Methylene imine

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Methylene imine
Methanimine-2D.png
Methanimine-3D-balls.png
Names
Preferred IUPAC name
Methanimine
Other names
Formaldimine, azomethine, formaldehyde imine
Identifiers
3D model (JSmol)
1900196
ChEBI
ChemSpider
163896
  • InChI=1S/CH3N/c1-2/h2H,1H2
    Key: WDWDWGRYHDPSDS-UHFFFAOYSA-N
  • C=N
Properties
H2C=NH
Molar mass 29.042 g·mol−1
Appearance colorless gas
Related compounds
Related compounds
N-Methylmethanimine
Ethanimine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methylene imine is an organic compound with the formula H2C=NH. The simplest imine, it is a stable, colorless gas that has been detected throughout the universe.[1] Structural parameters determined by microwave spectroscopy include a C=N bond length of 1.27 Å, an N–H bond length of 1.02 Å and an HNC bond angle of 110.5°.[2] Because unhindered imines polymerize or oligomerize when concentrated, methylene imine has not been isolated as a liquid or bulk solid. Attempted synthesis of methylene imine from the reaction of ammonia and formaldehyde produces hexamethylenetetramine.[3]

Synthesis Hexamine.svg

References[edit]

  1. ^ Vuitton, V.; Yelle, R. V.; Anicich, V. G. (2006). "The nitrogen chemistry of Titan's upper atmosphere revealed". Astrophysical Journal. 647: L175–L178. doi:10.1086/507467.
  2. ^ Richard Pearson Jr., Frank J. Lovas (1977). "Microwave spectrum and molecular structure of methylenimine (CH2NH)". J. Chem. Phys. 66: 4149. doi:10.1063/1.434490.
  3. ^ Eller, K.; Henkes, E.; Rossbacher, R.; Höke, H. (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH. doi:10.1002/14356007.a02_001. ISBN 9783527306732.