Pyridinium Compounds
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Pyridinium Compounds
Pyridinium refers to the cation . It is the conjugate acid of pyridine. Many related cations are known involving substituted pyridines, e.g. picolines, lutidines, collidines. They are prepared by treating pyridine with acids. As pyridine is often used as an organic base in chemical reactions, pyridinium salts are produced in many acid-base reactions. Its Salt (chemistry), salts are often insoluble in the organic solvent, so Precipitation (chemistry), precipitation of the pyridinium leaving group complex is an indication of the progress of the reaction. Pyridinium cations are aromatic, as determined through Hückel's rule. They are isoelectronic with benzene. ''N''-Alkylpyridinium cations When the acidic proton is replaced by alkyl, the compounds are called ''N''-alkylpyridinium. A simple representative is Methylpyridinium, ''N''-methylpyridinium (). These pyridinium intermediates have been used as electrophiles in synthetic organic chemistry to build dearomatized congeners calle ...
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Pyridine
Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated Polymer, polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide. Properties Physical properties Pyridine is diamagnetism, diamagnetic. Its critical point (thermodynamics), critical parameters are: pressure 5.63 MPa, temperature 619 K and volume 248 cm3/mol. In the temperatur ...
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Hückel's Rule
In organic chemistry, Hückel's rule predicts that a planar ring molecule will have aromatic properties if it has 4''n'' + 2 π-electrons, where ''n'' is a non-negative integer. The quantum mechanical basis for its formulation was first worked out by physical chemist Erich Hückel in 1931. The succinct expression as the 4''n'' + 2 rule has been attributed to W. v. E. Doering (1951), although several authors were using this form at around the same time. In agreement with the Möbius–Hückel concept, a cyclic ring molecule follows Hückel's rule when the number of its π-electrons equals 4''n'' + 2, although clearcut examples are really only established for values of ''n'' = 0 up to about ''n'' = 6. Hückel's rule was originally based on calculations using the Hückel method, although it can also be justified by considering a particle in a ring system, by the LCAO method and by the Pariser–Parr–Pople method. Aroma ...
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Pyridinium Chlorochromate
Pyridinium chlorochromate (PCC) is a yellow-orange salt (chemistry), salt with the chemical formula, formula [C5H5NH]+[CrO3Cl]−. It is a reagent in organic synthesis used primarily for organic redox reaction, oxidation of Alcohol (chemistry), alcohols to form carbonyls. A variety of related compounds are known with similar reactivity. PCC offers the advantage of the selective oxidation of alcohols to aldehydes or ketones, whereas many other reagents are less selective. Structure and preparation PCC consists of a pyridinium cation, [C5H5NH]+, and a tetrahedral chlorochromate anion, [CrO3Cl]−. Related salts are also known, such as 1-butylpyridinium chlorochromate, [C5H5N(C4H9)][CrO3Cl] and potassium chlorochromate. PCC is commercially available. Serendipity, Discovered by accident, the reagent was originally prepared via addition of pyridine into a cold solution of chromium trioxide in concentrated hydrochloric acid: :C5H5N + HCl + CrO3 → [C5H5NH][CrO3Cl] In one alternative ...
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Paraquat
Paraquat ( trivial name; ), or ''N'',''N''′-dimethyl-4,4′-bipyridinium dichloride (systematic name), also known as methyl viologen, is a toxic organic compound with the chemical formula C6H7N)2l2. It is classified as a viologen, a family of redox-active heterocycles of similar structure. It is one of the most widely used herbicides worldwide. It is quick-acting and non-selective, killing green plant tissue on contact. Paraquat is highly toxic to humans and other animals. The toxicity and lethality depends on the dose and how the herbicide is absorbed by the body. In humans, paraquat damages the mouth, stomach, and intestines if it is ingested orally. Once absorbed in the body, paraquat causes particular damage to the lungs, kidneys, and liver. Paraquat's lethality is attributed to its enhancing production of superoxide anions and human lung cells can accumulate paraquat. Paraquat exposure has been strongly linked to the development of Parkinson's disease. Paraquat may be ...
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Herbicide
Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page for EPA reports on pesticide use ihere Selective herbicides control specific weed species while leaving the desired crop relatively unharmed, while non-selective herbicides (sometimes called "total weed killers") kill plants indiscriminately. The combined effects of herbicides, nitrogen fertilizer, and improved cultivars has increased yields (per acre) of major crops by three to six times from 1900 to 2000. In the United States in 2012, about 91% of all herbicide usage, was determined by weight applied, in agriculture. In 2012, world pesticide expenditures totaled nearly US$24.7 billion; herbicides were about 44% of those sales and constituted the biggest portion, followed by insecticides, fungicides, and fumigants. Herbicide is also used ...
