On the transfer of theoretical multipole parameters for restoring static electron density and revealing and treating atomic anharmonic motion. Features of chemical bonding in crystals of an isocyanuric acid derivative

The crystal and electronic structure of an isocyanuric acid derivative was studied by high-resolution single-crystal X-ray diffraction within the Hansen–Coppens multipole formalism. The observed deformation electron density shows signs of thermal smearing. The experimental picture meaningfully assigned to the consequences of unmodelled anharmonic atomic motion. Straightforward simultaneous refinement of all parameters, including Gram–Charlier coefficients, resulted in more significant distortion of apparent static electron density, even though the residual density became significantly flatter and more featureless. Further, the method of transferring multipole parameters from the model refined against theoretical structure factors as an initial guess was employed, followed by the subsequent block refinement of Gram–Charlier coefficients and the other parameters. This procedure allowed us to appropriately distinguish static electron density from the contaminant smearing effects of insufficiently accounted atomic motion. In particular, some covalent bonds and the weak π...π interaction between isocyanurate moieties were studied via the mutual penetration of atomic-like kinetic and electrostatic potential φ-basins with complementary atomic ρ-basins. Further, local electronic temperature was applied as an advanced descriptor for both covalent bonds and noncovalent interactions. Total probability density function (PDF) of nuclear displacement showed virtually no negative regions close to and around the atomic nuclei. The distribution of anharmonic PDF to a certain extent matched the residual electron density from the multipole model before anharmonic refinement. No signs of disordering of the sulfonyl group hidden in the modelled anharmonic motion were found in the PDF.

Isocyanuric acid-modified cyclohexanone–formaldehyde resins for fire-retardant polyurethane

Purpose Cyclohexanone–formaldehyde resin (CFR) was in situ modified with isocyanuric acid (ICA) in the presence of hydrochloric acid or p-toluenesulfonic acid by condensation polymerization. The purpose of this study is to produce isocyanuric acid-modified ketonic resins that have higher melting and decomposition temperature, and to use the produced resin in the production of fire-retardant polyurethane. Design/methodology/approach Two methods were used for in situ preparation of ICA-modified CFR in the presence of an acid catalyst. Method I: cyclohexanone, paraformaldehyde and ICA were mixed, and then an acid catalyst was added to form the modified CFR. Method II: ICA and formalin were mixed to produce N, N, N-trihydroxymethyl isocyanurate, and then water was removed under vacuum. The produced N, N, N-trihydroxymethyl isocyanurate solution was mixed with cyclohexanone and paraformaldehyde, then an acid catalyst was slowly added to this mixture to obtain ICA-modified CFR. Findings CFR was prepared in the presence of an acid catalyst. The product, CFR, has a dark red colour. The resulting resins have similar physical properties with the resin prepared in the presence of a basic catalyst. The solubility of ICA-modified CFR is much different than CFR in organic solvents. Research limitations/implications This study focuses on obtaining an ICA-modified ketonic resin. Cyanuric acid has the form of an enolic structure under a basic condition; therefore, it cannot give a product with formaldehyde under basic conditions. The modification experiments were carried out in acidic conditions. Practical implications This study provides technical information for in situ modification of ketonic resin in the presence of acid catalysts. The resins may also promote the adhesive strength of the coating and provide corrosion inhibition on metal surfaces for a coating. The modified resins may also be used in the field of fire-retardant polyurethane applications. Social implications These resins may be used for the preparation of non-toxic fire-retardant polyurethane foam. Polyurethane containing ICA-modified resin may exhibit better fire-retardant performance because of the incorporation of ICA molecule into the polyurethane structure. Originality/value ICA-modified CFRs have been synthesized in the presence of an acid catalyst, and the ICA-modified resin was used to produce fire-retardant polyurethane.

Effecting Partial Elimination of Isocyanuric Acid from Swimming Pool Water Systems

It is essential to disinfect the water in swimming pools in order to deactivate pathogenic microorganisms. Chlorination of swimming pool water provides rapid and long-lasting disinfection, but leads to the formation of potentially toxic compounds, including isocyanuric acid, that are used to stabilize chlorine in pool water. Hygiene and health guidelines require an isocyanuric acid concentration in swimming pools of 25 to 75 ppm and that there be no level in excess of 100 ppm. This paper provides a new method to partially remove isocyanuric acid from the water of swimming pool systems with the use of melamine-based reagents. A melamine-photometry process stabilizes the isocyanuric acid. The melamine-based reagent that is added to the raw water reacts with the isocyanuric acid and forms a precipitated salt. The reaction also creates turbidity that is proportional to the isocyanuric acid concentration in the water. It was noted in this study that the optimum functioning range of melamine doses in the raw water was 0.04 to 0.06 g/L and that the reduction of isocyanuric acid in raw water increased as the dose of melamine was increased. Thus, it is necessary to obtain an estimate of the dose of melamine that is necessary to reduce the isocyanuric acid in the water without needing to add fresh water from the network to dilute it. Finally, it can be stated that eliminating isocyanuric acid that has accumulated in a pool’s water by treatment with melamine provides an efficient process, as it eliminates the amount of isocyanuric acid that is necessary to conform to the human health criteria of the European Union Directive 2006/7/EC. Treatment with melamine also reduces water network consumption and sewer discharge by successive purges that eventually will become unnecessary. Therefore, this proposed method is environmentally and economically beneficial.

