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Wurster's Cation
Tetramethylphenylenediamine (TMPD) is an organic compound with the formula . It is most studied of three isomers of this formula. It is a colorless solid. With two dimethylamino substituents, the ring is particularly electron rich. Redox behavior One-electron oxidation of TMPD gives the deep blue radical cation called Wurster's blue, . It was one of the first radical cations to be reported. Many properties have been described including its rapid rate of self-exchange: : X-ray crystallography of the TMPD and its iodide salt reveals that oxidation most strongly contracts the C-N(CH3)2 and the HC---CH bonds, indicating that oxidation gives a quinoid-like species. The monocation illustrates an early step in the oxidation of p-phenylenediamine derivatives, which are widely used for hair dying. N,N-Dimethylphenylenediamine () also easily oxidizes to a radical cation, called Wurster's Red. The hydrochloride salt of TMPD has been used as a redox indicator in the oxidase t ...
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Organic Compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes (e.g. methane ) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as certain compounds of carbon with nitrogen and oxygen (e.g. cyanide ion , hydrogen cyanide , chloroformic acid , carbon dioxide , and carbonate ion ). Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, and even ...
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Electron Rich
Electron-rich is jargon that is used in multiple related meanings with either or both kinetic and thermodynamic implications: * with regards to electron-transfer, electron-rich species have low ionization energy and/or are reducing agents. Tetrakis(dimethylamino)ethylene is an electron-rich alkene because, unlike ethylene, it forms isolable radical cation. In contrast, electron-poor alkene tetracyanoethylene is an electron acceptor, forming isolable anions. * with regards to acid-base reactions, electron-rich species have high pKa's and react with weak Lewis acids. * with regards to nucleophilic substitution reactions, electron-rich species are relatively strong nucleophiles, as judged by rates of attack by electrophiles. For example, compared to benzene, pyrrole is more rapidly attacked by electrophiles. Pyrrole is therefore considered to be an electron-rich aromatic ring. Similarly, benzene derivatives with electron-donating groups (EDGs) are attacked by electrophiles faste ...
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Outer Sphere Electron Transfer
Outer sphere refers to an electron transfer (ET) event that occurs between chemical species that remain separate and intact before, during, and after the ET event. In contrast, for inner sphere electron transfer the participating redox sites undergoing ET become connected by a chemical bridge. Because the ET in outer sphere electron transfer occurs between two non-connected species, the electron is forced to move through space from one redox center to the other. Marcus theory The main theory describing the rates of outer sphere electron transfer was developed by Rudolph A. Marcus in the 1950s, for which he was awarded the Nobel Prize in Chemistry in 1992. A major aspect of Marcus theory is the dependence of the electron transfer rate on the thermodynamic driving force (difference in the redox potentials of the electron-exchanging sites). For most reactions, the rates increase with increased driving force. A second aspect is that the rate of outer sphere electron-transfer depends ...
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X-ray Crystallography
X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring the angles and intensities of the X-ray diffraction, a crystallography, crystallographer can produce a three-dimensional picture of the density of electrons within the crystal and the positions of the atoms, as well as their chemical bonds, crystallographic disorder, and other information. X-ray crystallography has been fundamental in the development of many scientific fields. In its first decades of use, this method determined the size of atoms, the lengths and types of chemical bonds, and the atomic-scale differences between various materials, especially minerals and alloys. The method has also revealed the structure and function of many biological molecules, including vitamins, drugs, proteins and nucleic acids such as DNA. X-ray crystall ...
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Hair Dying
Hair coloring, or hair dyeing, is the practice of changing the color of the hair on humans' heads. The main reasons for this are cosmetic: to cover gray or white hair, to alter hair to create a specific look, to change a color to suit preference or to restore the original hair color after it has been discolored by hairdressing processes or sun bleaching. Hair coloring can be done professionally by a hairdresser or independently at home. Hair coloring is very popular, with 50-80% of women in the United States, Europe, and Japan having reported using hair dye. At-home coloring in the United States reached sales of $1.9 billion in 2011 and was expected to rise to $2.2 billion by 2016. History The dyeing of hair is an ancient art that involves treatment of the hair with various chemical compounds. Assyrian herbals dating back to contain some of the oldest recipes for cosmetic preparations known, including hair dye. The ancient Egyptian Ebers Papyrus, , has recipes for dyeing ...
