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 sat ...
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 agre ...
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.
...
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 (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, weakl ...
substituents and is of importance as a reagent in
Diels-Alder reactions. It reacts with
norbornadiene 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 pur ...
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 bioc ...
2001, 6, 353–36
Online Article
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, weakl ...
* 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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