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A typical double bond consists of one sigma bond and one pi bond; for example, the C=C double bond in ethylene (H 2 C=CH 2). A typical triple bond, for example in acetylene (HC≡CH), consists of one sigma bond and two pi bonds in two mutually perpendicular planes containing the bond axis. Two pi bonds are the maximum that can exist between a ...
The double bond is also stronger, 636 kJ mol −1 versus 368 kJ mol −1 but not twice as much as the pi-bond is weaker than the sigma bond due to less effective pi-overlap. In an alternative representation, the double bond results from two overlapping sp 3 orbitals as in a bent bond .
Pi bonds occur when two orbitals overlap when they are parallel. [9] For example, a bond between two s-orbital electrons is a sigma bond, because two spheres are always coaxial. In terms of bond order, single bonds have one sigma bond, double bonds consist of one sigma bond and one pi bond, and triple bonds contain one sigma bond and two pi bonds.
Linus Pauling proposed that the double bond in ethylene results from two equivalent tetrahedral orbitals from each atom, [5] which later came to be called banana bonds or tau bonds. [6] Erich Hückel proposed a representation of the double bond as a combination of a sigma bond plus a pi bond.
Moreover, the multiple bonds of the elements with n=2 are much stronger than usual, because lone pair repulsion weakens their sigma bonding but not their pi bonding. [2] An example is the rapid polymerization that occurs upon condensation of disulfur, the heavy analogue of O 2. Numerous exceptions to the rule exist. [3]
A carbon–carbon double bond consists of a sigma bond and a pi bond. This double bond is stronger than a single covalent bond (611 kJ/mol for C=C vs. 347 kJ/mol for C–C), [1] but not twice as strong. Double bonds are shorter than single bonds with an average bond length of 1.33 Å (133 pm) vs 1.53 Å for a typical C-C single bond. [7]
When viewed down the bond axis, a σ MO has a circular symmetry, hence resembling a similarly sounding "s" atomic orbital. Typically, a single bond is a sigma bond while a multiple bond is composed of one sigma bond together with pi or other bonds. A double bond has one sigma plus one pi bond, and a triple bond has one sigma plus two pi bonds
An exception is the bond in diboron, which is a pi bond. In contrast, the double bond consists of one sigma bond and one pi bond, and a triple bond consists of one sigma bond and two pi bonds (Moore, Stanitski, and Jurs 396). The number of component bonds is what determines the strength disparity.