Tetrakis(dimethylamino)ethylene

Tetrakis(dimethylamino)ethylene (TDAE) is an organic compound with the formula C2(N(CH3)2)4. It is a colorless liquid. It is classified as an enamine.[1]

Tetrakis(dimethylamino)ethylene
Names
IUPAC name
1-N,1-N,1-N',1-N',2-N,2-N,2-N',2-N'-octamethylethene-1,1,2,2-tetramine
Other names
Octamethyl-ethenetetramine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.398
EC Number
  • 213-638-1
UNII
Properties
C10H24N4
Molar mass 200.330 g·mol−1
Appearance colorless liquid
Density 0.861 g/cm3 (25 °C)
Melting point −4 °C (25 °F; 269 K)
Boiling point 59 °C (0.9 mm Hg)
Hazards
GHS pictograms
GHS Signal word Danger
H226, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P370+378, P403+235, P405, P501
Flash point 53 °C (127 °F; 326 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Reactions

TDAE reacts with oxygen in a chemiluminscent reaction to give tetramethylurea[2][3]

Oxidation of TDAE (chemiluminescence).

TDAE is an electron donor with E = 1.06 v vs Fc+/0.[4] It forms a charge transfer salt with buckminsterfullerene:[5]

C2(N(CH3)2)4 + C60 → [C2(N(CH3)2)4+][C60]

Oxidation affords a dication.

Structure

Crystallographic analysis show that TDAE is a highly distorted alkene, the dihedral angle for the two N2C termini is 28″. The C=C distance is alkene-like, 135 pm. The nearly isostructural tetraisopropylethylene also has a C=C distance of 135 pm, but its C6 core is planar. In contrast, [TDAE]2+ is an alkane with multi-C-N bonds.

Structure of TDAE and its dication (distances in picometers).[6]

References

  1. David M. Lemal (1968). "Tetraaminoethylenes". In Saul Patai (ed.). The Amino Group. pp. 701–748. doi:10.1002/9780470771082. ISBN 9780470771082.
  2. H.E. Winberg; J. R. Downing; D. D. Coffman (1965). "The Chemiluminescence of Tetrakis(dimethylamino)ethylene". J. Am. Chem. Soc. 87 (9): 2054–2055. doi:10.1021/ja01087a039.
  3. "Chemilumineszenz von TDAE" (in German). illumina-chemie.de. 2014-08-08. Retrieved 2016-08-22.
  4. Kuroboshi, Manabu; Waki, Yoko; Tanaka, Hideo (2003). "Palladium-Catalyzed Tetrakis(dimethylamino)ethylene-Promoted Reductive Coupling of Aryl Halides". The Journal of Organic Chemistry. 68 (10): 3938–3942. doi:10.1021/jo0207473. PMID 12737575.
  5. Allemand PM, Khemani KC, Koch A, et al. (1991). "Organic Molecular Soft Ferromagnetism in a Fullerene". Science. 253 (5017): 301–302. Bibcode:1991Sci...253..301A. doi:10.1126/science.253.5017.301. PMID 17794696. S2CID 19561675.
  6. Bock, Hans; Borrmann, Horst; Havlas, Zdenek; et al. (1991). "Tetrakis(dimethylamino)ethene: An Extremely Electron-Rich Molecule with Unusual Structure both in the Crystal and in the Gas Phase". Angewandte Chemie International Edition in English. 30 (12): 1678–1681. doi:10.1002/anie.199116781.
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