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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. [2]
A triple bond in chemistry is a chemical bond between two atoms involving six bonding electrons instead of the usual two in a covalent single bond. Triple bonds are stronger than the equivalent single bonds or double bonds, with a bond order of three. The most common triple bond is in a nitrogen N 2 molecule; the second most common is that ...
Indeed, in agreement with experiment, carbon-carbon triple bonds are far less reactive with respect to addition reactions than carbon-carbon double bonds as transforming carbon-carbon triple bonds into double bonds also involves the formation of close-pairs of electrons, an energetically costly process. [17] [34]
This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. [1] In inorganic cyanides, the cyanide group is present as the cyanide anion − C≡N. This anion is extremely poisonous. Soluble salts such as sodium cyanide (NaCN) and potassium cyanide (KCN) are highly toxic. [2]
Double, triple, and quadruple bonds are represented by the symbols =, #, and $ respectively as illustrated by the SMILES O=C=O (carbon dioxide CO 2), C#N (hydrogen cyanide HCN) and [Ga+]$[As-] (gallium arsenide). An additional type of bond is a "non-bond", indicated with ., to indicate that two parts are
This is in contrast to carbon-containing compounds which have lower energies of formation for an equivalent number of single or double bonds than for a C≡C triple bond, allowing for the thermodynamically favorable formation of polymers. [9] It is for this reason that the only allotropic form of nitrogen found in nature is molecular nitrogen (N
The less well-characterised ways involve dinitrogen donating electron pairs from the triple bond, either as a bridging ligand to two metal cations (μ, bis-η 2) or to just one (η 2). The fifth and unique method involves triple-coordination as a bridging ligand, donating all three electron pairs from the triple bond (μ 3-N 2).
The bond order itself is the number of electron pairs (covalent bonds) between two atoms. [3] For example, in diatomic nitrogen N≡N, the bond order between the two nitrogen atoms is 3 (triple bond). In acetylene H–C≡C–H, the bond order between the two carbon atoms is also 3, and the C–H bond order is 1 (single bond).