| Methyl nitrite | |
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| Identifiers | |
| CAS number | 624-91-9 |
| PubChem | 12231 |
| SMILES |
CON=O
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| Properties | |
| Molecular formula | CH3NO2 |
| Molar mass | 61.04 g mol−1 |
| Melting point |
-16 °C, 257 K, 3 °F |
| Boiling point |
-12 °C, 261 K, 10 °F |
| Hazards | |
| MSDS | External MSDS |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
In organic chemistry, methyl nitrite is the simplest alkyl nitrite.
Contents |
Structure
At room temperature, methyl nitrite exists as a mixture of cis and trans conformers. The cis conformer is 3.13 kJ mol−1 more stable than the trans form, with an energy barrier to rotation of 45.3 kJ mol−1.[1]
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Synthesis
Methyl nitrite can be prepared by the reaction of silver nitrite with a iodomethane: Silver nitrite (AgNO2) exists in solution as the silver ion, Ag+ and the nitrite ion, NO2−. One of the lone pairs on an oxygen from nitrite ion attacks the methyl group (—CH3), releasing the iodide ion into solution.[2] Unlike silver nitrite, silver iodide is highly insoluble in water and thus forms a solid.[3] Note that nitrogen is a better nucleophile than oxygen and most nitrites would react via an SN2-like mechanism and the major product would be nitromethane. For example, sodium and potassium nitrite reacting with iodomethane would produce mostly nitromethane, with methyl nitrite as the minor product. However, the presence of the silver ion in solution has a stabilizing effect on the formation of carbocation intermediates, increasing the percent yield of methyl nitrite. In either case, some nitromethane and methyl nitrite are both formed.[2]
This compound is produced by the combustion of unleaded petrol, and might be a cause of the decline of the House Sparrow in Europe.[4]
See also
References
- ^ B. J. Van der Veken, R. Maas, G. A. Guirgis, H. D. Stidham, T. G. Sheehan, J. R. Durig (1990). J. Phys. Chem. 94 (10): 4029-4039. doi:.
- ^ a b Pavia, Lampman, & Kriz. (2004). Organic Chemistry Volume 2: Organic Chemistry 352. Mason, OH: Cenage Learning.
- ^ Ebbing & Gammon. (2005). General Chemistry (8th ed.). Boston: Houghton Mifflin.
- ^ British Birds, vol 100, September 2007, p558.
External links
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