Dinitrogen tetroxide
chemical compound

Dinitrogen tetroxide, commonly referred to as nitrogen tetroxide (NTO), and occasionally (usually among ex-USSR/Russian rocket engineers) as amyl, is the chemical compound N2O4. It is a useful reagent in chemical synthesis. It forms an equilibrium mixture with nitrogen dioxide. Its molar mass is 92.011 g/mol.
Dinitrogen tetroxide is a powerful oxidizer that is hypergolic (spontaneously ignites) upon contact with various forms of hydrazine, which has made the pair a common bipropellant for rockets.
Structure and properties
Dinitrogen tetroxide could be regarded as two nitro groups (-NO2) bonded together. It forms an equilibrium mixture with nitrogen dioxide. The molecule is planar with an N-N bond distance of 1.78 Å and N-O distances of 1.19 Å. The N-N distance corresponds to a weak bond, since it is significantly longer than the average N-N single bond length of 1.45 Å. This exceptionally weak σ bond (amounting to overlapping of the sp2 hybrid orbitals of the two NO2 units) results from the simultaneous delocalization of the bonding electron pair across the whole N2O4 molecule, and the considerable electrostatic repulsion of the doubly occupied molecular orbitals of each NO2 unit.
Unlike NO2, N2O4 is diamagnetic since it has no unpaired electrons. The liquid is also colorless but can appear as a brownish-yellow liquid due to the presence of NO2 according to the following equilibrium:
N2O4 ⇌ 2 NO2 (ΔH = +57.23 kJ/mol)
Higher temperatures push the equilibrium towards nitrogen dioxide.
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