Ethynyl Compounds
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Ethynyl Compounds
In organic chemistry, an ethynyl group is a functional group with the formula −C≡CH, representing an acetylene molecule with one fewer hydrogen atom. * Ethynyl group (HC≡C–), also designated as an acetylenic group (from acetylene), is referred to in IUPAC chemical nomenclature with the -yne suffix. It is sometimes designated as ''ethinyl'' in compounds such as ethinylestradiol and ethisterone (ethinyltestosterone). See main page alkynes. See also * Ethynylation * Ethynyl radical * Propynyl (H3C–C≡C–R, 1-propynyl group; or HC≡C–CH2–R, 2-propynyl group, Propargyl In organic chemistry, the propargyl group is a functional group of 2- propynyl with the structure . It is an alkyl group derived from propyne (). The term propargylic refers to a saturated position ( ''sp''3-hybridized) on a molecular framework ...) Alkynyl groups {{hydrocarbon-stub ...
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Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes Physical property, physical and Chemical property, chemical properties, and evaluation of Reactivity (chemistry), chemical reactivity to understand their behavior. The study of organic reactions includes the organic synthesis, chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical (in silico) study. The range of chemicals studied chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but a ...
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Acetylene
Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure form and thus is usually handled as a solution. Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities such as divinyl sulfide and phosphine.Compressed Gas Association (1995Material Safety and Data Sheet – Acetylene As an alkyne, acetylene is Saturated and unsaturated compounds, unsaturated because its two carbon atoms are Chemical bond, bonded together in a triple bond. The carbon–carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°. The triple bond in acetylene results in a high energy content that is released when acetylene is burned. Discovery Acetylene was discovered in 1836 by Edmund Davy, who identified it as a "new carburet ...
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-yne
In chemistry, the suffix ''-yne'' is used to denote the presence of a triple bond (). The suffix follows IUPAC nomenclature, and is mainly used in organic chemistry. However, inorganic compounds featuring unsaturation in the form of triple bonds may be denoted by substitutive nomenclature with the same methods used with alkynes, i.e., the name of the corresponding saturated hydride is modified by replacing the "''-ane''" ending with "''-yne''". The suffix "''-diyne''" is used when there are two triple bonds, and so on. The position of unsaturation is indicated by a numerical locant immediately preceding the "''-yne''" suffix, or locants in the case of multiple triple bonds. Locants are chosen to be as low as possible. While generally used as a suffix, "''-yne''" is also used as an infix to name substituent groups that are triply bound to the parent compound. This suffix arose as a collapsed form of the end of the word ''acetylene''. The final "''-e''" disappears if it is fol ...
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Ethinylestradiol
Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. Ethinylestradiol was widely used for various indications such as the treatment of menopausal symptoms, gynecological disorders, and certain hormone-sensitive cancers. It is usually taken by mouth but is also used as a patch and vaginal ring. The general side effects of ethinylestradiol include breast tenderness and enlargement, headache, fluid retention, and nausea among others. In males, ethinylestradiol can additionally cause breast development, feminization in general, hypogonadism, and sexual dysfunction. Rare but serious side effects include blood clots, liver damage, and cancer of the uterus. Ethinylestradiol is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol. It is a synthetic derivative of estradiol, a natural estrogen, and differs from it in various ways. Compared to estradiol, e ...
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Ethisterone
Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen (medication), estrogen. The medication is taken oral administration, by mouth. Side effects of ethisterone include virilization, masculinization among others. Ethisterone is a progestin, or a synthetic compound, synthetic progestogen (medication), progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has some androgenic and anabolic activity and no other important hormonal agent, hormonal activity. Ethisterone was discovered in 1938 and was introduced for medical use in Germany in 1939 and in the United States in 1945. It was the second progestogen ( ...
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Alkyne
\ce \ce Acetylene \ce \ce \ce Propyne \ce \ce \ce \ce 1-Butyne In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula . Alkynes are traditionally known as acetylenes, although the name ''acetylene'' also refers specifically to , known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic. Structure and bonding In acetylene, the H–C≡C bond angles are 180°. By virtue of this bond angle, alkynes are rod-like. Correspondingly, cyclic alkynes are rare. Benzyne cannot be isolated. The C≡C bond distance of 118 picometers (for C2H2) is much shorter than the C=C distance in alkenes (132 pm, for C2H4) or the C–C bond in alkanes (153 pm). : The triple bond is very strong with a bond strength of 839 kJ/mol. ...
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Alkynation
In organic chemistry, alkynylation is an addition reaction in which a terminal alkyne () is added to a carbonyl group In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such as aldehydes ... () to form an Alpha and beta carbon, α-alkynyl alcohol (chemistry), alcohol (). When the acetylide is formed from acetylene (), the reaction gives an α-ethynyl alcohol. This process is often referred to as ethynylation. Such processes often involve metal acetylide intermediates. Scope The principal reaction of interest involves the addition of the acetylene () to a ketone () or aldehyde (): :RR'C=O + HC#CR'' -> RR'C(OH)C#CR'' The reaction proceeds with retention of the triple bond. For aldehydes and unsymmetrical ketones, the product is chiral, hence there is interest in asymmetric variants. These reactions ...
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Ethynyl Radical
The ethynyl radical (systematically named λ3-ethyne and hydridodicarbon(''C''—''C'')) is an organic compound with the chemical formula C≡CH (also written CHor ). It is a simple molecule that does not occur naturally on Earth but is abundant in the interstellar medium. It was first observed by electron spin resonance isolated in a solid argon matrix at liquid helium temperatures in 1963 by Cochran and coworkers at the Johns Hopkins Applied Physics Laboratory. It was first observed in the gas phase by Tucker and coworkers in November 1973 toward the Orion Nebula, using the NRAO 11-meter radio telescope. It has since been detected in a large variety of interstellar environments, including dense molecular clouds, bok globules, star forming regions, the shells around carbon-rich evolved stars, and even in other galaxies. Astronomical importance Observations of C2H can yield a large number of insights into the chemical and physical conditions where it is located. First, the re ...
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Propynyl
In organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ..., a propynyl group is a propyl bearing a triple bond. * The 1-propynyl group has the structure CH3-C≡C–R. * The 2-propynyl group is also known as a propargyl group, and has the structure HC≡C−CH2–R. References Alkynyl groups {{Organic-chem-stub ...
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Propargyl
In organic chemistry, the propargyl group is a functional group of 2- propynyl with the structure . It is an alkyl group derived from propyne (). The term propargylic refers to a saturated position ( ''sp''3-hybridized) on a molecular framework next to an alkynyl group. The name comes from mix of ''propene'' and ''argentum'', which refers to the typical reaction of the terminal alkynes with silver salts. The term homopropargylic designates in the same manner * a saturated position on a molecular framework next to a propargylic group and thus two bonds from an alkyne moiety. * a 3-butynyl fragment, , or substituted homologue. See also * Alkenyl groups ** Allyl ** Vinyl group * Ethynyl In organic chemistry, an ethynyl group is a functional group with the formula −C≡CH, representing an acetylene molecule with one fewer hydrogen atom. * Ethynyl group (HC≡C–), also designated as an acetylenic group (from acetylene), is refer ... * Propargyl chloride * Propargyl alcoh ...
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