The thermal decomposition of tetrazoles

Лесникович, А. И.; Levchik, Sergei V.; Balabanovich, A.I.; Ивашкевич, Олег А.; Гапоник, П. Н.

doi:10.1016/0040-6031(92)85135-i

Cited by 65 publications

(43 citation statements)

References 66 publications

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“…These two signals showed providing fast relaxation of the energy of thermal excitation of heterocycles. [20] Figure 5 shows that under nitrogen purge and with a heating rate of 10 °C/min, the decomposition of MTZ100-PIM was accompanied by three stages, whereas TZ-PIM only showed two stages of decomposition. propose a plausible degradation process to explain the three-step degradation curve for the MTZ groups.…”

Section: Resultsmentioning

confidence: 99%

“…It is known that the 2-alkyl-form tetrazole is less thermostable than the 1-alkyl-form tetrazole, because N 2 readily splits off, resulting in nitrilimine formation during the initial stage of decomposition. [20] It is also known that alkyl-form tetrazoles split off into alkyl azide during the thermolysis of 1-alkyl-form tetrazole, but rarely in the case of 2-alkyl-form. [20] We observed a strong MS signal for m/e 57, which is present only during the 2 nd degradation step and which could originate from methyl azide groups.…”

Section: Resultsmentioning

confidence: 99%

“…[20] It is also known that alkyl-form tetrazoles split off into alkyl azide during the thermolysis of 1-alkyl-form tetrazole, but rarely in the case of 2-alkyl-form. [20] We observed a strong MS signal for m/e 57, which is present only during the 2 nd degradation step and which could originate from methyl azide groups.…”

Section: Resultsmentioning

confidence: 99%

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Polymers of intrinsic microporosity (PIMs) substituted with methyl tetrazole

Robertson

Dal‐Cin

et al. 2012

Polymer

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Polymers of intrinsic microporosity (PIMs) substituted with methyl tetrazole Du, Naiying; Robertson, Gilles P.; Dal-Cin, Mauro M.; Scoles, Ludmila; Guiver, Michael D. Polymers of Intrinsic AbstractA polymer of intrinsic microporosity (PIM-1) containing nitrile groups was reacted by [2 + 3] cycloaddition reaction to give a polymer substituted with tetrazole groups (TZ-PIM), and then was further methylated to give a new PIM substituted with methyl tetrazole groups (MTZ-PIM). In contrast to TZ-PIMs, the MTZ-PIMs had distinctly improved solubility characteristics, enabling a more detailed investigation of the degree of conversion for the cycloaddition reaction and the structures of TZ-PIMs, which showed the presence of two kinds of tetrazole rings. Compared with PIM-1, the MTZ-PIM showed higher gas permselectivity with a corresponding decrease in gas permeability for pure gas pairs such as O 2 /N 2 and CO 2 /N 2 , and for mixed gases, such as CO 2 /N 2 . Data for selectivity coupled with high gas permeability is close to the Robeson 2008 upper-bound performance limit for the O 2 /N 2 and CO 2 /N 2 pure gas pairs, and exceeds the upper-bound for the CO 2 /N 2 mixed gas pair.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Polymers of intrinsic microporosity (PIMs) substituted with methyl tetrazole

Robertson

Dal‐Cin

et al. 2012

Polymer

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“…The thermal decomposition of tetrazole has also gained attention [13] tetrazole-based compounds as potential explosive materials, electric igniters and solid rocket propellant formulations [14]. The explosive properties of tetrazoles are related to their molecular and electronic structure, the ranking in explosive behavior of 5-substituted tetrazoles correlates with the electron withdrawing capacity of the substituents [15].…”

Section: Introductionmentioning

confidence: 99%

A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester

Saeed

Qasim

Hussain

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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The tautomeric and conformational properties of a new tetrazole derivative are studied in a combined approach that includes the analysis of the experimental vibrational data together with theoretical calculation methods, especially in terms of natural bond orbital (NBO) population analysis. Moreover, the molecular and crystal structure was determined by single crystal X-ray diffraction. The compound crystallized as the 2-tautomeric form, monoclinic space group P21/c with Z=4, a=10.0630(14), b=8.2879(11), c=12.8375(18) Å, β=105.546(3)°, V=1031.5(2) Å(3). The tetrazole and phenyl rings are coplanar with the acetate group oriented perpendicular to the plane. The NBO analysis showed that delocalizing interactions of the lpp(N2) lone pair orbital contributes to a strong resonance interactions with both adjacent π(∗)(N3N4) and π(∗)(N1C5) antibonding orbitals of the tetrazole group.

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“…[ 11 ] Most of the tetrazoles show moderate thermal stability below 200 °C, while decomposing at higher temperature with the formation of a high proportion of gaseous products. [ 12 ] Based on these properties, Murray, Shevchenko and Talapin patented tetrazoles as removable stabilizing agents for the preparation of organic surfactant-free nanostructures, which might be of interest due to their high electroconductivity and catalytic activity. [ 13 ] This review presents recent developments in the application of tetrazole derivatives in the preparation of nanostructured materials.…”

Section: Introductionmentioning

confidence: 99%

Tetrazoles: Unique Capping Ligands and Precursors for Nanostructured Materials

Войтехович

Lesnyak

Gaponik

et al. 2015

Small

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Capping agents play an important role in the colloidal synthesis of nanomaterials because they control the nucleation and growth of particles, as well as their chemical and colloidal stability. During recent years tetrazole derivatives have proven to be advanced capping ligands for the stabilization of semiconductor and metal nanoparticles. Tetrazole-capped nanoparticles can be prepared by solution-phase or solventless single precursor approaches using metal derivatives of tetrazoles. The solventless thermolysis of metal tetrazolates can produce both individual semiconductor nanocrystals and nanostructured metal monolithic foams displaying low densities and high surface areas. Alternatively, highly porous nanoparticle 3D assemblies are achieved through the controllable aggregation of tetrazole-capped particles in solutions. This approach allows for the preparation of non-ordered hybrid structures consisting of different building blocks, such as mixed semiconductor and metal nanoparticle-based (aero)gels with tunable compositions. Another unique property of tetrazoles is their complete thermal decomposition, forming only gaseous products, which is employed in the fabrication of organic-free semiconductor films from tetrazole-capped nanoparticles. After deposition and subsequent thermal treatment these films exhibit significantly improved electrical transport. The synthetic availability and advances in the functionalization of tetrazoles necessitate further design and study of tetrazole-capped nanoparticles for various applications.

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The thermal decomposition of tetrazoles

Cited by 65 publications

References 66 publications

Polymers of intrinsic microporosity (PIMs) substituted with methyl tetrazole

Polymers of intrinsic microporosity (PIMs) substituted with methyl tetrazole

A combined experimental and theoretical study of the tautomeric and conformational properties of (5-phenyl-tetrazol-2-yl)-acetic acid methyl ester

Tetrazoles: Unique Capping Ligands and Precursors for Nanostructured Materials

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