Acarbon–nitrogen bond is acovalent bond betweencarbon andnitrogen and is one of the most abundant bonds inorganic chemistry andbiochemistry.^[1]

Nitrogen has fivevalence electrons and in simple amines it istrivalent, with the two remaining electrons forming alone pair. Through that pair, nitrogen can form an additional bond tohydrogen making ittetravalent and with a positive charge inammonium salts. Many nitrogen compounds can thus be potentiallybasic but its degree depends on the configuration: the nitrogen atom inamides is not basic due to delocalization of the lone pair into a double bond and inpyrrole the lone pair is part of an aromatic sextet.

Similar tocarbon–carbon bonds, these bonds can form stabledouble bonds, as inimines; andtriple bonds, such asnitriles.Bond lengths range from 147.9pm for simpleamines to 147.5 pm for C-N= compounds such asnitromethane to 135.2 pm for partial double bonds inpyridine to 115.8 pm for triple bonds as innitriles.^[2]

A CN bond is strongly polarized towards nitrogen (theelectronegativities of C and N are 2.55 and 3.04, respectively) and subsequentlymolecular dipole moments can be high:cyanamide 4.27D,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 ofradical molecules which are specifically attracted to the C=N bonds.^[3]

Carbon-nitrogen bond can be analyzed byX-ray photoelectron spectroscopy (XPS). Depending on the bonding states the peak positions differ in N1s XPS spectra.^[4][5][6]

Chemical class	Bond order	Formula	Structural Formula	Example	Avg. C–N bond length (Å)[7]
Amines	1	R3C-NH2		Methylamine	1.469 (neutral amine) 1.499 (ammonium salt)
Aziridines	1	CH2NHCH2		Mitomycin	1.472
Azides	1	R2C-N3		Phenyl azide	1.38–1.48[8] 1.47 (methyl azide)[9] 1.432 (phenyl azide)[10]
Anilines	1	Ph-NH2		Anisidine	1.355 (sp2 N) 1.395 (sp3 N) 1.465 (ammonium salt)
Pyrroles	1			Porphyrin	1.372
Amides	1.2	R-CO-NR2		Acetamide	1.325 (primary) 1.334 (secondary) 1.346 (tertiary)
Pyridines	1.5	pyr		Nicotinamide	1.337
Imines	2	R2C=NR		DBN	1.279 (C=N bond) 1.465 (C–N bond)
Nitriles	3	R-CN		Benzonitrile	1.136
Isonitriles	3	R-NC		TOSMIC	1.154[11]

• Cyanide
• Other carbon bonds withgroup 15 elements:carbon–nitrogen bonds,carbon–phosphorus bonds
• Other carbon bonds withperiod 2 elements:carbon–lithium bonds,carbon–beryllium bonds,carbon–boron bonds,carbon–carbon bonds,carbon–nitrogen bonds,carbon–oxygen bonds,carbon–fluorine bonds
• Carbon–hydrogen bond

• Chemical bonding
• Nitrogen compounds

• Articles with short description
• Short description matches Wikidata