Calculation of the vibrational spectrum of rhodanine dimer structures

Yakimenko, V. I.; Lebedev, R. S.

doi:10.1007/bf00890481

Soviet Physics Journal

1973

DOI: 10.1007/bf00890481

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Calculation of the vibrational spectrum of rhodanine dimer structures

V. I. Yakimenko¹,

R. S. Lebedev²

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2012

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“…However, there is no experimental proof for the existence of type 2b dimers. Dimer 2d also is similar in energy to dimers 2a and 2b; Yakimenko and Lebedev [33] have even calculated the vibrational spectra of this dimer and compared them with the vibrational spectra of dimer 2a. Dimer 2c attracts interest due to its type of intermolecular interaction.…”

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Theoretical study of the dimerization of rhodanine in various tautomeric forms

Baryshnikov

Минаев

Минаева

et al. 2012

Chem Heterocycl Comp

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The density functional theory (DFT) was used to calculate the relative stability of rhodanine dimers and the energy of intermolecular interaction in them. Analysis of the electron density showed hydrogen bonding in the dimers. The energies of individual hydrogen bonds were determined for the symmetrical dimers. The polarizable continuum model was used to calculate the solvation (hydration) energies of the structures studied. The effect of dimerization on the position of infrared absorption bands was demonstrated.Rhodanine (2-thioxothiazolidin-4-one) and its derivatives, which are common reagents in analytical and coordination chemistry, attract special interest in medicine, biochemistry, and photochemistry. Rhodanine derivatives modified at the methylene group (ylidenerhodanines) possess antibacterial [1], antifungal [2-4], antidiabetic [5], and anticancer activity [6]. This accounts for the use of rhodanine in the pharmaceutical industry [5].Free rhodanine is used for the synthesis of indoline, triphenylamine, and phenothiazine sensitizing dyes for solar cells [7]. The rhodanine group in dye compositions acts as an electron density acceptor. Rhodanine also forms strong colored coordination compounds with many heavy metal ions such as Pd 2+ , Pt 2+ [8], Ag + , Au + [9], Cu + [10], Ni 2+ , Co 2+ [11], Cu 2+ , Hg 2+ , Au 3+ , and Ru 3+ [12] what is used for their spectrophotometric determination.Rhodanine may exist in ketone, enol, and thioenol tautomeric forms [13][14][15][16][17] due to the presence of ketone and thioketone functional groups in a molecule and an active hydrogen atom of the NH bond (with dissociation constant K d = 10 -8 in water [13,14]). The enol and thioenol tautomers can each form two rotamers, while a total of eleven tautomers and rotamers exist taking account of the possible dissociation of rhodanine at the methylene group CH bond [17]. Thus, we might expect the existence of a wide variety of dimeric complexes, which may be formed in crystals, solutions, and the gas phase.Loncharich et al. [13] have carried out an X-ray diffraction structural analysis and experimentally identified some of the dimers predicted in our earlier work. This offered the prospect of identifying other dimeric complexes.In the present work, we present the results of quantum-chemical modelling for various rhodanine dimers. These data contribute to a general understanding of the dimerization behavior and may be useful for developing the chemistry of rhodanines and ylidenerhodanines as well as for methods of infrared spectral

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confidence: 94%

Theoretical study of the dimerization of rhodanine in various tautomeric forms

Baryshnikov

Минаев

Минаева

et al. 2012

Chem Heterocycl Comp

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Calculation of the vibrational spectrum of rhodanine dimer structures

Cited by 1 publication

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Theoretical study of the dimerization of rhodanine in various tautomeric forms

Theoretical study of the dimerization of rhodanine in various tautomeric forms

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