 2019

Journal of Chemical Research

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The density functional theory (at the B3LYP level using 6-311++G(2d,2p) basis set) was used for the investigation of the geometry and electronic properties of the carvone. The electronic properties and chemical activity of the titled compound were investigated by means of several theoretical approaches, molecular electrostatic potential surface, natural bond orbital, and frontier molecular orbital analyses. It was established that the oxygen atom in the structure characterized the electrophilic reactivity; the positive regions are localized on the hydrogen atoms, which can be considered as possible sites for nucleophilic attack. A detailed analysis of the intermolecular interactions via Hirshfeld surface analysis and fingerprint plots revealed that the carvone structure is stabilized mainly by the formation of O. . .H/H. . .O hydrogen bonds. However, close contacts were established between C. . .H/H. . .C and H. . .H contacts.

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“…The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) is quite important in quantum chemistry as they allow the investigation of stability and reactivity of molecules [ 26 ]. However, in a typical system, the HOMO acts as an electron donor, and the LUMO primarily acts as the electron acceptor [ 26 , 30 , 31 ]. The total energies of HOMO-LUMO and other descriptors of the investigated mycotoxins were calculated using the B3LYP/6-31+G(d,p) level.…”

Section: Resultsmentioning

confidence: 99%

“…Sub-shells as seen in Table S6. The NBO analysis of the investigated mycotoxins is carried out to predict the delocalization patterns of electron density from the principal occupied Lewis-type orbitals to unoccupied non-Lewis-type orbitals (from the bonding orbitals to anti-bonding orbitals) [ 31 , 41 , 42 ].…”

Section: Resultsmentioning

confidence: 99%

Investigation on electronic structure, vibrational spectra, NBO analysis, and molecular docking studies of aflatoxins and selected emerging mycotoxins against wild-type androgen receptor

Agwupuye

Neji

Louis

et al. 2021

Heliyon

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The geometry, frontier molecular orbitals (FMOs), vibrational, NBO analysis, and molecular docking simulations of aflatoxins (B1, B2, M1, M2, G1, G2), zearalenone (ZEA) emodin (EMO), alternariol (AOH), alternariol monoethyl ether (AMME), and tenuazonic acid (TeA) mycotoxins have been extensively theoretically studied and discussed based on quantum density functional theory calculations using Gaussian 16 software package. The theoretical computation for the geometry optimization, NBOs, and the molecular docking interaction was conducted using Density Functional Theory with B3LYP/6-31+G(d,p), NBO program, and AutoDock Vina tools respectively. Charge delocalization patterns and second-order perturbation energies of the most interacting natural bond orbitals (NBOs) of these mycotoxins have also been computed and predicted. Interestingly, among the mycotoxins investigated, aflatoxin G1 is seen to give the strongest stabilization energy while Zearalenone shows the highest tendency to accept electron(s) and emodin, an emerging mycotoxin gave the best binding pose within the androgen receptor pocket with a mean binding affinity of -7.40 kcal/mol.

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Density functional theory study on the ionic liquid pyridinium hydrogen sulfate

Cited by 60 publications

References 40 publications

Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions

Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions

Electronic structure, reactivity, and Hirshfeld surface analysis of carvone

Investigation on electronic structure, vibrational spectra, NBO analysis, and molecular docking studies of aflatoxins and selected emerging mycotoxins against wild-type androgen receptor

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