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Carbon–nitrogen bond

Covalent bond

Covalent bond

A carbon–nitrogen bond is a covalent bond between carbon and nitrogen and is one of the most abundant bonds in organic chemistry and biochemistry.

Nitrogen has five valence electrons and in simple amines it is trivalent, with the two remaining electrons forming a lone pair. Through that pair, nitrogen can form an additional bond to hydrogen making it tetravalent and with a positive charge in ammonium salts. Many nitrogen compounds can thus be potentially basic but its degree depends on the configuration: the nitrogen atom in amides is not basic due to delocalization of the lone pair into a double bond and in pyrrole the lone pair is part of an aromatic sextet.

Similar to carbon–carbon bonds, these bonds can form stable double bonds, as in imines; and triple bonds, such as nitriles. Bond lengths range from 147.9 pm for simple amines to 147.5 pm for C-N= compounds such as nitromethane to 135.2 pm for partial double bonds in pyridine to 115.8 pm for triple bonds as in nitriles.

A CN bond is strongly polarized towards nitrogen (the electronegativities of C and N are 2.55 and 3.04, respectively) and subsequently molecular dipole moments can be high: cyanamide 4.27 D, diazomethane 1.5 D, methyl azide 2.17, pyridine 2.19. For this reason many compounds containing CN bonds are water-soluble. N-philes are group of radical molecules which are specifically attracted to the C=N bonds.

Carbon-nitrogen bond can be analyzed by X-ray photoelectron spectroscopy (XPS). Depending on the bonding states the peak positions differ in N1s XPS spectra.

Nitrogen functional groups

Chemical classBond orderFormulaStructural FormulaExampleAvg. C–N bond length (Å)
Amines1R3C-NH2[[File:1°-amino-group.png75pxPrimary amine]][[File:Methylamine-2D.svg75pxmethylamine]]
Methylamine
1.469 (neutral amine)
1.499 (ammonium salt)
Aziridines1CH2NHCH2[[File:Aziridine.png50pxAziridine]][[File:Mitomycin.svg75pxMitomycin]]
Mitomycin
1.472
Azides1R2C-N3[[File:Azide-2D.svg75pxAzide]][[File:Phenyl azide Structural Formula V1.svg75pxPhenyl azide]]
Phenyl azide
title=Azidoacetamide, a neutral small organic azidefirst1=M.last1=Kumasakifirst2=K.last2=Kinbarafirst3=Y.last3=Wadafirst4=M.last4=Araifirst5=M.last5=Tamurajournal=Acta Crystallogr. Eyear=2001volume=57pages=o6–o8doi=10.1107/S160053680001850X}}
1.47 (methyl azide)
1.432 (phenyl azide)
Anilines1Ph-NH2[[File:Aniline.svg50pxAniline]][[File:O-Anisidine-Structural Formula V.1.svg75pxAnsidine]]
Anisidine1.355 (sp2 N)
1.395 (sp3 N)
1.465 (ammonium salt)
Pyrroles1[[File:Pyrrol2.svg75pxamide]][[File:Porphyrin.svg75pxPorphyrin]]
Porphyrin1.372
Amides1.2R-CO-NR2[[File:Amide-(tertiary).svg75pxamide]][[File:Acetamide skeletal.svg75pxAcetamide]]
Acetamide1.325 (primary)
1.334 (secondary)
1.346 (tertiary)
Pyridines1.5pyr[[File:Pyridine.svg75pxpyridine]][[File:Nicotinamide structure.svg75pxNicotinamide]]
Nicotinamide1.337
Imines2R2C=NR[[File:Imine general structure B.svg75pximine]][[File:DBN.png75pxDBN]]
DBN1.279 (C=N bond)
1.465 (C–N bond)
Nitriles3R-CN[[File:Nitril (vzorec).svg70pxNitrile]][[File:Benzonitrile.svg75pxBenzonitrile]]
Benzonitrile1.136
Isonitriles3R-NC[[File:Isocyanide-2D.png70pxisonitrile]][[File:TosMIC-2D-skeletal.png75pxTOSMIC]]
TOSMIC1.154

References

References

  1. ''Organic Chemistry'' John McMurry 2nd Ed.
  2. [[CRC Handbook of Chemistry and Physics]] 65Th Ed.
  3. (2002). "5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine". Chemical Communications.
  4. (2021-07-12). "Origins of peaks of graphitic and pyrrolic nitrogen in N1s X-ray photoelectron spectra of carbon materials: quaternary nitrogen, tertiary amine, or secondary amine?". Journal of Materials Science.
  5. (2014-04-01). "Nitrogen-containing graphene analyzed by X-ray photoelectron spectroscopy". Carbon.
  6. (2021-09-01). "Unveiling Bonding States and Roles of Edges in Nitrogen-Doped Graphene Nanoribbon by X-ray Photoelectron Spectroscopy". Carbon.
  7. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen. Tables of bond Lengths determined by X-Ray and Neutron Diffraction. Part 1. Bond Lengths in Organic Compounds. ''J. Chem. Soc. Perkin Trans. II'' '''1987''', S1-S19.
  8. (2001). "Azidoacetamide, a neutral small organic azide". [[Acta Crystallographica.
  9. (1960). "An Electron Diffraction Investigation of the Molecular Structure of Methyl Azide". [[Journal of Physical Chemistry.
  10. (2009). "Controllable Selective Functionalization of a Cavitand via Solid State Photolysis of an Encapsulated Phenyl Azide". [[Organic Letters.
  11. (2015). "Crystal structure of ''p''-toluenesulfonylmethyl isocyanide". [[Acta Crystallographica.
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