Ueber das Amidotriazsulfol

The ultraviolet absorption spectra of 5-(substituted)ami~lo-1,2,3,4-thiatriazls and the corresponding ison~eric I-substituted-tetrazoline-5-thiones have been studied. The spectra and the dipole moments of the 5-(substituted)amino-1,2,3,4-thiatriazoles eliminate the possibility of meso-ionic structures for these compounds. The dipole moments of 5-amino-, 5-methylamino-, and 5-dimethylamino-1,2,3,4-thiatriazole were all high but approximately of the same value (5.77 to 5.84 D). This suggests that the amino thiatriazoles are best represented by conventional covalent structures with significant ionic resonance contributions. The thiatriazole ring system exhibits a characteristic absorption maximum a t 250-255 m r and an electron-withdrawing effect approximately equal to the tetrazolyl ring system. The tetrazolinethionolyl ring system is similarly electron-withdrawing. The relative acidities of the I-substituted-tetrazoline-5-thiones and the 5-alkylmercaptotetrazoles have also been studied and the results support the observations made on the basis of their ultraviolet absorption spectra. INTRODUCTIONIn recent communications, Lieber and co-workers (1, 2) reported upon the formation and chemistry of 5-(substituted)amino-1,2,3,4-thiatriazole, I , and the corresponding isomeric 1-substituted-tetrazoline-5-thiones, I1 (R2 = I-I). 5-Amino-1,2,3,4-thiatriazole3(1, 3, 4) (I, R1 = R2 = H) has a high melting point (128-130°, decomp.), a well-defined crystalline character, and is easily soluble in water. I n general, the crystalline character and relatively high melting points extend to the 5-(substituted)amino-1,2,3,4-thiatriazoles (I, R1 = (substituted)aryl; R2 = H) and the corresponding isomeric l-substitutedtetrazoline-5-thiones (11, R1 = (substituted)aryl; R2 = H) (I). This behavior has been explained by the proposal (I) that compounds of structure 1 (R" H ) exist a s a tautomeric mixture probably in zwitterioil form, the latter being best expressed as a meso-ionic ~t r u c t u r e ,~ I11 (R3 = H ) :

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“…2,3,3,4) (I, R1 = R2 = H) has a high melting point (128-130°, decomp. ), a well-defined crystalline character, and is easily soluble in water.…”

Section: Introductionmentioning

confidence: 99%

Ultraviolet Absorption Spectra and Acidities of Isomeric Thiatriazole and Tetrazole Derivatives

Lieber¹,

Ramachandran²,

Rao³

et al. 1959

Can. J. Chem.

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“…Cyanamide forms colorless, deliquescent orthorhombic crystals or long transparent needles (from water) [33], large platelike crystals when allowed to crystallize spontaneously from water, and crystals from dimethyl phthalate solution [34]. The crystal structure of solid cyanamide has been thoroughly investigated [35].…”

Section: Physical Properties [6]mentioning

confidence: 99%

Cyanamides

Güthner¹,

Mertschenk²

2006

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Calcium Cyanamide 1.1. Physical Properties 1.2. Chemical Properties 1.3. Production 1.3.1. Overall Process 1.3.2. Manufacture 1.3.3. Processing of Technical Calcium Cyanamide 1.4. Quality Specifications 1.5. Storage and Transportation 1.6. Uses 1.7. Legal Aspects 2. Cyanamide 2.1. Physical Properties 2.2. Chemical Properties 2.3. Production 2.4. Analysis 2.5. Storage and Transportation 2.6. Uses 2.7. Legal Aspects 3. Dicyandiamide 3.1. Physical Properties 3.2. Chemical Properties 3.3. Production 3.4. Quality Specifications and Analysis 3.5. Storage and Transportation 3.6. Uses 3.7. Legal Aspects 4. Substituted Cyanamides 5. Toxicology and Occupational Health Calcium cyanamide is produced from calcium carbide and nitrogen gas by an exothermic solid nitrogenation at 1000°C. It is used as a slow release nitrogen fertilizer with beneficial side effects against soilborne deseases. In chemical industry, it is the base for cyanamide and thiourea chemistry. Cyanamide is a fairly stable, toxic substance obtained from calcium cyanamide by reaction with water and carbon dioxide. It has vast applications in industrial nitrogen organic chemistry, and is also directly used as a plant protection agent. Dicyandiamide is derived from cyanamide by dimerization in presence of alkali. The nontoxic compound has found widespread industrial applications in resins, plastics, water treatment, and pharmaceuticals.

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“…5-amino-l,2,3,4-thiatriazole decomposes on heating and the formation of dicyanamide can be detected [6,7]. The thermal decompositions of other 5-(subst)-amino-l,2,3,4-thiatriazoles have not been studied until now.…”

mentioning

confidence: 97%

“…According to several references [6,7], the thermal decompositions of 5-(subst)--1,2,3,4-thiatriazoles proceed in the following way:…”

mentioning

confidence: 99%

Thermal properties of 5-(subst)-amino-1,2,3,4-thiatriazoles

Floch

Martvoň

Košík

1977

Journal of Thermal Analysis

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The thermal properties of 5-(subst)-amino-l,2,3,4-thiatriazoles were studied using TG and DTA. 5-amino-l,2,3,4-thiatriazole was actively decomposed at the melting temperature. The active thermal decomposition proceeds at a very fast rate, being accompanied by exothermic reactions of recombination. In comparison with this, the different-5-(subst)-amino-l,2,3,4-thiatriazoles are decomposed at slower rates in several degradative steps. The effects of some substituents on the total course of thermal degradation are discussed.

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Ueber das Amidotriazsulfol

Cited by 42 publications

References 2 publications

Ultraviolet Absorption Spectra and Acidities of Isomeric Thiatriazole and Tetrazole Derivatives

Ultraviolet Absorption Spectra and Acidities of Isomeric Thiatriazole and Tetrazole Derivatives

Cyanamides

Thermal properties of 5-(subst)-amino-1,2,3,4-thiatriazoles

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