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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. [ 1 ] Nitrogen has five valence electrons and in simple amines it is trivalent , with the two remaining electrons forming a lone pair .
The lone pair repels more strongly than bond pairs; therefore, the bond angle is not 109.5°, as expected for a regular tetrahedral arrangement, but 106.8°. [36] This shape gives the molecule a dipole moment and makes it polar. The molecule's polarity, and especially its ability to form hydrogen bonds, makes
Covalent bonds are also affected by the electronegativity of the connected atoms which determines the chemical polarity of the bond. Two atoms with equal electronegativity will make nonpolar covalent bonds such as H–H. An unequal relationship creates a polar covalent bond such as with H−Cl.
Lewis had suggested in 1916 that two atoms are held together in a chemical bond by sharing a pair of electrons. [18] When each atom contributed one electron to the bond, it was called a covalent bond. When both electrons come from one of the atoms, it was called a dative covalent bond or coordinate bond. The distinction is not very clear-cut.
Molecules, by definition, are most often held together with covalent bonds involving single, double, and/or triple bonds, where a "bond" is a shared pair of electrons (the other method of bonding between atoms is called ionic bonding and involves a positive cation and a negative anion).
The lone electron pair on the nitrogen atom (N) in ammonia, represented as a line above the N, forms a coordinate bond with a proton (H +). After that, all four N−H bonds are equivalent, being polar covalent bonds. The ion has a tetrahedral structure and is isoelectronic with methane and the borohydride anion.
Molecules that are formed primarily from non-polar covalent bonds are often immiscible in water or other polar solvents, but much more soluble in non-polar solvents such as hexane. A polar covalent bond is a covalent bond with a significant ionic character. This means that the two shared electrons are closer to one of the atoms than the other ...
As noted above, covalent and ionic bonds form a continuum between shared and transferred electrons; covalent and weak bonds form a continuum between shared and unshared electrons. In addition, molecules can be polar, or have polar groups, and the resulting regions of positive and negative charge can interact to produce electrostatic bonding ...