Phenyldiazonium cation

Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group with the characteristic structure of R-N₂⁺ X^- where R can be any organic residue such alkyl or aryl and X is an inorganic or organic anion such as a halogen. Historically, diazonium salts have been developed as important intermediates in the organic synthesis of dyes. An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with the exception of carbides, carbonates, carbon oxides and gases containing carbon. ... In ecology functional groups are collections of organisms based on morphological, physiological, behavioral, biochemical, or environmental responses or on trophic criteria. ... An Alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... An aryl is a functional group of an organic molecule derived from an aromatic compound such as benzene. ... The halogens are a chemical series. ... Organic synthesis is the construction of organic molecules via chemical processes. ... Yarn drying after being dyed in the early American tradition, at Conner Prairie living history museum. ...

Diazonium salt synthesis

The most important method for the preparation of diazonium salts is treatment of aromatic amines such as aniline with sodium nitrite in the presence of a mineral acid. These salts slowly decompose even at low temperatures and therefore used immediately in secondary reactions. This article needs to be cleaned up to conform to a higher standard of quality. ... Sodium nitrite, with chemical formula NaNO2, also called nitrous acid, sodium salt, is used as a color fixative and preservative in meats and fish. ... A mineral acid is an acid derived from inorganic minerals by chemical reaction as opposed to organic acids. ...

Diazonium salt reactions

The most important aromatic diazonium salt reactions are azo coupling with anilines and phenols to azo compounds (azo dyes) in electrophilic aromatic substitution and nitrogen replacement reactions by halogens in nucleophilic aromatic substitution such as the Sandmeyer Reaction. An azo coupling is an organic reaction between a diazonium compound and an aniline or a phenol. ... In chemistry, azo compounds generally have a molecular formula of the form R-N=N-R, in which R and R can be either aromatic or aliphatic. ... Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, in an aromatic system is replaced by an electrophile. ... The halogens are a chemical series. ... A Nucleophilic aromatic substitution is a type of substitution reaction in organic chemistry. ... In chemistry, the Sandmeyer Reaction is he preparation of aryl chlorides and bromides by reaction of an arenediazonium salt with the corresponding copper(I) halide. ...

Applications

Diazonium salts are light sensitive and break down upon exposure to UV light. This property has led to their use in document reproduction. In this process, paper or film is coated with a diazonium salt. After contact exposure under UV light, the paper is exposed to ammonium hydroxide vapors which results in the production of an azodye leading to a dye image. Ammonium hydroxide (NH4OH) is a name sometimes given to an aqueous solution of ammonia. ...

In another application of diazonium salts, 4-chlorobenzenediazonium tetrafluoroborate is very efficient in functionalizing single wall nanotubes ^[1]. In order to exfoliate the nanotubes they are mixed with an ionic liquid in a mortar and pestle. The diazonium salt is added together with potassium carbonate and after 15 minutes of grinding at room temperature the surface of the nanotubes are covered with chlorophenyl groups with an efficiency of 1 in 44 carbon atoms. These added substituents prevent the tubes from forming intimate bundles due to large cohesive forces between them which is a reoccurring problem in nanotube technology. An electronic device known as a diode can be formed by joining two nanoscale carbon tubes with different electronic properties. ... Exfoliation has at least two meanings: In cosmetology, exfoliation is a cosmetic technique aimed at removing dead skin cells from the face and body. ... An ionic liquid is a liquid that contains only ions. ... Mortar and pestle A mortar and pestle are two tools used with each other to grind and mix substances. ... Potassium carbonate is a white salt, soluble in water (insoluble in alcohol), which forms a strongly alkaline solution. ... Room temperature, in laboratory reports, is taken to be roughly 21–23 degrees Celsius (72 degrees Fahrenheit), or 294–296 kelvins. ... In organic chemistry, a substituent is an atom or group of atoms subsituted in place of a hydrogen atom on the parent chain of a hydrocarbon. ...

External links

• Michigan State Chemistry website

References

1. ^  J. Am. Chem. Soc.; 2005; 127(42) pp 14867 - 14870; DOI: 10.1021/ja053998c Abstract