Everything about Carbon-nitrogen Bond totally explained
A
carbon-nitrogen bond is a
covalent bond between
carbon and
nitrogen and one of the most abundant in
organic chemistry and
biochemistry .
Nitrogen has five
valence electrons and in simple amines it's
trivalent with two remaining electrons forming a
lone pair. Through it, 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 isn't basic due to delocalization of the lone pair into a double bond and in
pyrrole the lone pair is part of an aromatic sextet.
In common with
carbon-carbon bonds, these bonds can be stable
double bonds for instance
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 . The
bond strength in a CN bond is higher (184
kcal/
mol) than that of the CC bond (145 kcal/mol)
[ ]
A CN bond is strongly polarized towards nitrogen (Electronegativity C vs N = 2.55:3.04) and subsequently molecular 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.
Nitrogen functional groups
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