Amide in the context of Dipolar compound


Amide in the context of Dipolar compound

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⭐ Core Definition: Amide

In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R″, where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, as in asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid (R−C(=O)−OH) with the hydroxyl group (−OH) replaced by an amino group (−NR′R″); or, equivalently, an acyl (alkanoyl) group (R−C(=O)−) joined to an amino group.

Common amides are formamide (H−C(=O)−NH2), acetamide (H3C−C(=O)−NH2), benzamide (C6H5−C(=O)−NH2), and dimethylformamide (H−C(=O)−N(−CH3)2).

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Amide in the context of Urea

Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula CO(NH2)2. This amide has two amino groups (−NH2) joined by a carbonyl functional group (−C(=O)−). It is thus the simplest amide of carbamic acid.

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Amide in the context of Chitin

Chitin (C8H13O5N)n (/ˈktɪn/ KY-tin) is a long-chain polymer of N-acetylglucosamine, an amide derivative of glucose. Chitin is the second most abundant polysaccharide in nature (behind only cellulose); an estimated 1 billion tons of chitin are produced each year in the biosphere. It is a primary component of cell walls in fungi (especially filamentous and mushroom-forming fungi), the exoskeletons of arthropods such as crustaceans and insects, the radulae, cephalopod beaks and gladii of molluscs and in some nematodes and diatoms.It is also synthesised by at least some fish and lissamphibians. Commercially, chitin is extracted from the shells of crabs, shrimps, shellfish and lobsters, which are major by-products of the seafood industry. The structure of chitin is comparable to cellulose, forming crystalline nanofibrils or whiskers. It is functionally comparable to the protein keratin. Chitin has proved useful for several medicinal, industrial and biotechnological purposes.

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Amide in the context of Nylon

Nylon is a family of synthetic polymers characterized by amide linkages, typically connecting aliphatic or semi-aromatic groups.

Nylons are generally brownish in color and can possess a soft texture, with some varieties exhibiting a silk-like appearance. As thermoplastics, nylons can be melt-processed into fibers, films, and diverse shapes. The properties of nylons are often modified by blending with a variety of additives.

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Amide in the context of Formamide

Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticides, and in the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers. Some astrobiologists suggest that it may be an alternative to water as the main solvent in other forms of life.

Formamides are compounds of the type RR′NCHO. One important formamide is dimethylformamide, (CH3)2NCHO.

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Amide in the context of Peptide bond

In organic chemistry, a peptide bond is an amide type of covalent chemical bond linking two consecutive alpha-amino acids from C1 (carbon number one) of one alpha-amino acid and N2 (nitrogen number two) of another, along a peptide or protein chain.

It can also be called a eupeptide bond to distinguish it from an isopeptide bond, which is another type of amide bond between two amino acids.

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Amide in the context of Pyrrolysine

Pyrrolysine (symbol Pyl or O), encoded by the "amber" stop codon UAG, is a proteinogenic amino acid that is used in some methanogenic archaea and in bacteria. It consists of lysine with a 4-methylpyrroline-5-carboxylate in amide linkage with the N of the lysine. Its pyrroline side-chain is similar to that of lysine in being basic and positively charged at neutral pH.

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Amide in the context of Acyl

In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an organyl group (R−C=O) or hydrogen in the case of formyl group (H−C=O). In organic chemistry, the acyl group (IUPAC name alkanoyl if the organyl group is alkyl) is usually derived from a carboxylic acid, in which case it has the formula R−C(=O)−, where R represents an organyl group or hydrogen. Although the term is almost always applied to organic compounds, acyl groups can in principle be derived from other types of acids such as sulfonic acids and phosphonic acids. In the most common arrangement, acyl groups are attached to a larger molecular fragment, in which case the carbon and oxygen atoms are linked by a double bond.

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Amide in the context of Polyamide

A polyamide is a polymer with repeating units linked by amide bonds.

Polyamides occur both naturally and artificially. Examples of naturally occurring polyamides are proteins, such as wool and silk. Artificially made polyamides can be made through step-growth polymerization or solid-phase synthesis yielding materials such as nylons, aramids, and sodium polyaspartate. Synthetic polyamides are commonly used in textiles, automotive industry, carpets, kitchen utensils and sportswear due to their high durability and strength. The transportation manufacturing industry is the major consumer, accounting for 35% of polyamide (PA) consumption.

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Amide in the context of Carbamic acid

Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula H2NCOOH. It can be obtained by the reaction of ammonia NH3 and carbon dioxide CO2 at very low temperatures, which also yields ammonium carbamate [NH4][NH2CO2]. The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH.

