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1,8-Diazabicyclo .4.0ndec-7-ene, or more commonly DBU, is a
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
and belongs to the class of amidine
Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2.
Examples of amidines includ ...
compounds. It is used in organic synthesis as a catalyst
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
, a complexing ligand
In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...
, and a non-nucleophilic base
As the name suggests, a non-nucleophilic base is a sterically hindered organic base that is a poor nucleophile. Normal bases are also nucleophiles, but often chemists seek the proton-removing ability of a base without any other functions. Typical ...
.
Occurrence
Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge '' Niphates digitalis''. The biosynthesis of DBU has been proposed to begin with 1,6-hexanedial and 1,3-diaminopropane.
Uses
As a reagent in organic chemistry, DBU is used as a catalyst, a complexing ligand, and a non-nucleophilic base. It is also used as acuring agent
Curing is a chemical process employed in polymer chemistry and process engineering that produces the toughening or hardening of a polymer material by cross-linking of polymer chains. Even if it is strongly associated with the production of thermo ...
for epoxy resins.
It is used in the separation of fullerene
A fullerene is an allotrope of carbon whose molecule consists of carbon atoms connected by single and double bonds so as to form a closed or partially closed mesh, with fused rings of five to seven atoms. The molecule may be a hollow sphere, ...
s in conjunction with trimethylbenzene
The trimethylbenzenes constitute a group of substances of aromatic hydrocarbons, which structure consists of a benzene ring with three methyl groups (–CH3) as a substituent. Through their different arrangement, they form three structural iso ...
. It reacts with C70 and higher fullerenes, but not with to C60
It is also used as a catalyst in the production of polyurethane
Polyurethane (; often abbreviated PUR and PU) refers to a class of polymers composed of organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane is produced from ...
s. It also exhibited its dual character (base and nucleophile) in the synthesis of aryl- and styryl-terminal acetylenes.
See also
* 1,5-Diazabicyclo .3.0on-5-ene *DABCO
DABCO (1,4-diazabicyclo .2.2ctane), also known as triethylenediamine or TEDA, is a bicyclic organic compound with the formula N2(C2H4)3. This colorless solid is a highly nucleophilic tertiary amine base, which is used as a catalyst and reagen ...
References