Tetrazine is a
compound that consists of a six-membered
aromatic
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...
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 principles of naming vary from the relatively informal conventions of everyday speech to the internationally ag ...
of derivatives of this compound. Three core-ring
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Is ...
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-Tetrazine
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.
The compound 3,6-di-2-pyridyl-1,2,4,5-tetrazine' has two
pyridine
Pyridine is a basic 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, weakly alkaline, water-miscible liquid w ...
substituents and is of importance as a reagent in
Diels-Alder reactions. It reacts with
norbornadiene
Norbornadiene is an organic compound and a bicyclic hydrocarbon. Norbornadiene is of interest as a metal-binding ligand, whose complexes are useful for homogeneous catalysis. It has been intensively studied owing to its high reactivity and distin ...
in a sequence of one DA reaction and two retro-DA reactions to
cyclopentadiene
Cyclopentadiene is an organic compound with the formula C5H6.LeRoy H. Scharpen and Victor W. Laurie (1965): "Structure of cyclopentadiene". ''The Journal of Chemical Physics'', volume 43, issue 8, pages 2765-2766. It is often abbreviated CpH beca ...
and a
pyridazine with exchange of an
acetylene
Acetylene ( systematic name: ethyne) is the 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 unstable in its pure ...
unit:
:
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 held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bio ...
2001, 6, 353–36
Online Article
See also
* 6-membered rings with one nitrogen atom:
pyridine
Pyridine is a basic 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, weakly alkaline, water-miscible liquid w ...
* 6-membered rings with two nitrogen atoms:
diazine
In organic chemistry, diazines are a group of organic compounds having the molecular formula . Each contains a benzene ring in which two of the C-H fragments have been replaced by isolobal nitrogen. There are three structural isomers:
* pyridaz ...
s
* 6-membered rings with three nitrogen atoms:
triazine
Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is . They exist in three isomeric forms, 1,3,5-triazines being common.
Structure
The triazines have planar six-membered benzene-like ring but ...
s
* 6-membered rings with five nitrogen atoms:
pentazine
Pentazine is a hypothetical compound that consists of a six-membered aromatic ring containing five nitrogen atoms with the molecular formula C H N5. The name ''pentazine'' is used in the nomenclature of derivatives of this compound.
Pentazine ...
* 6-membered rings with six nitrogen atoms:
hexazine
Hexazine (also known as hexaazabenzene) is a hypothetical allotrope of nitrogen composed of 6 nitrogen atoms arranged in a ring-like structure analogous to that of benzene. It would be the final member of the azabenzene (azine) series, in which al ...
References
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