|Preferred IUPAC name|
| Other names
Borazole (after the German name for benzene, benzol)
|3D model (Jmol)||Interactive image|
|Molar mass||80.50 g/mol|
|Melting point||−58 °C (−72 °F; 215 K)|
|Boiling point||53 °C (127 °F; 326 K) (55 °C at 105 Pa)|
Point Group= D3h
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|(what is ?)|
Borazine is an inorganic compound with the chemical formula (BH)3(NH)3. In this cyclic compound, the three BH units and three NH units alternate. The compound is isoelectronic and isostructural with benzene. Like benzene, borazine is a colourless liquid. For this reason borazine is sometimes referred to as "inorganic benzene".
- 3 B2H6 + 6 NH3 → 2 B3H6N3 + 12 H2
- 3 LiBH4 + 3 NH4Cl → B3H6N3 + 3 LiCl + 9 H2
In a two-step process to borazine, boron trichloride is first converted to trichloroborazine:
- 3 BCl3 + 3 NH4Cl → Cl3B3H3N3 + 9 HCl
The B-Cl bonds are subsequently converted to B-H bonds:
- 2 Cl3B3H3N3 + 6 NaBH4 → 2 B3H6N3 + 3 B2H6 + 6 NaCl
Borazine is a colourless liquid with an aromatic smell. In water it hydrolyzes to boric acid, ammonia, and hydrogen. Borazine, with a standard enthalpy change of formation ΔHf of −531 kJ/mol, is thermally very stable.
Structure and bonding
Borazine is isostructural with benzene. The six B-N bonds have length of 1.436 Å. The carbon–carbon bond in benzene is shorter length at 1.397 Å. The boron–nitrogen bond length is between that of the boron–nitrogen single bond with 0.151 nm and the boron–nitrogen double bond which is 0.131 nm. This suggests partial delocalisation of nitrogen lone-pair electrons.
The electronegativity of boron (2.04 on the Pauling scale) compared to that of nitrogen (3.04) and also the electron deficiency on the boron atom and the lone pair on nitrogen favor alternative mesomer structures for borazine.
- B3N3H6 + 3 HCl → B3N3H9Cl3
- Addition reaction of borazine with hydrogen chloride
- B3N3H9Cl3 + NaBH4 → (BH4N)3
- reduction with sodium borohydride
The addition reaction with bromine does not require a catalyst. Borazines undergo nucleophilic attack at boron and electrophilic attack at nitrogen. Heating borazine at 70 °C expels hydrogen with formation of a borazinyl polymer or polyborazylene, in which the monomer units are coupled in a para fashion by new boron-nitrogen bonds. Boron nitride can be prepared by heating polyborazylene to 1000 °C. Borazines are also starting materials for other potential ceramics such as boron carbonitrides. Borazine can also be used as a precursor to grow boron nitride thin films on surfaces, such as the nanomesh structure which is formed on rhodium.
Polyborazylene has been proposed as a recycled hydrogen storage medium for hydrogen fuel cell vehicle applications, using a "single pot" process for digestion and reduction to recreate ammonia borane.
Among other B-N type compounds mixed amino-nitro substituted borazines have been predicted to outperform carbon based explosives such as CL-20.
|Wikimedia Commons has media related to borazine.|
- 1,2-dihydro-1,2-azaborine — an aromatic chemical compound with properties intermediate between benzene and borazine.
- Carborazine - another six membered aromatic ring with two carbons, two nitrogens and two borons in opposing pairs.
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