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Hexamethylenediimine

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Hexamethylenediimine
Names
IUPAC name
N-[5-(methylideneamino)pentyl]methanimine
Identifiers
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Properties
C7H16N2
Molar mass 126.2 g/mol
log P 3.6
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Hexamethylenediimine is the organic compound with the formula H2CN(CH2)6NCH2. The molecule is a diimine, consisting of a hexamethylene hydrocarbon chain terminated with imine functional groups. It is the result of the Imine Formation, or Alkylimino-de-oxo-bisubstitution, of Hexamethylenediamine[1]. Hexamethylenediimine can be used to catalyze the polymerization of olefins, and has potential for use in the copolymerization of ethylene and amides[2]. As a diimine, condensation with formaldehyde would ostensibly result in an NHC ligand[3].

File:MolView (structural formula).png
Skeletal formula of hexamethylenediimine
File:MolView (model).png
Ball and stick model of hexamethylenediimine

See Also

Hexamethylenediamine, the related amine.

References

  1. ↑ March, Jerry (1985). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons. ISBN 0-471-85472-7. Search this book on
  2. ↑ Ittel, S. D.; Johnson, L. K.; Brookhart, M. (2000). "Late-Metal Catalysts for Ethylene Homo- and Copolymerization". Chemical Reviews. 100: 1169–1203. doi:10.1021/cr9804644.
  3. ↑ Ison, Elon A.; Ison, Ana (2012). "Synthesis of Well-Defined Copper N-Heterocyclic Carbene Complexes and Their Use as Catalysts for a "Click Reaction": A Multistep Experiment That Emphasizes the Role of Catalysis in Green Chemistry". J. Chem. Educ. 89: 1575–1577. doi:10.1021/ed300243s.

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