Synthesis, structure, and properties of phosphorus-containing bis(amidrazones)

Попов, Л. Д.; Shcherbakov, I. N.; Tkachenko, Yu. N.; Бородкин, С. А.; Коган, В. А.

doi:10.1134/s107036320608007x

Cited by 5 publications

(3 citation statements)

References 14 publications

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“…Then, important molecular parameters, IR frequencies, and energetic results were extracted. The relative stabilities of amidrazone isomers in the gas phase are found to be as 1Z (1)(2) [ TS (1)(2)(3). Energetic data confirm that its major tautomer is 1 and all possible tautomerism interconversions have very small rate at room Negative values refer to unstabilizing effect and positive values refers to the stabilizing effects, please pay attention that the energy barriers (Table 7) were calculated versus 1Z tautomers (the most stable tautomer) while the above data refer to the 1E tautomers temperature.…”

Section: Resultsmentioning

confidence: 98%

“…For example, their structures [3], complexation properties [10], and IR frequencies [25] were reported in the literature. Another interesting aspect of amidrazones is tautomerism.…”

Section: Introductionmentioning

confidence: 98%

“…Amidrazones [1][2][3] (amide hydrazones or hydrazide imides) are the subject of interest because of their biological activities [5][6][7][8][9] and their capacity in formation of complexes [4]. The preparation of amidrazones was reported by different methods such as addition of sodium hydrazide to nitriles [10], reaction of nitrohydrazones with amines [11], and enzymatic methodologies [12].…”

Section: Introductionmentioning

confidence: 99%

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DFT and MP2 study of simple and water-assisted tautomerism in amidrazones

Tavakol

2011

Struct Chem

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DFT and MP2 methods were used to calculate structural parameters, vibrational modes, solvent effect, and energetic properties of amidrazones. Amidrazones can be presented by three tautomeric forms and six isomers. All tautomers and transition states were optimized at the B3LYP/6-311??g** and MP2/6-311??G** levels of theory. The relative stabilities of amidrazone isomers in the gas phase were found to be as 1Z. The calculated energy differences between E and Z isomers are very low and between different tautomers are nearly low, but the energy barriers for tautomerism interconversions at the gas phase are high. The kinetic and thermodynamic data in solvents (chloroform, tetrahydrofuran, acetone, and water) are nearly similar to those in the gas phase but their rate constants are slightly less than those in the gas phase. Moreover, equilibrium and rate constants of intermolecular tautomerism in presence of 1-3 molecules of water were calculated. Computed energy barriers show that the barrier energy of water-assisted tautomerism is very lower than that in simple tautomerism and also calculated binding energies show that water can stabilize transition states more than tautomers. Therefore, this water-assisted tautomerism can be performed fast, especially with the assistance of two molecules of water.

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Section: Resultsmentioning

confidence: 98%

“…For example, their structures [3], complexation properties [10], and IR frequencies [25] were reported in the literature. Another interesting aspect of amidrazones is tautomerism.…”

Section: Introductionmentioning

confidence: 98%