Hexahydro-1,3,5-triazine on:
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'' -trisubstituted hexahydro-1,3,5-triazines arise from the condensation of the 
The N,N',N"-triacyltriazines are trizines with acyl groups attached to the three nitrogen centers of the ring. These triacyltriazines arise from the reaction of hexamethylene tetraamine with acid chlorides or the condensation of amides with formaldehyde.
Unlike the parent triazines, the hexahydro derivatives are conformationally flexible.
Trimers of
In chemistry
Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions ...
, hexahydro-1,3,5-triazine is a class of heterocyclic compound
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 ...
s with the formula (CH2NR)3. They are reduced derivatives of 1,3,5-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 ...
, which have the formula (CHN)3, a family of aromatic heterocycles. They are often called triazacyclohexanes or TACH's but this acronym is also applied to cis,cis-1,3,5-triaminocyclohexane.
Preparation
The parent hexahydro-1,3,5-triazine ((CH2NH)3) has been detected as an intermediate in the condensation of formaldehyde and ammonia, a reaction that affordshexamethylene tetraamine
Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin, is a heterocyclic organic compound with the formula (CH2)6N4. This white crystalline compound is highly soluble in water and polar organic solvents. It has a cage-like s ...
. The N-substituted derivatives are more stable. These N,N',Namine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...
and formaldehyde as illustrated by the route to 1,3,5-trimethyl-1,3,5-triazacyclohexane
1,3,5-Trimethyl-1,3,5-triazacyclohexane is an organic compound with the formula (CHNCH). It is a colorless liquid that is soluble in many organic solvents. Structurally, it is one of several related hexahydro-1,3,5-triazines, which typically re ...
:
: 3 CH2O + 3 H2NMe → (CH2NMe)3 + 3 H2O
The C-substituted derivatives are obtained by reaction of aldehydes and ammonia:
:3 RCHO + 3 NH3 → (RCHNH)3 + 3 H2O
Known as aldehyde ammonias, these compounds characteristically crystallize with water. 1-Alkanolamine
In organic chemistry, alkanolamines are organic compounds that contain both hydroxyl () and amino (, , and ) functional groups on an alkane backbone. The term alkanolamine is a broad class term that is sometimes used as a subclassification.
...
s are intermediates in these condensation reactions.
144px, RDX, an explosive, is a hexahydro-1,3,5-triazine.
The N,N',N"-triacyltriazines are trizines with acyl groups attached to the three nitrogen centers of the ring. These triacyltriazines arise from the reaction of hexamethylene tetraamine with acid chlorides or the condensation of amides with formaldehyde.
Unlike the parent triazines, the hexahydro derivatives are conformationally flexible.
Related compounds and derivatives
Trimers of isocyanate
In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyan ...
s are sometimes labeled as 2,4,6-trioxohexahydro-1,3,5-triazines. They have the formula (RNC(O))3 and based on the isocyanuric (trione) tautomer of cyanuric acid
Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a component of bleach ...
.
The N,N',N"-hexahydro-1,3,5-triazines function as tridentate ligands, which are called TACH (triazacyclohexanes). Examples include Mo(CO)3 CH2)3(NMe)3formed from the TACH ligand and molybdenum hexacarbonyl
Molybdenum hexacarbonyl (also called molybdenum carbonyl) is the chemical compound with the formula Mo(CO)6. This colorless solid, like its chromium and tungsten analogues, is noteworthy as a volatile, air-stable derivative of a metal in its zero ...
.
Hexahydro-1,3,5-triazine polymers have also been synthesized.
References
{{reflist Amines Triazines