WHAT IS LACTAM ?
before discussing the lactam, I will repeat a bit about the Amide.
Amides
An amide may be produced by combining a carboxylic acid with an amino group. In addition to amide formation, a molecule of water is related. For example, ethyl amine reacts with acetic acid to form ethyl acetamide and water.
CH3CH2-NH2 + HOOC-CH3 → CH3CH2-NH-OC-CH3 + HOH
Notice that, in this instance, two short-chain compounds react to form a longer-chain compound.1The result is called an amide.
Lactams - Cyclic Amides
With some modification, a reaction may be carried out that generates a ring structure containing a similar linkage. Consider the result if two functional groups are a distance apart on the same molecule and react together. Consider, for instance, 4-aminobutyric acid, H2N-CH2CH2CH2-COOH. If reacted utilizing the proper conditions,2
H2N-CH2CH2CH2-COOH → 5-member ring + HOH (see associated image).
The amino group at one end reacts with the carboxylic acid group at the other, closing the molecule to form the ring. The ring structure is called a lactam. The type of lactam is designated by using a Greek letter prefix that indicating the number of carbons in the ring, not counting the carbonyl group. For instance, if there are two such carbons, the prefix is beta (the 2nd letter of the alphabet)-if there are four, the prefix is delta, and so on. The ring formed in the above reaction is a gamma-lactam. It's name is based on the number of carbon atoms in the skeleton-in this instance, butyrolactam. There are other ways of naming the structure, one of which is 2-pyrollidinone.
Reducing the Carbonyl in Lactam to CH2
The carbonyl of a lactam can be reduced to produce a heterocyclic ring. "Heterocyclic" refers to the presence of a non-carbon atom in the ring. It is thus easy to produce a four member ring containing a nitrogen atom, or a five member ring, a six member ring, and so on. Such rings often occur in very important organic compounds related to living things. There are heterocyclic rings in the active ingredients of a plethora of medications. There are a variety of methodologies for reducing the carbonyl. To visualize the end result, again refer to the image associated with this article.
1 Although it isn't obvious as drawn, the carbon-containing chain formed actually consists of six atoms, C-C-C-N-C-C. The oxygen is actually attached to the next-to-last carbon by a double-bond off to the side.
2 Utilizing different conditions can produce a polymeric product. The amino group of one molecule would react with the carboxylic acid of a different molecule, and so on.
one of example from lactams is beta-lactam
how the mechanism of amydes to be cyclic, and then form the lactams?
BalasHapusAn amide may be produced by combining a carboxylic acid with an amino group. In addition to amide formation, a molecule of water is related.
Lactams - Cyclic Amides
With some modification, a reaction may be carried out that generates a ring structure containing a similar linkage. Consider the result if two functional groups are a distance apart on the same molecule and react together. Consider, for instance, 4-aminobutyric acid, H2N-CH2CH2CH2-COOH. If reacted utilizing the proper conditions,2
H2N-CH2CH2CH2-COOH → 5-member ring + HOH (see associated image). The amino group at one end reacts with the carboxylic acid group at the other, closing the molecule to form the ring. The ring structure is called a lactam.