Carbodiimide

In organic chemistry, a carbodiimide (systematic IUPAC name: methanediimine^[1]) is a functional group with the formula RN=C=NR. On Earth they are exclusively synthetic, but in interstellar space the parent compound HN=C=NH has been detected by its maser emissions.^[2]

A well known carbodiimide is dicyclohexylcarbodiimide, which is used in peptide synthesis.^[3] Dialkylcarbodiimides are stable. Some diaryl derivatives tend to convert to dimers and polymers upon standing at room temperature, though this mostly occurs with low melting point carbodiimides that are liquids at room temperature.^[4] Solid diaryl carbodiimides are more stable, but can slowly undergo hydrolysis in the presence of water over time.

^ Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 375. doi:10.1039/9781849733069-00372. ISBN 978-0-85404-182-4. The name carbodiimide, for HN=C=NH, is retained but only for general nomenclature; no substitution of any kind is allowed. The systematic name, methanediimine, is the preferred IUPAC name.
^ McGuire, Brett A.; Loomis, Ryan A.; Charness, Cameron M.; Corby, Joanna F.; Blake, Geoffrey A.; Hollis, Jan M.; Lovas, Frank J.; Jewell, Philip R.; Remijan, Anthony J. (2012-10-20). "Interstellar Carbodiimide (HNCNH): A New Astronomical Detection from the GBT Primos Survey Via Maser Emission Features". The Astrophysical Journal. 758 (2): L33. arXiv:1209.1590. Bibcode:2012ApJ...758L..33M. doi:10.1088/2041-8205/758/2/L33. ISSN 2041-8205. S2CID 26146516.
^ Andrew Williams; Ibrahim T. Ibrahim (1981). "Carbodiimide Chemistry: recent Advances". Chem. Rev. 81 (6): 589–636. doi:10.1021/cr00046a004.
^ Cite error: The named reference Monagle was invoked but never defined (see the help page).

[1] Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 375. doi:10.1039/9781849733069-00372. ISBN 978-0-85404-182-4. The name carbodiimide, for HN=C=NH, is retained but only for general nomenclature; no substitution of any kind is allowed. The systematic name, methanediimine, is the preferred IUPAC name.

[2] McGuire, Brett A.; Loomis, Ryan A.; Charness, Cameron M.; Corby, Joanna F.; Blake, Geoffrey A.; Hollis, Jan M.; Lovas, Frank J.; Jewell, Philip R.; Remijan, Anthony J. (2012-10-20). "Interstellar Carbodiimide (HNCNH): A New Astronomical Detection from the GBT Primos Survey Via Maser Emission Features". The Astrophysical Journal. 758 (2): L33. arXiv:1209.1590. Bibcode:2012ApJ...758L..33M. doi:10.1088/2041-8205/758/2/L33. ISSN 2041-8205. S2CID 26146516.

[Williams-3] Andrew Williams; Ibrahim T. Ibrahim (1981). "Carbodiimide Chemistry: recent Advances". Chem. Rev. 81 (6): 589–636. doi:10.1021/cr00046a004.

[Monagle-4] Cite error: The named reference Monagle was invoked but never defined (see the help page).

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