| 词条 | Hexahydro-1,3,5-triazine |
| 释义 |
In chemistry, hexahydro-1,3,5-triazine is a class of heterocyclic compounds with the formula (CH2NR)3. They are reduced derivatives of 1,3,5-triazine, which have the formula (CHN)3, a family of aromatic heterocycles. PreparationThe parent hexahydro-1,3,5-triazine ((CH2NH)3) has been detected as an intermediate in the condensation of formaldehyde and ammonia, a reaction that affords hexamethylene tetraamine. The N-substituted derivatives are more stable. These N,N',N''-trisubstituted hexahydro-1,3,5-triazines arise from the condensation of the amine 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:[1] 3 RCHO + 3 H2NR → (RCHNH)3 + 3 H2O Known as aldehyde ammonias, these compounds characteristically crystallize with water. 1-Alkanolamines are intermediates in these condensation reactions.[2] {{clear}}The N,N,N-triacyl triazines arise from the reaction of hexamethylene tetraamine with acid chlorides or the condensation of amides with formaldehyde.[3] Unlike the parent triazines, the hexahydro derivatives are conformationally flexible.[4] Trimers of isocyanates are sometimes labeled as 2,4,6-trioxohexahydro-1,3,5-triazines. They have the formula RNC(O))3. The explosive RDX is the trinitro derivative of hexahydro-1,3,5-triazine. Hexahydro-1,3,5-triazine polymers have also been synthesized.[2]References1. ^{{cite journal | last1 = Nielsen | first1 = Arnold T. | last2 = Atkins | first2 = Ronald L. | last3 = Moore | first3 = Donald W. | last4 = Scott | first4 = Robert | last5 = Mallory | first5 = Daniel | last6 = LaBerge | first6 = Jeanne M. | year = 1973 | title = Structure and chemistry of the aldehyde ammonias. 1-Amino-1-alkanols, 2,4,6-trialkyl-1,3,5-hexahydrotriazines, and N,N-dialkylidene-1,1-diaminoalkanes | url = | journal = J. Org. Chem. | volume = 38 | issue = | pages = 3288–3295 | doi = 10.1021/jo00959a010 }} 2. ^1 2 {{Cite journal | doi = 10.1126/science.1251484| pmid = 24833389| title = Recyclable, Strong Thermosets and Organogels via Paraformaldehyde Condensation with Diamines| journal = Science| volume = 344| issue = 6185| pages = 732–5| year = 2014| last1 = Garcia | first1 = J. M.| last2 = Jones | first2 = G. O.| last3 = Virwani | first3 = K.| last4 = McCloskey | first4 = B. D.| last5 = Boday | first5 = D. J.| last6 = Ter Huurne | first6 = G. M.| last7 = Horn | first7 = H. W.| last8 = Coady | first8 = D. J.| last9 = Bintaleb | first9 = A. M.| last10 = Alabdulrahman | first10 = A. M. S.| last11 = Alsewailem | first11 = F.| last12 = Almegren | first12 = H. A. A.| last13 = Hedrick | first13 = J. L.}} 3. ^{{cite journal|author1=Teeters, W. O. |author2=Gradsten, M. A. |title=Hexahydro-1,3,5-tripropionyl-s-triazine|journal=Org. Synth. |year=1950|volume= 30|page= 51|doi=10.15227/orgsyn.030.0051}} 4. ^{{cite journal|doi=10.1021/ja990760d|author=Jewett, J. G., Breeyear, J. J., Brown, J. H., Bushweller, C. H.|title=Stereodynamics of 1,3,5-Trialkyl-1,3,5-triazacyclohexanes: 1H and 13C Dynamic NMR Studies. Solvent Effects. Ab Initio and Molecular Mechanics Calculations|journal= J. Am. Chem. Soc. |year=2000| volume= 122|page= 308}} 2 : Amines|Triazines |
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