Studies on molecular structure and tautomerism of a vitamin B6 analog with density functional theory

Sahoo, Suban K.; Sharma, Darshna; Bera, Rati Kanta

doi:10.1007/s00894-011-1214-1

Cited by 13 publications

(5 citation statements)

References 40 publications

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“…Related systems. Six-member rings with an intramolecular H-bond have been found for a number of systems such as 2-phenyliminomethyl-naphthalen-l-ol [ 235 , 236 ], its isomer, 1-phenyliminomethyl-naphthalen-2-ol, and substituted 3-hydroxy-4-pyridaldehyde deivatives [ 237 ]. For these molecules, the covalent structure assures the possibility of the intramolecular hydrogen bond in some preferable conformation.…”

Section: Conformational Equilibriamentioning

confidence: 99%

Competing Intramolecular vs. Intermolecular Hydrogen Bonds in Solution

Nagy

2014

IJMS

145

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A hydrogen bond for a local-minimum-energy structure can be identified according to the definition of the International Union of Pure and Applied Chemistry (IUPAC recommendation 2011) or by finding a special bond critical point on the density map of the structure in the framework of the atoms-in-molecules theory. Nonetheless, a given structural conformation may be simply favored by electrostatic interactions. The present review surveys the in-solution competition of the conformations with intramolecular vs. intermolecular hydrogen bonds for different types of small organic molecules. In their most stable gas-phase structure, an intramolecular hydrogen bond is possible. In a protic solution, the intramolecular hydrogen bond may disrupt in favor of two solute-solvent intermolecular hydrogen bonds. The balance of the increased internal energy and the stabilizing effect of the solute-solvent interactions regulates the new conformer composition in the liquid phase. The review additionally considers the solvent effects on the stability of simple dimeric systems as revealed from molecular dynamics simulations or on the basis of the calculated potential of mean force curves. Finally, studies of the solvent effects on the type of the intermolecular hydrogen bond (neutral or ionic) in acid-base complexes have been surveyed.

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Section: Conformational Equilibriamentioning

confidence: 99%

Competing Intramolecular vs. Intermolecular Hydrogen Bonds in Solution

Nagy

2014

IJMS

145

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“…In contrast, the experimental values belong to the solid phase determined by X-ray diffraction. As shown in Figure 2 and Figure 3 , the existence of intermolecular interactions in the solid phase, such as van der Waals interactions, hydrogen bonding, π···π and CH···π interactions, etc., resulted in the difference of bond parameters between the experimental and the calculated values [ 47 ]. Furthermore, to account for the accuracy of the theoretical approach, the DFT computed structures of 1 and 2 were superimposed with those obtained from X-ray crystallography, giving a root-mean-square error (RMSE) of 0.190 Å and 0.155 Å, respectively ( Figure 4 ).…”

Section: Resultsmentioning

confidence: 99%

Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative

et al. 2022

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The hydrazine derivatives are known to possess several biological activities including anticancer, antibacterial and anti-fungal, anticonvulsant, and antioxidant. This communication presents the synthesis, X-ray crystal structure analysis, DFT calculations, cell cytotoxicity, and antioxidant activity of the Schiff base 4,4′-((1E,1′E)-hydrazine-1,2-diylidenebis(ethan-1-yl-1-ylidene))bis(benzene-1,3-diol) (compound 2). We have also isolated the side product compound 1 and characterized it using single X-ray crystallography. The crystal structure of compound 1 depicts that the ensuing C‒H···N hydrogen bonding interaction is presented and discussed herein. In addition, the calculations using density functional theory (DFT) approximation supported by experimental 1H and 13C NMR studies on the key compound 2 are reported. The results of theoretical and experimental 1H and 13C NMR were concordant. The antioxidant activity of compound 2 was determined by using 2,2′-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS•+) radical cation assays and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical assay. Compound 2 demonstrated excellent antioxidant activity in ABTS assay (IC50 = 4.30 ± 0.21 µM) and DPPH assay (IC50 = 81.06 ± 0.72 µM) with almost no cytotoxicity below 25 µM.

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“…Receptor L was synthesized by following the reported method [36][37][38], and its sensing ability was tested towards various metal ions. (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

Cation Sensing of Pyridoxal Derived Sensors Towards Fe (II) Ion in Pure Aqueous Solution.

Rana¹,

Rana²,

Sahoo³

2017

Chem Sci J

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A novel sensor (L) was synthesized using Schiff base reaction of pyridoxal with orthophenylene diamine and was characterized by various spectroscopic techniques such as FTIR, 1 H NMR and Mass spectrometry. The cation recognition ability of the synthesized sensor was investigated by experimental (UV-VIS, IR and 1 H NMR) and theoretical (B3LYP/6-31G**) methods. Among the tested anions, the developed sensor showed a naked-eye detectable color change from colorless to yellow and spectral changes in the presence of Fe(II) due to the formation of hydrogen bonded complexes with these cations followed by the partial deprotonation of sensor. With a micromolar detection limit, the developed sensor proved highly efficient and can be utilized for the colorimetric detection of Fe(II) ions.

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Studies on molecular structure and tautomerism of a vitamin B6 analog with density functional theory

Cited by 13 publications

References 40 publications

Competing Intramolecular vs. Intermolecular Hydrogen Bonds in Solution

Competing Intramolecular vs. Intermolecular Hydrogen Bonds in Solution

Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative

Cation Sensing of Pyridoxal Derived Sensors Towards Fe (II) Ion in Pure Aqueous Solution.

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