Nitrogen-containing Compounds

Amines are chemical compounds which have the general formula R₃N (R being an alkyl or aryl group). Amines are derivatives of ammonia in which one or more of the hydrogen atoms are replaced by an alkyl or aryl group. Depending on the number of R groups, amines are classified as primary, secondary, or tertiary amines. In organic chemistry, amines are used in the synthesis of numerous derivatives which are endowed with useful properties, such as amino alcohols, amino acids, amides, lactams, imino derivatives, azo compounds, hydrazines, hydrazones, and ureas.

Amines and amine derivatives have a wide range of biological functions, such as the critical role of amino acids in biology. Amino acids are the building blocks of proteins and peptides. Apart from proteins, amino acids perform critical roles in processes such as neurotransmitter transport and biosynthesis. Amine derivatives also play a vital role in pharmaceutical research. Many drugs, such as those with antiviral and antibacterial activities, contain amino compounds or their derivatives. Amines and other derived compounds are used for a number of research applications in laboratory settings—amines, for example, act as good ligands in coordination chemistry.

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An amide, or an acid amide, is a compound with the functional group C(=O)N(R₁R₂). Cyclic amides are called lactams. Lactam compounds would be either secondary or tertiary amides. Lactams, depending on the ring size, bear the name α-lactam (3 ring atoms), β-lactam (4 ring atoms), γ-lactam (5 ring atoms), δ-lactam (6 ring atoms), or ε-lactam (7 ring atoms). The β-lactam ring is part of the core structure of several antibiotic families, such as the penicillins, cephalosporins, carbapenems, and monobactams. Amides undergo various chemical reactions, usually through an attack on the carbonyl group. There are many renowned organic reactions which involve amides, including the Hofmann rearrangement and the Vilsmeier-Haack reaction.

Amides are commonly formed by reacting a carboxylic acid with an amine. Other well-known reactions for the amide preparation include the Chapman rearrangement, the Bodroux reaction, and the Schmidt reaction. The Beckmann rearrangement is an acid-catalyzed rearrangement of an oxime to an amide. Many cyclic amides are prepared using this rearrangement. Following the rearrangement, cyclohexanone produces caprolactam which is the feedstock in the production of nylon 6.

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Organic compounds which have a -CN functional group are called nitriles, or cyanocompounds. Organic compounds containing a nitrile group are referred to as cyanocarbons. Nitriles are polar compounds with high dielectric constants. Nitriles are available naturally in both plant and animal sources. More than 120 nitriles have been isolated from terrestrial and marine sources. Cabbage, brussels sprouts, and cauliflower are a few examples of plants which contain nitriles.

In organic chemistry, a nitrile compound can undergo various reactions such as reduction, addition, oxidation, hydrolysis, and elimination. The Blaise reaction and Pinner reaction are some of the named reactions wherein nitrile acts as an electrophile. The Thorpe reaction is characterized by self-condensation of nitriles via nucleophilic addition.

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Since the discovery of organic azides by Peter Grie more than 150 years ago, numerous syntheses of energy-rich azide molecules have been developed. In more recent times in particular, the use of azides in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis has been extensively explored. Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science.

For the synthesis of various types of organic compounds, several thermodynamically favored reactions have been identified that lead specifically to one product, such as nucleophilic ring opening reactions of epoxides and aziridines; non-aldol type carbonyl reactions, such as formation of hydrazones and heterocycles; additions to carbon-carbon multiple bonds, such as oxidative formation of epoxides and Michael additions; and cycloaddition reactions. Well-known reactions such as the aza-Wittig reaction, Sundberg rearrangement, Staudinger reaction, Boyer and Boyer-Aub rearrangements, Curtius rearrangement, Schmidt rearrangement, and Hemetsberger rearrangement exemplify the versatile nature of azides.

Hydrazine derivatives are a class of organic compounds having the general chemical formula RNHNHR. Hydrazine is a convenient reducing agent and is used to reduce metal salts and oxides to pure metals. It is also used as an antioxidant, oxygen scavenger, and corrosion inhibitor in water boilers and heating systems. Hydrazine is used in the Wolff-Kishner reduction of converting a ketone into an alkane.

Aryl hydrazines are employed to prepare a large variety of indoles via the Fischer indole synthesis. Alkyl and arylhydrazines are useful for generating several heterocycles of pharmacological importance. Arylhydrazines can be used in the resolution of racemic N-protected amino acids. As a practical approach for an array of substituted biaryls, phenylhydrazine can serve as initiator for efficient direct radical arylation of unactivated arenes, as described by Dewanji, et al.

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Other Thermo Scientific organonitrogen compounds, suitable for a range of laboratory applications, include azo compounds, imines and imino compounds, nitroso compounds, and more.

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