ChemInform Abstract: REACTION OF MELEM WITH FORMALDEHYDE

Spasskaya, R. I.; Finkel'shtein, A. I.; Zil'berman, E. N.; Gal'perin, V. A.

doi:10.1002/chin.197637269

Cited by 3 publications

(3 citation statements)

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“…Spasskaya et al. described the reaction with formaldehyde16 leading to the formation of a methanol‐substituted melem derivative. A second example of a nucleophilic reaction of the amino groups of melem is the Kirsanov reaction of melem with PCl 5 to form the triphosphinimino derivative [C 6 N 7 (NPCl 2 ) 3 ] 5c.…”

Section: Introductionmentioning

confidence: 99%

Use of Melem as a Nucleophilic Reagent to Form the Triphthalimide C₆N₇(phthal)₃—New Targets and Prospects

Schwarzer

Böhme

Kroke

2012

Chemistry A European J

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Melem (1), as one of the most important representatives of the tri-s-triazine compounds, can be used as a nucleophilic reagent in reactions with phthalic acid derivatives. The synthesis of 2,5,8-triphthalimido-tri-s-triazine (C(6)N(7)(phthal)(3), 2) was investigated starting from phthalic anhydride or phthalic dichloride in various solvents, at different temperatures as well as in the solid state. NMR measurements (solution and solid state), IR spectroscopy and elemental analysis indicated the formation of a cyclic imide. Single-crystal structure analysis of a 1:1 adduct of 2 with nitromethane proved the molecular structure expected for a phthalimido-s-heptazine. DFT calculations were performed to obtain a better insight into the structural features of compound 2, especially the interaction of the carbonyl groups with the tri-s-triazine nitrogen atoms. The title compound 2 shows promising properties: it is thermally stable up to 500 °C in air and shows strong photoluminescence with a maximum emission at around 500 nm. The potential of the nucleophilic reaction of melem with other strong electrophiles provides new targets and prospects.

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Section: Introductionmentioning

confidence: 99%

Use of Melem as a Nucleophilic Reagent to Form the Triphthalimide C₆N₇(phthal)₃—New Targets and Prospects

Schwarzer

Böhme

Kroke

2012

Chemistry A European J

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“…Syntheses using Me were challenging, due to the low reactivity and solubility of Me in water, and this presented further issues to those already encountered with M, and required additional modifications to the experimental procedure. As a result of the planar structure of the ring formation, the nucleophilicity of the amino groups is low [16], and reactions involving the amino groups as nucleophilic reagents are very rare [17]. This previous work informed the modifications made here, where the reaction between Me and F was promoted at elevated temperatures (80-130 • C), and~90 • C was used in this study as the reaction medium is water.…”

Section: Melem Composite Gelsmentioning

confidence: 68%

Effect of Aromatic Amines on the Properties of Formaldehyde-Based Xerogels

Martin

Prostredny

Fletcher

2020

Gels

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This study investigates the synthesis of formaldehyde-based xerogels using alternative aromatic precursors, with comparison to traditional resorcinol-formaldehyde analogues, in order to alter the chemical composition of the resulting gels. By replacing resorcinol with aromatic amine molecules, i.e., ammeline, melamine and melem, each expected to undergo similar reactions with formaldehyde as the substituted species, we found that for all substituted gels, at low additive contents, the gel structure was compromised and non-porous materials were formed, as opposed to the most abundant monomers, and therefore, these additives seem to act as impurities at low levels. Working towards higher additive contents, melem monomers exhibited low solubility (~5%), even at elevated temperatures, thereby limiting the range to which melem could act as a substitute, while melamine could be incorporated up to ~40% under acidic conditions, with enhanced microporosity over this range. Pure gels were successfully synthesised from ammeline, but their performance was inferior to resorcinol-formaldehyde gels, while melamine-formaldehyde analogues required acidic reaction conditions but shrank considerably on sub-critical drying, adversely affecting the gel properties and demonstrating their lack of potential as sorbents. This demonstrates the potential for the inclusion of aminated aromatics within resorcinol-based gel systems, however, only as partial substitutes and not complete replacements.

