Tetrakis(dimethylamino)ethylene

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Tetrakis(dimethylamino)ethylene
Names
Preferred IUPAC name
N1,N1,N′1,N′1,N2,N2,N′2,N′2-Octamethylethene-1,1,2,2-tetramine
Other names
Octamethyl-ethenetetramine
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.012.398 Edit this at Wikidata
EC Number
  • 213-638-1
UNII
  • InChI=1S/C10H24N4/c1-11(2)9(12(3)4)10(13(5)6)14(7)8/h1-8H3
    Key: CBXRMKZFYQISIV-UHFFFAOYSA-N
  • CN(C)C(=C(N(C)C)N(C)C)N(C)C
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 labelling:
GHS02: FlammableGHS05: Corrosive
Danger
H226, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, 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).

Tetrakis(dimethylamino)ethylene (TDAE) is an organic compound with the formula [C(NMe2)2]2 (where Me = CH3), classified as an enamine. It is a colorless liquid. Primary and secondary enamines tend to isomerize, but tertiary enamines are kinetically stable.[1] The unusual feature of TDAE is that it is a tetra-enamine. The pi-donating tendency of the amine groups strongly modifies the properties of the molecule, which does exhibit properties of a typical alkene.[2]

Reactions

TDAE reacts with oxygen in a chemiluminescent reaction to give tetramethylurea[3][4]

Oxidation of TDAE (chemiluminescence).
Oxidation of TDAE (chemiluminescence).

TDAE is an electron donor with E = 1.06 V vs Fc+/0.[5][6] It forms a charge transfer salt with buckminsterfullerene:[7]

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).[8]

References

  1. ISBN 978-0-471-93623-7
    .
  2. ISBN 9780470771082
    .
  3. doi:10.1021/ja01087a039
    .
  4. ^ "Chemilumineszenz von TDAE" (in German). illumina-chemie.de. 2014-08-08. Retrieved 2016-08-22.
  5. PMID 24273111
    .
  6. PMID 12737575
    .
  7. S2CID 19561675
    .
  8. doi:10.1002/anie.199116781
    .
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