Carbamic acid could be seen as both an amine and carboxylic acid, and therefore an amino acid; however, the attachment of the carboxyl group –COOH directly to the nitrogen atom (without any intermediate carbon chain) makes it behave very differently from the amino acids with intermediate carbon chain. (Glycine NH2CH2COOH is generally considered to be the simplest amino acid.) The hydroxyl group –OH attached to the carbon also excludes it from the amide class.

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Amide in the context of Capsaicin

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) (/kæpˈs.ə.sɪn/, commonly /kæpˈssɪn/) is a chemical compound that is the main active component of chili peppers and gives them their "spicy" or "hot" taste. It is a potent irritant for mammals, including humans, for which it produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, likely as deterrents against eating by mammals and against the growth of fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent (i.e., spicy) crystalline solid.

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Amide in the context of Glutamine

Glutamine (symbol Gln or Q) is an α-amino acid that is used in the biosynthesis of proteins. Its side chain is similar to that of glutamic acid, except the carboxylic acid group is replaced by an amide. It is classified as a charge-neutral, polar amino acid. It is non-essential and conditionally essential in humans, meaning the body can usually synthesize sufficient amounts of it, but in some instances of stress, the body's demand for glutamine increases, and glutamine must be obtained from the diet. It is encoded by the codons CAA and CAG. It is named after glutamic acid, which in turn is named after its discovery in cereal proteins, gluten.

In human blood, glutamine is the most abundant free amino acid.

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Amide in the context of N-Acetylglucosamine

N-Acetylglucosamine (GlcNAc) is an amide derivative of the monosaccharide glucose. It is a secondary amide between glucosamine and acetic acid. It is significant in several biological systems.

It is part of a biopolymer in the bacterial cell wall, which is built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. This layered structure is called peptidoglycan (formerly called murein).

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Amide in the context of Anandamide

Anandamide (ANA), also referred to as N-arachidonoylethanolamine (AEA), is a fatty acid neurotransmitter belonging to the fatty acid derivative group known as N-acylethanolamines (NAE). Anandamide takes its name from the Sanskrit word ananda (आनन्द), meaning "joy, bliss, delight," plus amide. Anandamide, the first discovered endocannabinoid, engages with the body's endocannabinoid system by binding to the same cannabinoid receptors that THC found in cannabis acts on. Anandamide can be found within tissues in a wide range of animals. It has also been found in plants, such as the cacao tree.

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Amide in the context of Lithium aluminium hydride

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[AlH4] or LiAlH4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.

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Amide in the context of Ceramide

Ceramides are a family of waxy lipid molecules. A ceramide is composed of sphingosine and a fatty acid joined by an amide bond. Ceramides are found in high concentrations within the cell membrane of eukaryotic cells, since they are component lipids that make up sphingomyelin, one of the major lipids in the lipid bilayer. Contrary to previous assumptions that ceramides and other sphingolipids found in cell membrane were purely supporting structural elements, ceramide can participate in a variety of cellular signaling: examples include regulating differentiation, proliferation, and programmed cell death (PCD) of cells.

The word ceramide comes from the Latin cera (wax) and amide. Ceramide is a component of vernix caseosa, the waxy or cheese-like white substance found coating the skin of newborn human infants.

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Amide in the context of Carbonyl reduction

In organic chemistry, carbonyl reduction is the conversion of any carbonyl group, usually to an alcohol. It is a common transformation that is practiced in many ways. Ketones, aldehydes, carboxylic acids, esters, amides, and acid halides - some of the most pervasive functional groups, -comprise carbonyl compounds. Carboxylic acids, esters, and acid halides can be reduced to either aldehydes or a step further to primary alcohols, depending on the strength of the reducing agent. Aldehydes and ketones can be reduced respectively to primary and secondary alcohols. In deoxygenation, the alcohol group can be further reduced and removed altogether by replacement with hydrogen.

Two broad strategies exist for carbonyl reduction. One method, which is favored in industry, uses hydrogen as the reductant. This approach is called hydrogenation and requires metal catalysts. The other broad approach employs stoichiometric reagents that deliver H and H separately. This article focuses on the use of these reagents. Prominent among these reagents are the alkali metal salts of borohydrides and aluminium hydrides.

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Amide in the context of Nonivamide

Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an organic compound and a capsaicinoid. It is an amide of pelargonic acid (n-nonanoic acid) and vanillyl amine. It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin.

Nonivamide is used as a food additive to add pungency to seasonings, flavorings, and spice blends. It is also used in the confectionery industry to create a hot sensation, and in the pharmaceutical industry in some formulations as a cheaper alternative to capsaicin.

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