Tetrazine is a
compound that consists of a six-membered
aromatic
In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...
ring containing four nitrogen atoms with the molecular formula
C2 H2 N4. The name ''tetrazine'' is used in the
nomenclature
Nomenclature (, ) is a system of names or terms, or the rules for forming these terms in a particular field of arts or sciences. (The theoretical field studying nomenclature is sometimes referred to as ''onymology'' or ''taxonymy'' ). The principl ...
of derivatives of this compound. Three core-ring
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
s 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.
1,2,3,4-Tetrazines
1,2,3,4-Tetrazines are often isolated fused to an aromatic ring system and are stabilized as the dioxide derivatives.
1,2,4,5-Tetrazines
1,2,4,5-Tetrazines are very well known and myriad 3,6-disubstituted 1,2,4,5-tetrazines are known. These materials are of use in the area of energetic chemistry.
Heavily substituted tetrazines form the
verdazyls, a family of
stable radicals.
Protected tetrazines are strong
acetylene
Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...
acceptors in
Diels-Alder equilibria. For example,
dipyridinyl 1,2,4,5-tetrazine abstracts acetylene from
norbornadiene to
cyclopentadiene
Cyclopentadiene is an organic compound with the chemical formula, formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp−.
This colorless liquid has a strong and unpleasant odor. At room temperature, ...
and a
pyridazine:
:
With norbornadiene fused to an arene the reaction stops at an intermediary stage.
[''π-Bond Screening in Benzonorbornadienes: The Role of 7-Substituents in Governing the Facial Selectivity for the Diels-Alder Reaction of Benzonorbornadienes with 3,6-Di(2-pyridyl)-s-Tetrazine''. Ronald N. Warrener and Peter A. Harrison ]Molecules
A molecule is a group of two or more atoms that are held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemistry ...
2001, 6, 353–36
Online Article
/ref>
See also
* 6-membered rings with one nitrogen atom: pyridine
Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weak ...
* 6-membered rings with two nitrogen atoms: diazines
* 6-membered rings with three nitrogen atoms: triazines
* 6-membered rings with five nitrogen atoms: pentazine
* 6-membered rings with six nitrogen atoms: hexazine
References
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