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Methylpyridinium
Methylpyridinium is an ion with the formula . It is the ''N''-methylated derivative of pyridine. It confers no color to its salts. The ion is classified as a quaternary ammonium ion. Preparation and occurrence Methylpyridinium is prepared by treating pyridine with dimethylsulfate: : It is found in some coffee products. It is not present in unroasted coffee beans, but is formed during roasting from its precursor chemical, trigonelline. Ionic liquid The chloride salt of ''N''-methylpyridinium behaves as an ionic liquid. Mixtures of that salt and zinc chloride have been characterised over the temperature range . See also * Pyridinium * 4-Caffeoyl-1,5-quinide 4-Caffeoyl-1,5-quinide (4-caffeoylquinic-1,5-lactone or 4-CQL) is found in roasted coffee beans. It is formed by lactonization of 4-''O''-caffeoylquinic acid during the roasting process. : It is reported to possess opioid antagonist properties i ... * References Pyridinium compounds Ionic liquids Cations ...
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Alkyl
In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a Ring (chemistry), ring and has the general formula . Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula . Related concepts Alkylation is the addition of alkyl groups to molecules, often by alkylating agents such as Haloalkane, alkyl halides. Alkylating antineoplastic agents are a class of compounds that are used to treat cancer. In such case, the term alkyl is used loosely. For example, nitrogen mustards are well-known alkylating agents, but they are not simple hydrocarbons. In chemistry, alkyl is a group, a substituent, that is attached to ot ...
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NAD+ Phys
Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an adenine nucleobase and the other, nicotinamide. NAD exists in two forms: an oxidized and reduced form, abbreviated as NAD and NADH (H for hydrogen), respectively. In cellular metabolism, NAD is involved in redox reactions, carrying electrons from one reaction to another, so it is found in two forms: NAD is an oxidizing agent, accepting electrons from other molecules and becoming reduced; with H+, this reaction forms NADH, which can be used as a reducing agent to donate electrons. These electron transfer reactions are the main function of NAD. It is also used in other cellular processes, most notably as a substrate of enzymes in adding or removing chemical groups to or from proteins, in posttranslational modifications. Because of the importanc ...
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Benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly Combustibility and flammability, flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline. It is used primarily as a Precursor (chemistry), precursor to the manufacture of chemicals with more complex structures, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene is a major Chemical industry, industrial che ...
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Isoelectronic
Isoelectronicity is a phenomenon observed when two or more molecules have the same structure (positions and connectivities among atoms) and the same electronic configurations, but differ by what specific elements are at certain locations in the structure. For example, , , and are isoelectronic, while and = are not. This definition is sometimes termed valence isoelectronicity. Definitions can sometimes be not as strict, sometimes requiring identity of the total electron count and with it the entire electronic configuration. More usually, definitions are broader, and may extend to allowing different numbers of atoms in the species being compared.A. A. Aradi & T. P. Fehlner, "Isoelectronic Organometallic Molecules", in F. G. A. Stone & Robert West (eds.) ''Advances in Organometallic Chemistry Vol. 30'' (1990), Chapter 5 (at p. 190google books link/ref> The importance of the concept lies in identifying significantly related species, as pairs or series. Isoelectronic specie ...
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Aromatic
In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugation alone. The earliest use of the term was in an article by August Wilhelm Hofmann in 1855. There is no general relationship between aromaticity as a chemical property and the olfaction, olfactory properties of such compounds. Aromaticity can also be considered a manifestation of cyclic delocalization and of Resonance (chemistry), resonance. This is usually considered to be because electrons are free to cycle around circular arrangements of atoms that are alternately single- and double-covalent bond, bonded to one another. This commonly seen model of aromatic rings, namely the idea that benzene was formed from a six-membered carbon ring with alternating single and double bonds (cyclohexatriene), was developed by Friedrich August Kekulé ...
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Cation
An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convention. The net charge of an ion is not zero because its total number of electrons is unequal to its total number of protons. A cation is a positively charged ion with fewer electrons than protons (e.g. K+ ( potassium ion)) while an anion is a negatively charged ion with more electrons than protons (e.g. Cl− ( chloride ion) and OH− ( hydroxide ion)). Opposite electric charges are pulled towards one another by electrostatic force, so cations and anions attract each other and readily form ionic compounds. Ions consisting of only a single atom are termed ''monatomic ions'', ''atomic ions'' or ''simple ions'', while ions consisting of two or more atoms are termed polyatomic ions or ''molecular ions''. If only a + or − is present, it indic ...
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