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“…72 After Redemann and Lucas, Finkel'shtein of the Soviet Union explored the spectroscopic and thermal properties of these known cyameluric molecules over the next forty years. [73][74][75][76][77][78][79][80][81][82][83][84][85] They did much to advance the understanding of melem, hydromelonic acid and others, although no new derivatives were reported. It was also during this time they began referring to the cyameluric nucleus as "sym-heptazine" for the seven nitrogen atoms it contained.…”

Section: Heptazine: Beyond Triazine-based C-n Structuresmentioning

confidence: 99%

Synthesis of inorganic heptazine-based materials

Holst¹

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This dissertation describes research on the synthesis and characterization of extended heptazine-based, graphite-like carbon nitride materials (CN x), as well as molecular heptazine (C 6 N 7) derivatives. Spurred on by recent triazine to heptazine conversion studies, a structural examination was performed on an amorphous nitrogenrich carbon nitride material formed via the rapid and exothermic self-propagating decomposition of a triazine (C 3 N 3) precursor, trichloromelamine (TCM). The thermally stable and insoluble CN x H y product was determined to be composed of heptazine repeat units. This conclusion was supported by 13 C solid state NMR and isolation of molecular heptazine anions after base hydrolysis (structural deconstruction) of the CN x H y material. Modifications to the decomposition of TCM were explored. Introduction of a solid template (NaCl or silica) led to morphological changes in the TCM-CN x product, observed by scanning electron microscopy. It was found that the sodium salts, NaBr and NaN 3 , led to chloride exchange with TCM. The use of mixtures of NH 4 Cl and NaN 3 also showed changes in the morphology of the material, while leading to slight changes in the IR spectra. A series of reactions between NaBH 4 and TCM yield novel thermally stable boron carbon nitride (BCN) materials. Reactions between TCM and Li 2 C 2 or aromatic organic solids led to CN x materials with increased carbon contents. Crystalline metal-heptazine precipitates were generated by cation exchange reaction with the base hydrolysis product of TCM-CN x , potassium cyamelurate. A structure solution was attempted for the crystalline copper cyamelurate salt, KCu[C 6 N 7 O 3 ]•4H 2 O. Neutral molecular heptazines were also synthesized; these species included 2,5,8-tribromo-s-heptazine (TBH), 2,5,8-triphenyl-s-heptazine (TPH), 2,5,8ix Solid state NH 4 Cl/NaN 3 and NaHCO 3 incorporation into trichloromelamine decomposition: Gas-forming additives .

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ChemInform Abstract: REACTION OF MELEM WITH FORMALDEHYDE

Abstract: Melem (I) reagiert mit überschüssigem Formaldehyd zum Trimethylolmelem (II).

Cited by 3 publications

References 0 publications

Use of Melem as a Nucleophilic Reagent to Form the Triphthalimide C₆N₇(phthal)₃—New Targets and Prospects

Use of Melem as a Nucleophilic Reagent to Form the Triphthalimide C₆N₇(phthal)₃—New Targets and Prospects

Effect of Aromatic Amines on the Properties of Formaldehyde-Based Xerogels

Synthesis of inorganic heptazine-based materials

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ChemInform Abstract: REACTION OF MELEM WITH FORMALDEHYDE

Abstract: Melem (I) reagiert mit überschüssigem Formaldehyd zum Trimethylolmelem (II).

Cited by 3 publications

References 0 publications

Use of Melem as a Nucleophilic Reagent to Form the Triphthalimide C6N7(phthal)3—New Targets and Prospects

Use of Melem as a Nucleophilic Reagent to Form the Triphthalimide C6N7(phthal)3—New Targets and Prospects

Effect of Aromatic Amines on the Properties of Formaldehyde-Based Xerogels

Synthesis of inorganic heptazine-based materials

Contact Info

Product

Resources

About

Use of Melem as a Nucleophilic Reagent to Form the Triphthalimide C₆N₇(phthal)₃—New Targets and Prospects

Use of Melem as a Nucleophilic Reagent to Form the Triphthalimide C₆N₇(phthal)₃—New Targets and Prospects