Diamine

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 diaminesEdit

LinearEdit

BranchedEdit

Derivatives of ethylenediamine are prominent:

CyclicEdit

XylylenediaminesEdit

Xylylenediamines are classified as alkylamines since the amine is not directly attached to an aromatic ring.

Aromatic diaminesEdit

Three phenylenediamines are known:[4]

Various N-methylated derivatives of the phenylenediamines are known:

Examples with two aromatic rings include derivatives of biphenyl and naphthalene:

ReferencesEdit

  1. ^ "Nucleophilicity Trends of Amines". Master Organic Chemistry. 2018-05-07. Retrieved 2019-08-18.
  2. ^ Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.CS1 maint: uses authors parameter (link)
  3. ^ Lucet, D., Le Gall, T. and Mioskowski, C. (1998), The Chemistry of Vicinal Diamines. Angew. Chem. Int. Ed., 37: 2580–2627. doi: 10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO;2-L
  4. ^ Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_405

External linksEdit