1,2,3,4-Thiatriazoles

Dehaen, Wim; Бакулев, В. А.

doi:10.1016/b978-008044992-0.00519-8

Cited by 2 publications

(6 citation statements)

References 143 publications

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“…N 2 -N 3 and N 4 -C 5 bonds, nominally double bonds, are between a single and a double bonds (bond order 1.81 and 1.78, respectively), and S 1 -N 2 , N 3 -N 4 , and C 5 -S 1 bonds, nominally single bonds, are shorter than a S-N, N-N, or C-S single bond (bond order 1.11, 1.35, and 1.48, respectively). This tendency to bond order equalization is in agreement with the expected aromaticity of thiatriazoles [6,7]. This corroborates with the calculated nucleus independent chemical shift values of NICS(0) = -11.1 and NICS(1) = -11.2 (B3LYP/aug-cc-pVTZ).…”

Section: Resultssupporting

confidence: 89%

“…The only known halogen derivative, the 5-chloro-1,2,3,4-thiatriazole is highly explosive [8]. It has been used in nucleophilic reactions for the synthesis of substituted amino-and alkoxy-thiatriazoles [6][7][8]. Very little is known experimentally about the structure of unstable thiatriazoles, and 5-chloro-1,2,3,4-thiatriazole has never been studied by any experimental or theoretical methods to date.…”

mentioning

confidence: 97%

“…Very little is known experimentally about the structure of unstable thiatriazoles, and 5-chloro-1,2,3,4-thiatriazole has never been studied by any experimental or theoretical methods to date. Structure and properties of a few relatively stable aryl-, amino-, and thio-derivatives have been studied by X-ray crystallography, NMR, IR, UV, and Raman spectroscopy (see reviews [6,7] and references cited therein).…”

mentioning

confidence: 99%

“…Their thermal stability, however, strongly depends on the substituent attached to the ring carbon atom. Aryl and substituted amino-and thio-derivatives are relatively stable and have found applications due to their interesting biological properties, including fungicidal, antitubercular, antiviral, anticancer, and muscle stimulant activity [7]. Alkyl, aralkyl, and alkoxy derivatives are unstable, isolated only at low temperature, and often present explosion danger at ordinary conditions [3][4][5][6][7].…”

mentioning

confidence: 99%

“…A wide range of organic derivatives have been prepared following the 1950s [3][4][5][6][7]. Thiatriazoles are known to be thermally unstable and decompose upon mild heating or even at room temperature to sulfur, nitrogen, and nitriles.…”

mentioning

confidence: 99%

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Structure, spectroscopy, and thermal decomposition of 5-chloro-1,2,3,4-thiatriazole: a He I photoelectron, infrared, and quantum chemical study

et al. 2015

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International audience5-Chloro-1,2,3,4-thiatriazole has been investigated in the gas phase for the first time by mid-infrared and He I photoelectron spectroscopy. The ground-state geometry has been obtained from quantum chemical calculations at the CCSD(T) and B3LYP levels using aug-cc-pVTZ basis set. Ionization potentials have been determined and the electronic structure has been discussed within the frame of molecular orbital theory. IR and photoelectron spectroscopies, supported by quantum chemical calculations at the B3LYP and SAC-CI levels, provide a detailed investigation into the vibrational and electronic character of the molecule. Thermal stability of 5-chloro-1,2,3,4-thiatriazole has been studied both experimentally and theoretically. Flash vacuum thermolysis of the molecule produces fast quantitatively N2, ClCN, and sulfur. Theoretical calculations at the CCSD(T)//B3LYP level predict competitive decomposition routes, starting either with a retro-cycloaddition reaction leading to N2S and ClCN or with a ring opening to chlorothiocarbonyl azide intermediate, to produce finally N2, S, and ClCN. Calculations also predict that N2S is reactive and decomposes in bimolecular reactions to N2 and S

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Section: Resultssupporting

confidence: 89%

mentioning

confidence: 97%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Structure, spectroscopy, and thermal decomposition of 5-chloro-1,2,3,4-thiatriazole: a He I photoelectron, infrared, and quantum chemical study

et al. 2015

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Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides

Ilkin¹,

Berseneva²,

Beryozkina³

et al. 2020

Beilstein J. Org. Chem.

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N-Sulfonyl amidines bearing 1,2,3-triazole, isoxazole, thiazole and pyridine substituents were successfully prepared for the first time by reactions of primary, secondary and tertiary heterocyclic thioamides with alkyl- and arylsulfonyl azides. For each type of thioamides a reliable procedure to prepare N-sulfonyl amidines in good yields was found. Reactions of 1-aryl-1,2,3-triazole-4-carbothioamides with azides were shown to be accompanied with a Dimroth rearrangement to form 1-unsubstituted 5-arylamino-1,2,3-triazole-4-N-sulfonylcarbimidamides. 2,5-Dithiocarbamoylpyridine reacts with sulfonyl azides to form a pyridine bearing two sulfonyl amidine groups.

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1,2,3,4-Thiatriazoles

Cited by 2 publications

References 143 publications

Structure, spectroscopy, and thermal decomposition of 5-chloro-1,2,3,4-thiatriazole: a He I photoelectron, infrared, and quantum chemical study

Structure, spectroscopy, and thermal decomposition of 5-chloro-1,2,3,4-thiatriazole: a He I photoelectron, infrared, and quantum chemical study

Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides

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