A carbon–nitrogen bond is a
covalent bond
A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atom ...
between
carbon
Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
and
nitrogen
Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...
and is one of the most abundant bonds in
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...
and
biochemistry
Biochemistry, or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology, a ...
.
Nitrogen has five
valence electrons and in simple amines it is
trivalent, with the two remaining electrons forming a
lone pair
In chemistry, a lone pair refers to a pair of valence electrons that are not shared with another atom in a covalent bondIUPAC ''Gold Book'' definition''lone (electron) pair''/ref> and is sometimes called an unshared pair or non-bonding pair. Lone ...
. Through that pair, nitrogen can form an additional bond to
hydrogen
Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...
making it
tetravalent and with a positive charge in
ammonium salts. Many nitrogen compounds can thus be potentially
basic
Basic or BASIC may refer to:
Science and technology
* BASIC, a computer programming language
* Basic (chemistry), having the properties of a base
* Basic access authentication, in HTTP
Entertainment
* Basic (film), ''Basic'' (film), a 2003 film
...
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 length
In molecular geometry, bond length or bond distance is defined as the average distance between Atomic nucleus, nuclei of two chemical bond, bonded atoms in a molecule. It is a Transferability (chemistry), transferable property of a bond between at ...
s range from 147.9
pm for simple
amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
s 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.
[ CRC Handbook of Chemistry and Physics 65Th Ed.]
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
Diazomethane is an organic chemical compound with the formula CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow ga ...
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
See also
*
Cyanide
* Other carbon bonds with
group 15 elements: carbon–nitrogen bonds,
carbon–phosphorus bonds
* Other carbon bonds with
period 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
References
{{DEFAULTSORT:Carbon-nitrogen bond
Chemical bonding
Nitrogen compounds