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A carbon–oxygen bond is a polar covalent bond between atoms of carbon and oxygen. [1] [2] [3]: 16–22 Carbon–oxygen bonds are found in many inorganic compounds such as carbon oxides and oxohalides, carbonates and metal carbonyls, [4] and in organic compounds such as alcohols, ethers, and carbonyl compounds.
Many double bonds exist between two different elements: for example, in a carbonyl group between a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N), and sulfoxides (S=O). In a skeletal formula, a double bond is drawn as two parallel lines (=) between the two connected atoms ...
The polarity of C=O bond also enhances the acidity of any adjacent C-H bonds. Due to the positive charge on carbon and the negative charge on oxygen, carbonyl groups are subject to additions and/or nucleophilic attacks. A variety of nucleophiles attack, breaking the carbon-oxygen double bond, and leading to addition-elimination reactions.
Carbon is the 15th most abundant element in the Earth's crust, and the fourth most abundant element in the universe by mass, after hydrogen, helium, and oxygen. Carbon's widespread abundance, its ability to form stable bonds with numerous other elements, and its unusual ability to form polymers at the temperatures commonly encountered on Earth ...
In non-polar covalent bonds, the electronegativity difference between the bonded atoms is small, typically 0 to 0.3. Bonds within most organic compounds are described as covalent. The figure shows methane (CH 4), in which each hydrogen forms a covalent bond with the carbon. See sigma bonds and pi bonds for LCAO descriptions of such bonding. [22]
Carbon atoms with unsatisfied bonds are found in some oxides, such as the diradical C 2 O or :C=C=O; but these compounds are generally too reactive to be isolated in bulk. [20] Loss or gain of electrons can result in monovalent negative oxygen (-O −), trivalent positive oxygen (≡ O +), or trivalent negative carbon (≡ C −).
Oxygen can form oxides with heavier noble gases xenon and radon, although this needs indirect methods. Even though no oxides of krypton are known, oxygen is able to form covalent bonds with krypton in an unstable compound Kr(OTeF 5) 2. One unexpected oxygen compound is dioxygenyl hexafluoroplatinate, O + 2 PtF −
The bond length between the carbon atom and the oxygen atom is 112.8 pm. [11] [12] This bond length is consistent with a triple bond, as in molecular nitrogen (N 2), which has a similar bond length (109.76 pm) and nearly the same molecular mass. Carbon–oxygen double bonds are significantly longer, 120.8 pm in formaldehyde, for example. [13]