Design of a Device to Eliminate Isocyanuric Acid from Water

This paper shows the design of a device for partial eliminating of isocyanuric acid (ICN) from swimming pool water using melamine additives. The renewal process of swimming pool water through its own purification makes absolutely necessary the elimination of isocyanuric acid that has been accumulated in the water over time. An excess of isocyanuric acid in water will then prevent chlorine effectiveness in the pool water and as a result, becomes harmful to human health. Therefore, the disinfection stage is considered as well as Isocyanuric acid (ICN) stabilization and as doing this is achieved through melamine-photometry filtering of insoluble complex ICN-M. The overall objective of these stages of purification is to eventually eliminate ICN from swimming pool. The overall objective of this device is to eventually eliminate ICN from swimming pool and then make it safe for human uses, a case that has been considered viable technologically and economically in the system treatment.

Density functional theory, Comparative vibrational spectroscopic studies, HOMO-LUMO, and NBO analysis of Trichloro isocyanuric acid and Trithio cyanuric acid

The molecular vibrations of Trichloro isocyanuric acid (C3Cl3N3O3) and Trithio cyanuric acid (C3H3N3S3) have been investigated in polycrystalline sample at room temperature by Fourier Transform Infrared (FT-IR) and FT-Raman spectroscopies in the region 4000-450 cm-1 and 4000-50 cm-1 respectively, which provide a wealth of structural information about the molecules. The spectra are interpreted with the aid of normal co-ordinate analysis following full structure optimization and force field calculations based on density functional theory  (DFT) using standard B3LYP / 6-311++ G (d, p) basis set for investigating the structural and spectroscopic properties. The vibrational frequencies are calculated and the scaled values are compared with experimental FT-IR and FT-Raman spectra. The scaled theoretical wave numbers shows very good agreement with experimental ones. The complete vibrational assignments are performed on the basis of potential energy distribution (PED) of vibrational modes, calculated with scaled quantum (SQM) method. Stability of the molecule arising from hyper conjugative interactions, charge delocalization has been analyzed using natural bond orbital (NBO) analysis. The results show that change in electron density (ED) in σ* and π* anti-bonding orbitals and second order delocalization  energy (E2) confirm the occurrence of Intra molecular Charge Transfer (ICT) within the molecule. The thermodynamic properties like heat capacity, entropy, enthalpy and zero point energy have been calculated for the molecule. The frontier molecular orbitals have been visualized and the HOMO-LUMO energy gap has been calculated. The Molecular Electrostatic Potential (MEP) analysis reveals the sites for electrophilic attack and nucleophilic reactions in the molecule.

Synthesis, antibacterial and cytotoxic activity evaluation of hydroxyurea derivatives

5 Synthesis and biological evaluation of a series (N = 16) of cyclic and acyclic hydroxyurea derivatives, including benzotriazole-, isocyanuric acid- and biuret-containing compounds, are disclosed. 1-N-(benzyloxycarbamoyl)benzotriazole was used as a benzyloxyisocyanate donor, a useful intermediate in the preparation of substituted hydroxyurea. Antibacterial activities of synthesized hydroxyurea derivatives were tested on three E. coli strains, i.e., a strain susceptible to antibiotics, a strain resistant to macrolide antibiotics and a strain resistant to aminoglycoside antibiotics. Six compounds (three acyclic and three cyclic hydroxyureas) showed growth inhibition of the tested E. coli strains, with different specificity toward each strain. Results of the cytotoxic activity evaluation revealed that twelve out of sixteen test compounds were cytotoxic to human acute monocytic leukemia THP-1 and/or human acute T cell leukemia Jurkat cell line. 1-(N-hydroxycarbamoyl) benzotriazole () increased the metabolic activity of both cell lines. Two compounds, 1-(N-hydroxycarbamoyl) benzotriazole (5) and N,N’,N’’-trihydroxybiuret (15), were identified as potential NO donors.