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Tetrakis(dimethylamino)ethylene (TDAE) is an
TDAE is an electron donor with E = 1.06 V vs Fc+/0. It forms a charge transfer salt with
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula (NMe2)2sub>2 (where Me = CH3). A colorless liquid, this compound is classified as an enamine
An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates.
:
The word "enamine" is derived from the affix ''en''-, used as the suffix of alkene, and th ...
. Primary and secondary enamines tend to isomerize, but tertiary enamines are kinetically stable. 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
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
.
Reactions
TDAE reacts withoxygen
Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...
in a chemiluminescent reaction to give tetramethylurea
Tetramethylurea is the organic compound with the formula (Me2N)2CO. It is a substituted urea. This colorless liquid is used as an aprotic-polar solvent, especially for aromatic compounds and is used e. g. for Grignard reagents.
Production
The s ...
TDAE is an electron donor with E = 1.06 V vs Fc+/0. It forms a charge transfer salt with buckminsterfullerene
Buckminsterfullerene is a type of fullerene with the formula C60. It has a cage-like fused-ring structure (truncated icosahedron) made of twenty hexagons and twelve pentagons, and resembles a soccer ball. Each of its 60 carbon atoms is bonded ...
:
:C2(N(CH3)2)4 + C60 → 2(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,DAE
DAE or Dae may refer to:
As an acronym
* DAE (chemotherapy), a chemotherapy regimen consisting of Daunorubicin, Ara-C (cytarabine) and Etoposide
* Daporijo Airport, the IATA code for an airport in India
* Daxing Airport Express, the airport trans ...
sup>2+ is an alkane with multi-C-N bonds.
References
{{reflist, 30em Dimethylamino compounds Enamines Chemiluminescence