Triazolium salt

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Triazolium salts

Two groups of triazolium salts based on the central triazole ring isomer

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Triazolium salts-isomers.png

Triazolium salts are chemical compounds based on the substituted triazole structural element. They are composed of a cation based on a heterocyclic five-membered ring with three nitrogen atoms, two of which are functionalized and a corresponding counterion (anion). Depending on the arrangement of the three nitrogen atoms the triazolium salts are divided into two isomers, namely 1,3,4-trisubstituted-1H-1,2,3-triazolium salts as well as 1,2,4-triazolium salts. They are precursors for the preparation of N-heterocylcic carbenes. [1]

1,3,4-trisubstituted-1H-1,2,3-triazolium salts

1,4-disubstituted 1,2,4-triazolium salts

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A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles.

Tetrazine is a compound that consists of a six-membered aromatic ring containing four nitrogen atoms with the molecular formula C2H2N4. The name tetrazine is used in the nomenclature of derivatives of this compound. Three core-ring isomers exist: 1,2,3,4-tetrazines, 1,2,3,5-tetrazines, and 1,2,4,5-tetrazines, also known as v-tetrazines, as-tetrazines and s-tetrazines respectively.

<span class="mw-page-title-main">Imidazole</span> Chemical compound

Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution.

In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is R−:C−R' or R=C: where the R represents substituents or hydrogen atoms.

<span class="mw-page-title-main">HU-210</span> Chemical compound

HU-210 is a synthetic cannabinoid that was first synthesized in 1988 from (1R,5S)-myrtenol by a group led by Raphael Mechoulam at the Hebrew University. HU-210 is 100 to 800 times more potent than natural THC from cannabis and has an extended duration of action. HU-210 has a binding affinity of 0.061nM at CB1 and 0.52nM at CB2 in cloned human cannabinoid receptors compared to Delta-9-THC of 40.7nM at CB1. HU-210 is the (–)-1,1-dimethylheptyl analog of 11-hydroxy- Δ8- tetrahydrocannabinol; in some references it is called 1,1-dimethylheptyl- 11-hydroxytetrahydrocannabinol. The abbreviation "HU" stands for Hebrew University.

Thiazole, or 1,3-thiazole, is a heterocyclic compound that contains both sulfur and nitrogen. The term 'thiazole' also refers to a large family of derivatives. Thiazole itself is a pale yellow liquid with a pyridine-like odor and the molecular formula C3H3NS. The thiazole ring is notable as a component of the vitamin thiamine (B1).

<span class="mw-page-title-main">Triazine</span> Aromatic, heterocyclic compound

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1,2,3-Triazole is one of a pair of isomeric chemical compounds with molecular formula C2H3N3, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,3-Triazole is a basic aromatic heterocycle.

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The triazol-5-ylidenes are a group of persistent carbenes which includes the 1,2,4-triazol-5-ylidene system and the 1,2,3-triazol-5-ylidene system. As opposed to the now ubiquitous NHC systems based on imidazole rings, these carbenes are structured from triazole rings. 1,2,4-triazol-5-ylidene can be thought of as an analog member of the NHC family, with an extra nitrogen in the ring, while 1,2,3-triazol-5-ylidene is better thought of as a mesoionic carbene (MIC). Both isomers of this group of carbenes benefit from enhanced stability, with certain examples exhibiting greater thermal stability, and others extended shelf life.

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HU-243 (AM-4056) is a synthetic cannabinoid drug that is a single enantiomer of the hydrogenated derivative of the commonly used reference agonist HU-210. It is a methylene homologue of canbisol. It is a potent agonist at both the CB1 and CB2 receptors, with a binding affinity of 0.041 nM at the CB1 receptor, making it marginally more potent than HU-210, which had an affinity of 0.061 nM in the same assay.

<span class="mw-page-title-main">1,1'-Azobis-1,2,3-triazole</span> Chemical compound

1,1-Azobis-1,2,3-triazole is a moderately explosive but comparatively stable chemical compound which contains a long continuous chain of nitrogen atoms, with an unbroken chain of eight nitrogen atoms cyclised into two 1,2,3-triazole rings. It is stable up to 194 °C. The compound exhibits cis–trans isomerism at the central azo group: the trans isomer is more stable and is yellow, while the cis isomer is less stable and is blue. The two rings are aromatic and form a conjugated system with the azo linkage. This chromophore allows the trans compound to be isomerised to the cis when treated with an appropriate wavelength of ultraviolet light.

In chemistry, mesoionic carbenes (MICs) are a type of reactive intermediate that are related to N-heterocyclic carbenes (NHCs); thus, MICs are also referred to as abnormal N-heterocyclic carbenes (aNHCs) or remote N-heterocyclic carbenes (rNHCs). Unlike simple NHCs, the canonical resonance structures of these carbenes are mesoionic: an MIC cannot be drawn without adding additional charges to some of the atoms.

<span class="mw-page-title-main">SIMes</span> Chemical compound

SIMes (or H2Imes) is an N-heterocyclic carbene. It is a white solid that dissolves in organic solvents. The compound is used as a ligand in organometallic chemistry. It is structurally related to the more common ligand IMes but with a saturated backbone (the S of SIMes indicates a saturated backbone). It is slightly more flexible and is a component in Grubbs II. It is prepared by alkylation of trimethylaniline by dibromoethane followed by ring closure and dehydrohalogenation.

A triazolate is a salt derived from a triazole by replacement of a proton with a cation. Different isomers exist 1,2,4-triazolate or 1,2,3-triazolate, both of which are unsaturated heterocyclic ring compounds containing three nitrogen atoms. The basic formula is C2N3H2. It can be abbreviated by "tz".

References

  1. Nolan, Steven P. (2006). Nolan, Steven P (ed.). N-Heterocyclic Carbenes in Synthesis. Verlag: Wiley-VCH. doi:10.1002/9783527609451. ISBN   978-3-527-60940-6.