Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties

Teuber, Lene

doi:10.1080/01961779008048732

Cited by 36 publications

(18 citation statements)

References 336 publications

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“…Considering the geometrical dimension of the five-membered ring it can be seen that the two C-Se bond lengths [1.971 (2) An interesting correlation between a decrease of the torsion angle around the disulfide bridge and an increase of the S-S bond length has been reported by Bock et al [21] It is now well established that the major contribution to the enhanced reactivity of 1,2-dithiolanes arises from the small dihedral angle around the S-S bond associated with the reduced size of the ring and by the resulting unfavorable interaction between the adjacent sulfur lone pairs. [22] Accordingly, the S-S bond in 1,2-dithiolanes is longer and weaker than that found in open-chain disulfides, whose dihedral angle is close to 90°. Similar geometrical peculiarities are also characteristic for the related compound 4d, in which the dihedral angle around the diselenide bridge is 0.57(7)°a nd the Se-Se bond length [2.3580(3) Å] is longer than that in strain-free, open-chain diselenides (2.340 Å).…”

Section: Resultsmentioning

confidence: 98%

Catalyst Leaching as an Efficient Tool for Constructing New Catalytic Reactions: Application to the Synthesis of Cyclic Vinyl Sulfides and Vinyl Selenides

et al. 2009

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Catalyst leaching from Pd and Ni particles stabilized by organic sulfur and selenium ligands occurs in solution in the presence of phosphanes. This process has been monitored in real time by 1D and 2D NMR spectroscopy and the nature of the metal species established. This catalyst leaching is shown to be a powerful tool for generating new catalytic activity from species formed in situ where the parent bulk particles

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Section: Resultsmentioning

confidence: 98%

Catalyst Leaching as an Efficient Tool for Constructing New Catalytic Reactions: Application to the Synthesis of Cyclic Vinyl Sulfides and Vinyl Selenides

et al. 2009

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“…There are many naturally‐occurring cyclic disulfides 35 and they can be seen as sustainable building blocks of (bio)degradable materials. Among them, lipoic acid (LpOH), 36,37 which plays a number of important biological roles, for example, in metabolism, 38 is the best known and perhaps the most attractive because it is readily available and is essentially nontoxic.…”

Section: Introductionmentioning

confidence: 99%

Radical ring‐opening polymerization of lipoates: Kinetic and thermodynamic aspects

Raeisi

Tsarevsky

2021

Journal of Polymer Science

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The radical ring‐opening polymerization of a lipoate‐based monomer, ethyl lipoate, in bulk and in solution was studied at various temperatures and it was found that in all cases, only limited (plateau) conversions were reached, which were lower at higher temperatures and/or at higher dilutions. It was established that a monomer‐polymer equilibrium exists with a corresponding ceiling temperature of 139°C. Due to the reversibility of the lipoate polymerization, when poly(ethyl lipoate) was heated to 150°C, it degraded and within 3 h, the molecular weight decreased to less than 15% of the initial value. Likewise, when the polymer was dissolved in anisole and a radical initiator was added, degradation was observed even at 60°C and it became increasingly pronounced at higher concentrations of the radical source. Due to the presence of multiple disulfide groups in the backbone, poly(ethyl lipoate) also degraded in the presence of reducing agents, such as tributylphosphine, yielding the reduced (dithiol) form of the monomer, ethyl dihydrolipoate.

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“…Among the various of anthraquinones are identified also biologically active compounds. A lot of anthraquinone compounds are found in plants, microorganisms [13], among of them are natural antibiotics anthracyclines [14] and cidamicines [15]. Recently, anthracene derivatives actively began to gain new application areas such as biologically active agents, analytical reagents [16][17][18], phosphors [19], the components of liquid crystal compositions, photo materials, chemical additives for polymeric materials and they have found their application in color photography and electrophotography, laser technology, LCD and photochromic materials [20,21].…”

Section: Introductionmentioning

confidence: 99%

TD-DFT Calculations, NBO, NLO Analysis and Electronic Absorption Spectra of Some Novel Thiazolo[3,2-a]Pyridine Derivatives Bearing Anthracenyl Moiety

Hussien¹

2019

IJCTC

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The electronic structure and spectra of the studied compounds 1-4 are investigated using TD-DFT/B3LYB/6-311G (d, p) level of theory. The results of calculations show that all the studied compounds 1-4 are non-planar, as indicated from the dihedral angles. The electronic absorption spectra of the studied compounds are recorded in the UV-VIS region, in both Acetone (as polar solvent) and Xylene (as non-polar solvent). The observed vertical electronic transitions assignments are facilitated via time-dependent density functional theory TD-DFT. Solvent dependence of the band maxima (λ max ) and intensities of the observed spectra are explained in terms of blue and red shifts. Electronic configurations contributing to each excited state are identified and the relevant MOs are characterized. The natural bond orbital (NBO) analysis were discussed in terms of the extent of delocalization, intermolecular charge transfer and second order perturbation interactions between donor and acceptor MOs. The Coulomb-attenuating method (CAM-B3LYP) and Corrected Linear Response Polarizable Continuum Model (CLR) PCM studied for theoretically obtaining the electronic absorption spectra in gas phase, Acetone and Xylene, respectively, indicate a good agreement with the observed spectra. The calculated nonlinear optical parameters (NLO); polarizibilty (α), anisotropy of the polarizibility (∆α) and first order hyperpolarizibility (β) of the studied compounds show promising optical properties. The HOMO-LUMO energy gap helped in analyzing the chemical reactivity, hardness, softness, chemical potential and electro negativity. 3D-plots of the molecular electrostatic potential (MEP) for the studied compounds are investigated and analyzed showing the distribution of electronic density of orbital's describing the electrophilic and nucleophilic sites of the selected molecules.

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Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties

Cited by 36 publications

References 336 publications

Catalyst Leaching as an Efficient Tool for Constructing New Catalytic Reactions: Application to the Synthesis of Cyclic Vinyl Sulfides and Vinyl Selenides

Catalyst Leaching as an Efficient Tool for Constructing New Catalytic Reactions: Application to the Synthesis of Cyclic Vinyl Sulfides and Vinyl Selenides

Radical ring‐opening polymerization of lipoates: Kinetic and thermodynamic aspects

TD-DFT Calculations, NBO, NLO Analysis and Electronic Absorption Spectra of Some Novel Thiazolo[3,2-a]Pyridine Derivatives Bearing Anthracenyl Moiety

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