Table of Contents
Carbonyl Group Definition
Within a larger carbon-based molecule, a carbonyl group is a functional group defined by a carbon atom doubly connected to an oxygen. Oxygen creates a resonance hybrid structure during which electrons are continuously redistributed thanks to its electronegativity. As a result, the molecule can participate in a greater number of activities.
What is Carbonyl Group?
The difference in electronegativity between carbon and oxygen gives a group its strength. Because oxygen is more electronegative than carbon, it tends to draw electrons away from it. As a result, the carbon in the molecule has more area for electrons from other atoms.
This permits the entire molecule to take on a variety of distinct configurations, which are referred to as resonance hybrid structures. The resonant structures of the molecule can interact with a broad range of other molecules present when the molecule interacts with the vast array of other molecules in its environment.
A mostly-carbon molecule could not interact with as many other molecules without the disturbance of the electron structure produced by a carbonyl group. A carbonyl group in a molecule permits it to undertake the many processes required for life to exist.
A carbonyl group is found in many common biological compounds, allowing the organism to make new molecules and alter them with a variety of functional groups.
Carbonyl Group Structure
The picture below shows a carbonyl group, with R and R’ indicating additional carbons in a longer chain to which the core carbonyl group is connected. As seen in the figure below, the carbonyl group can be linked to several carbons. Single atoms can bind to a carbonyl group, as in the case of carbon dioxide.
While this is a very basic structure, it can result in a variety of chemical reactions. This is primarily owing to the oxygen atom’s proclivity for hording electrons within bonds. This produces a polarised point that can interact with a variety of different atoms and molecules.
Carbonyl Group Function
i. Destabilizing Bonds Within a Molecule
The carbonyl group’s main purpose is to destabilise the bonds in the carbon chain. Within the carbonyl group, the electronegative oxygen atom attracts more electrons than the carbon it is linked to. As a result, the carbon inside the carbonyl group will become more positive as the negative electrons that are attracted toward the oxygen lose their electrical effect.
Because the carbon contains a small positive charge, it is now known as a carbocation. As a result of the shift in electron distribution caused by the slightly positive charge on the carbonyl group’s carbon, a wide range of reactions are possible.
ii. Carbonyl Group as an Electron Sink
The impact of the oxygen atom and the ensuing carbocation can stabilise the development of a carbanion intermediate in one of the neighbouring carbons, in addition to producing a somewhat positive carbocation inside the carbonyl group.
Informally, the carbonyl group is known as an electron sink because it may “soak up” additional electrons in the molecule. These additional electrons will travel between the carbon atoms and the oxygen atoms, forming double bonds that will fade to more electrically negative and positive regions.
A variety of significant responses are possible as a result of this instability. The formation of nucleophiles and electrophiles with carbonyl groups is that the start line for several processes that produce carbon-carbon bonds.
As the electrophile, the carbonyl group’s carbon may absorb electrons to form carbon-carbon bonds, while the nucleophile, a carbanion intermediate (formed by another carbonyl group), can give electrons.
iii. Utilization Through Catalysts
Biochemical reactions in organisms modify the activity of the carbonyl group by reacting with metals and acids in the environment. The oxygen will react with various acids and metals, decreasing its electronegativity. As a result, the oxygen will remove less electrons from the carbon molecule to which it is bonded.
This promotes the creation of new carbon-carbon bonds by favouring the development of the negative carbanion intermediate rather than a carbon-carbon double bond. Similarly, imine groups delocalize negative charges on carbons in a similar way and can enable comparable reactions.
Common Chemicals with Carbonyl Group
As a result of the shift in electron distribution caused by the slightly positive charge on the carbonyl group’s carbon, a wide range of reactions are possible. The carbonyl group is found at the conclusion of a sequence of bound carbons in aldehydes.
The carbonyl group of ketones, on the other hand, is in the midst of many linked carbon atoms. Because of this variation, the bonding conditions inside the molecules are very varied, affecting how they interact with other substances. Furthermore, carboxylic acid is a frequent component in the production of amino acids.
This molecule has a carbonyl group immediately linked to a hydroxide group, allowing it to make proteins. The carbonyl group sets up the circumstances for the hydroxide group to be replaced by a bond to another amino acids N terminus.
The two amino acids form a covalent connection that is extremely difficult to break. Carbon dioxide, which is essentially a carbonyl group with an oxygen atom replaced, is most likely the simplest carbonyl group. This molecule may be a byproduct of respiration and plays a crucial role within the carbon cycle.
Carbonyl Group Citations
- Use of carbonyl group addition–elimination reactions for synthesis of nucleic acid conjugates. Bioconjug Chem . May-Jun 2005;16(3):471-89.
- The significance of the 20-carbonyl group of progesterone in steroid receptor binding: a molecular dynamics and structure-based ligand design study. Steroids . 2003 Nov;68(10-13):869-78.
- Functionalization of the carbonyl group in position 6 of morphinan-6-ones. Development of novel 6-amino and 6-guanidino substituted 14-alkoxymorphinans. Curr Pharm Des . 2013;19(42):7391-9.
- Acid-Base Free Main Group Carbonyl Analogues. Angew Chem Int Ed Engl . 2021 Apr 12;60(16):8626-8648.