Английская Википедия:Diamine
| Файл:Diamines General Formula V.1.svg General structure of (primary) diamines. The primary amino groups (NH2) are marked blue, R is a divalent organic radical (e.g. a para-phenylene group). |
A diamine is an amine with exactly two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term diamine refers mostly to primary diamines, as those are the most reactive.[1]
In terms of quantities produced, 1,6-diaminohexane (a precursor to Nylon 6-6) is most important, followed by ethylenediamine.[2] Vicinal diamines (1,2-diamines) are a structural motif in many biological compounds and are used as ligands in coordination chemistry.[3]
Aliphatic diamines
Linear
- 1 carbon: methylenediamine (diaminomethane) of theoretical interest only, but its hydrochloride can be used in the synthesis of amides.[4]
- 2 carbons: ethylenediamine (1,2-diaminoethane). Related derivatives include the N-alkylated compounds, 1,1-dimethylethylenediamine, 1,2-dimethylethylenediamine, ethambutol, tetrakis(dimethylamino)ethylene, TMEDA.
-
Ethylenediamine
- 3 carbons: 1,3-diaminopropane (propane-1,3-diamine)
- 4 carbons: putrescine (butane-1,4-diamine)
- 5 carbons: cadaverine (pentane-1,5-diamine)
- 6 carbons: hexamethylenediamine (hexane-1,6-diamine), trimethylhexamethylenediamine
Branched
Derivatives of ethylenediamine are prominent:
- 1,2-diaminopropane, which is chiral.
- diphenylethylenediamine, two diastereomers, one of which is C2-symmetric.
- 1,2-diaminocyclohexane, two diastereomers, one of which is C2-symmetric.
Cyclic
-
1,4-Diazacycloheptane
Xylylenediamines
Xylylenediamines are classified as alkylamines since the amine is not directly attached to an aromatic ring.
- o-xylylenediamine or OXD
- m-xylylenediamine or MXD
- p-xylylenediamine or PXD
Aromatic diamines
Three phenylenediamines are known:[5]
- o-phenylenediamine or OPD
- m-phenylenediamine or MPD
- p-phenylenediamine or PPD. 2,5-diaminotoluene is related to PPD but contains a methyl group on the ring.
-
p-phenylenediamine
Various N-methylated derivatives of the phenylenediamines are known:
- dimethyl-4-phenylenediamine, a reagent.
- N,N'-di-2-butyl-1,4-phenylenediamine, an antioxidant.
Examples with two aromatic rings include derivatives of biphenyl and naphthalene:
References
- ↑ Шаблон:Cite web
- ↑ Шаблон:Cite encyclopedia
- ↑ Lucet, D., Le Gall, T. and Mioskowski, C. (1998), The Chemistry of Vicinal Diamines. Angew. Chem. Int. Ed., 37: 2580–2627. Шаблон:Doi
- ↑ Шаблон:Cite journal
- ↑ Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. Шаблон:Doi
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