Tetrakis(dimethylamino)ethylene
Chemical compound From Wikipedia, the free encyclopedia
Tetrakis(dimethylamino)ethylene (TDAE) is an organic compound with the formula ((CH3)2N)2C=C(N(CH3)2)2, It is a colorless liquid. It is classified as an enamine. Primary and secondary enamines tend to isomerize, but tertiary enamines are kinetically stable.[1] One unusual feature of TDAE is that it is a tetra-enamine. The pi-donating tendency of the amine groups strongly enhances the basicity of the molecule, which does exhibit properties of a typical alkene.[2]
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| Names | |||
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| 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 TDAE | |||
| Identifiers | |||
3D model (JSmol) |
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| ChemSpider | |||
| ECHA InfoCard | 100.012.398 | ||
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PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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| 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: | |||
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| 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).
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Reactions
TDAE reacts with oxygen in a chemiluminescent reaction to give tetramethylurea.[3][4] The initial intermediate is (2+2) adduct, a 1,2-dioxetane. This species decomposes to electronically excited tetramethylurea. This returns to the ground state is accompanied by emission of green light with a maximum at 515 nm.[5]
TDAE is an electron donor with E = 1.06 V vs Fc+/0.[6]
TDAE has been examined as a reductant in coupling reactions.[7]
As one of many of examples of its redox behavior forms a charge-transfer salt with buckminsterfullerene:[8]
- 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.[9]
Synthesis
It is available by pyrolysis of tris(dimethylamino)methane by pyrolysis[10] or from chlorotrifluoroethene and dimethylamine.[11]
References
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