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N,N-Dimethylphenylenediamine
''N'',''N''-Dimethylphenylenediamine is an organic compound with the formula . It is one of the phenylenediamines, a class of compounds that have long attracted attention for their redox properties. This diamine is, for example, easily oxidized to a deep red radical cation, which is called Wurster's Red. The related Wurster's Blue cation has four N-methyl groups Synthesis Dimethyl-4-phenylenediamine is prepared by the nitration of dimethylaniline followed by reduction of the resulting 4-nitrodimethylaniline. A variety of methods have been examined. Applications Dimethyl-4-phenylenediamine can be converted to methylene blue by reaction with dimethylaniline and sodium thiosulfate in several steps: : It reacts with carbon disulfide Carbon disulfide (also spelled as carbon disulphide) is an inorganic compound with the chemical formula and structure . It is also considered as the anhydride of thiocarbonic acid. It is a colorless, flammable, neurotoxic liquid that is used ...
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Redox
Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a decrease in the oxidation state. The oxidation and reduction processes occur simultaneously in the chemical reaction. There are two classes of redox reactions: * Electron transfer, Electron-transfer – Only one (usually) electron flows from the atom, ion, or molecule being oxidized to the atom, ion, or molecule that is reduced. This type of redox reaction is often discussed in terms of redox couples and electrode potentials. * Atom transfer – An atom transfers from one Substrate (chemistry), substrate to another. For example, in the rusting of iron, the oxidation state of iron atoms increases as the iron converts to an oxide, and simultaneously, the oxidation state of oxygen decreases as it accepts electrons r ...
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Oxidase Test
The oxidase test is used to determine whether an organism possesses the cytochrome c oxidase enzyme. The test is used as an aid for the differentiation of ''Neisseria'', ''Moraxella'', ''Campylobacter'' and ''Pasteurella'' species (oxidase positive). It is also used to differentiate pseudomonads from related species.MacFaddin JF, editor. Biochemical Tests for Identification of Medical Bacteria. 3rd ed. Philadelphia:Lippincott Williams and Wilkins; 2000. p. 363-7 Classification Strains may be either oxidase-positive (OX+) or oxidase-negative (OX-). OX+ OX+ normally means the bacterium contains cytochrome c oxidase (also known as Complex IV) and can therefore use oxygen for energy production by converting O2 to H2O2 or H2O with an electron transfer chain. The Pseudomonadaceae are typically OX+. The Gram-negative diplococci Neisseria and Moraxella are oxidase-positive. Many Gram-negative, spiral curved rods are also oxidase-positive, which includes ''Helicobacter pylori'', ''Vibrio ...
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Standard Hydrogen Electrode
In electrochemistry, the standard hydrogen electrode (abbreviated SHE), is a redox electrode which forms the basis of the thermodynamic scale of oxidation-reduction potentials. Its absolute electrode potential is estimated to be at 25 °C, but to form a basis for comparison with all other electrochemical reactions, hydrogen's standard electrode potential () is declared to be zero volts at any temperature. Potentials of all other electrodes are compared with that of the standard hydrogen electrode at the same temperature. Nernst equation for SHE The hydrogen electrode is based on the redox half cell corresponding to the reduction of two hydrated protons, into one gaseous hydrogen molecule, General equation for a reduction reaction: : \underset + z\ce\ \underset The reaction quotient () of the half-reaction is the ratio between the chemical activities () of the reduced form (the reductant, ) and the oxidized form (the oxidant, ). : Q_r = \frac Considering the ...
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Potentiometric Titration
In analytical chemistry, potentiometric titration is a technique similar to direct titration of a redox reaction. It is a useful means of characterizing an acid. No indicator is used; instead the electric potential is measured across the analyte, typically an electrolyte solution. To do this, two electrodes are used, an indicator electrode (the glass electrode and metal ion indicator electrode) and a reference electrode. Reference electrodes generally used are hydrogen electrodes, calomel electrodes, and silver chloride electrodes. The indicator electrode forms an electrochemical half-cell with the ions of interest in the test solution. The reference electrode forms the other half-cell. The overall electric potential is calculated as :E_ = E_ - E_ + E_. is the potential drop over the test solution between the two electrodes. is recorded at intervals as the titrant is added. A graph of potential against volume added can be drawn and the end point of the reaction is halfway betw ...
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