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The bond lengths of these so-called "pancake bonds" [6] are up to 305 pm. 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.
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 ...
Length of a typical covalent bond (C–C) 280 pm Average size of the water molecule (actual lengths may vary) 500 pm Width of protein α helix: 10 −9: 1 nanometer 1 nm Diameter of a carbon nanotube [12] Diameter of smallest transistor gate (as of 2016) [13] 2 nm Diameter of the DNA helix [14] 2.5 nm
In solid materials, the atomic spacing is described by the bond lengths of its atoms. In ordered solids, the atomic spacing between two bonded atoms is generally around a few ångströms (Å), which is on the order of 10 −10 meters (see Lattice constant ).
C═C acyclic C═C monosub. alkenes 1645 medium 1,1-disub. alkenes 1655 medium cis-1,2-disub. alkenes 1660 medium trans-1,2-disub. alkenes 1675 medium trisub., tetrasub. alkenes 1670 weak conjugated C═C dienes 1600 strong 1650 strong with benzene ring 1625 strong with C═O 1600 strong C═C (both sp 2) any 1640–1680 medium aromatic C═C any
An alkane has only C–H and C–C single bonds. The former result from the overlap of an sp 3 orbital of carbon with the 1s orbital of a hydrogen; the latter by the overlap of two sp 3 orbitals on adjacent carbon atoms. The bond lengths amount to 1.09 × 10 −10 m for a C–H bond and 1.54 × 10 −10 m for a C–C bond.
Both of these effects tend to reduce the carbon-carbon bond order, leading to an elongated C−C distance and a lowering of its vibrational frequency. In Zeise's salt K[PtCl 3 (C 2 H 4)]. H 2 O the C−C bond length has increased to 134 picometres from 133 pm for ethylene. In the nickel compound Ni(C 2 H 4)(PPh 3) 2 the value is 143 pm.
By contrast, the C-C bond lengths in cyclopropane are 151 pm. The C=O bond length of 119 pm is short compared to the 123 pm bond length in acetone. [1] The value of ν C=O in the infrared spectrum is near 1815 cm −1, ca. 70 cm −1 higher than values for a typical ketone.