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20.4 Amines and Amides | ahaboard
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Amines are molecules that contain carbon-nitrogen bonds. The nitrogen atom in an amine has a lone pair of electrons and three bonds to other atoms, either carbon or hydrogen. Various nomenclatures are used to derive names for amines, but all involve the class-identifying suffix –ine as illustrated here for a few simple examples:
In some amines, the nitrogen atom replaces a carbon atom in an aromatic hydrocarbon. Pyridine (Figure 20.17) is one such heterocyclic amine. A heterocyclic compound contains atoms of two or more different elements in its ring structure.
Figure 20.17The illustration shows one of the resonance structures of pyridine.
Like ammonia, amines are weak bases due to the lone pair of electrons on their nitrogen atoms:
The basicity of an amine’s nitrogen atom plays an important role in much of the compound’s chemistry. Amine functional groups are found in a wide variety of compounds, including natural and synthetic dyes, polymers, vitamins, and medications such as penicillin and codeine. They are also found in many molecules essential to life, such as amino acids, hormones, neurotransmitters, and DNA.
Amides are molecules that contain nitrogen atoms connected to the carbon atom of a carbonyl group. Like amines, various nomenclature rules may be used to name amides, but all include use of the class-specific suffix -amide:
Amides can be produced when carboxylic acids react with amines or ammonia in a process called amidation. A water molecule is eliminated from the reaction, and the amide is formed from the remaining pieces of the carboxylic acid and the amine (note the similarity to formation of an ester from a carboxylic acid and an alcohol discussed in the previous section):
The reaction between amines and carboxylic acids to form amides is biologically important. It is through this reaction that amino acids (molecules containing both amine and carboxylic acid substituents) link together in a polymer to form proteins.
The table here summarizes the structures discussed in this chapter:
Key Concepts and Summary
The addition of nitrogen into an organic framework leads to two families of molecules. Compounds containing a nitrogen atom bonded in a hydrocarbon framework are classified as amines. Compounds that have a nitrogen atom bonded to one side of a carbonyl group are classified as amides. Amines are a basic functional group. Amines and carboxylic acids can combine in a condensation reaction to form amides.
Figure 20.18DNA is an organic molecule and the genetic material for all living organisms. (a) DNA is a double helix consisting of two single DNA strands hydrogen bonded together at each nitrogenous base. (b) This detail shows the hydrogen bonding (dotted lines) between nitrogenous bases on each DNA strand and the way in which each nucleotide is joined to the next, forming a backbone of sugars and phosphate groups along each strand. (c) This detail shows the structure of one of the four nucleotides that makes up the DNA polymer. Each nucleotide consists of a nitrogenous base (a double-ring molecule, in this case), a five-carbon sugar (deoxyribose), and a phosphate group.
Using similarities in sequences, technicians can determine whether a man is the father of a child (the identity of the mother is rarely in doubt, except in the case of an adopted child and a potential birth mother). Likewise, forensic geneticists can determine whether a crime scene sample of human tissue, such as blood or skin cells, contains DNA that matches exactly the DNA of a suspect.
The name alkaloid means “like an alkali.” Thus, an alkaloid reacts with acid. The free compound can be recovered after extraction by reaction with a base:
[R3NH+]Cl−+OH−⟶R3N+H2O+Cl−
The structures of many naturally occurring alkaloids have profound physiological and psychotropic effects in humans. Examples of these drugs include nicotine, morphine, codeine, and heroin. The plant produces these substances, collectively called secondary plant compounds, as chemical defenses against the numerous pests that attempt to feed on the plant:
In these diagrams, as is common in representing structures of large organic compounds, carbon atoms in the rings and the hydrogen atoms bonded to them have been omitted for clarity. The solid wedges indicate bonds that extend out of the page. The dashed wedges indicate bonds that extend into the page. Notice that small changes to a part of the molecule change the properties of morphine, codeine, and heroin. Morphine, a strong narcotic used to relieve pain, contains two hydroxyl functional groups, located at the bottom of the molecule in this structural formula. Changing one of these hydroxyl groups to a methyl ether group forms codeine, a less potent drug used as a local anesthetic. If both hydroxyl groups are converted to esters of acetic acid, the powerfully addictive drug heroin results (Figure 20.19).
Figure 20.19Poppies can be used in the production of opium, a plant latex that contains morphine from which other opiates, such as heroin, can be synthesized. (credit: Karen Roe)
Figure 20.20This condensation reaction forms a dipeptide from two amino acids and leads to the formation of water.
Enzymes are large biological molecules, mostly composed of proteins, which are responsible for the thousands of metabolic processes that occur in living organisms. Enzymes are highly specific catalysts; they speed up the rates of certain reactions. Enzymes function by lowering the activation energy of the reaction they are catalyzing, which can dramatically increase the rate of the reaction. Most reactions catalyzed by enzymes have rates that are millions of times faster than the noncatalyzed version. Like all catalysts, enzymes are not consumed during the reactions that they catalyze. Enzymes do differ from other catalysts in how specific they are for their substrates (the molecules that an enzyme will convert into a different product). Each enzyme is only capable of speeding up one or a few very specific reactions or types of reactions. Since the function of enzymes is so specific, the lack or malfunctioning of an enzyme can lead to serious health consequences. One disease that is the result of an enzyme malfunction is phenylketonuria. In this disease, the enzyme that catalyzes the first step in the degradation of the amino acid phenylalanine is not functional (Figure 20.21). Untreated, this can lead to an accumulation of phenylalanine, which can lead to intellectual disabilities.
Figure 20.21A computer rendering shows the three-dimensional structure of the enzyme phenylalanine hydroxylase. In the disease phenylketonuria, a defect in the shape of phenylalanine hydroxylase causes it to lose its function in breaking down phenylalanine.
Figure 20.23The diagram shows the polymer structure of Kevlar, with hydrogen bonds between polymer chains represented by dotted lines.
Kevlar may be best known as a component of body armor, combat helmets, and face masks. Since the 1980s, the US military has used Kevlar as a component of the PASGT (personal armor system for ground troops) helmet and vest. Kevlar is also used to protect armored fighting vehicles and aircraft carriers. Civilian applications include protective gear for emergency service personnel such as body armor for police officers and heat-resistant clothing for fire fighters. Kevlar based clothing is considerably lighter and thinner than equivalent gear made from other materials (Figure 20.24). Beyond Kevlar, Stephanie Kwolek was instrumental in the development of Nomex, a fireproof material, and was also involved in the creation of Lycra. She became just the fourth woman inducted into the National Inventors Hall of Fame, and received a number of other awards for her significant contributions to science and society.
Figure 20.24(a) These soldiers are sorting through pieces of a Kevlar helmet that helped absorb a grenade blast. Kevlar is also used to make (b) canoes and (c) marine mooring lines. (credit a: modification of work by “Cla68”/Wikimedia Commons; credit b: modification of work by “OakleyOriginals”/Flickr; credit c: modification of work by Casey H. Kyhl)
In addition to its better-known uses, Kevlar is also often used in cryogenics for its very low thermal conductivity (along with its high strength). Kevlar maintains its high strength when cooled to the temperature of liquid nitrogen (–196 °C).
