chemistry Chemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies the chemical elements that make up matter and chemical compound, compounds made of atoms, molecules a ...

, 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 organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

s with the formula (CH₂NR)₃. Known as aldehyde ammonias, these compounds characteristically crystallize with water. They are reduced derivatives of 1,3,5- triazine, which have the formula (CHN)₃, a family of aromatic heterocycles. They are also called triazacyclohexanes or TACH's, but this acronym is also applied to

cis,cis-1,3,5-triaminocyclohexane ''cis'',''cis''-1,3,5-Triaminocyclohexane is an organic compound with the formula (CH2CHNH2)3. It is a triamine. Of the many isomers possible for triaminocyclohexane, the ''cis'',''cis''-1,3,5-derivative has attracted attention because it is a ...

Preparation

N,N',N''-trisubstituted hexahydro-1,3,5-triazines arise from the condensation of a

primary amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

and formaldehyde as illustrated by the route to 1,3,5-trimethyl-1,3,5-triazacyclohexane: : 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 1- Alkanolamines are intermediates in these condensation reactions. 144px, RDX, an explosive, is a hexahydro-1,3,5-triazine. The parent hexahydro-1,3,5-triazine (CH₂NH)₃ has been detected as an intermediate in the condensation of formaldehyde and ammonia. This reaction affords hexamethylene tetraamine. The N-substituted derivatives are more stable. These 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.

Structure

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 chemical formula, formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a com ...

. 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. Hexahydro-1,3,5-triazine polymers have also been synthesized.

References

{{reflist Amines Triazines