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With 133 pm, the ethylene C=C bond length is shorter than the C−C length in ethane with 154 pm. 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.
Comparison of bond lengths in simple hydrocarbons [5] Molecule Ethane: Ethylene: Acetylene: Formula C 2 H 6: C 2 H 4: C 2 H 2: Class alkane: alkene: alkyne: Structure Hybridisation of carbon sp 3: sp 2: sp C-C bond length 153.5 pm: 133.9 pm: 120.3 pm: Proportion of C-C single bond 100% 87% 78% Structure determination method microwave ...
Shorter than average C–C bond distances are also possible: alkenes and alkynes have bond lengths of respectively 133 and 120 pm due to increased s-character of the sigma bond. In benzene all bonds have the same length: 139 pm. Carbon–carbon single bonds increased s-character is also notable in the central bond of diacetylene (137 pm) and ...
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]
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]
Molecular geometries can be specified in terms of 'bond lengths', 'bond angles' and 'torsional angles'. The bond length is defined to be the average distance between the nuclei of two atoms bonded together in any given molecule. A bond angle is the angle formed between three atoms across at least two bonds.
The average length of a C–C single bond is 154 pm; that of a C=C double bond is 133 pm. In localized cyclohexatriene, the carbon–carbon bonds should be alternating 154 and 133 pm. Instead, all carbon–carbon bonds in benzene are found to be about 139 pm, a bond length intermediate between single and double bond.
The C–O bond is polarized towards oxygen (electronegativity of C vs O, 2.55 vs 3.44). Bond lengths [4] for paraffinic C–O bonds are in the range of 143 pm – less than those of C–N or C–C bonds. Shortened single bonds are found with carboxylic acids (136 pm) due to partial double bond character and elongated bonds are found in epoxides ...