![]() ![]() Due to the positive charge on carbon and the negative charge on oxygen, carbonyl groups are subject to additions and/or nucleophilic attacks. The polarity of C=O bond also enhances the acidity of any adjacent C-H bonds. Δ Hσ values are much higher when the substituents on the carbonyl group are more electronegative than carbon. Substituents can affect carbonyl groups by addition or subtraction of electron density by means of a sigma bond. ![]() Interactions between carbonyl groups and other substituents were found in a study of collagen. A variety of nucleophiles attack, breaking the carbon-oxygen double bond. A qualitative order of electrophilicity is RCHO (aldehydes) > R 2CO (ketones) > RCO 2R' (esters) > RCONH 2 (amides). The carbonyl carbon is typically electrophilic. Inorganic carbonyls have shorter C-O distances: CO, 113 CO 2, 116 and COCl 2, 116 pm. Ī special group of carbonyl compounds are dicarbonyl compounds, which can exhibit special properties.įor organic compounds, the length of the C-O bond does not vary widely from 120 picometers. ![]() Examples of inorganic carbonyl compounds are carbon dioxide and carbonyl sulfide. Other organic carbonyls are urea and the carbamates, the derivatives of acyl chlorides chloroformates and phosgene, carbonate esters, thioesters, lactones, lactams, hydroxamates, and isocyanates. In organic chemistry, a carbonyl group characterizes the following types of compounds: See also: α,β-Unsaturated carbonyl compound ![]()
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