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Tris(triphenylphosphine)ruthenium Dichloride
Dichlorotris(triphenylphosphine)ruthenium(II) is a coordination complex of ruthenium. It is a chocolate brown solid that is soluble in organic solvents such as benzene. The compound is used as a precursor to other complexes including those used in homogeneous catalysis. Synthesis and basic properties RuCl2(PPh3)3 is the product of the reaction of ruthenium trichloride trihydrate with a methanolic solution of triphenylphosphine. :2 RuCl3(H2O)3 + 7 PPh3 → 2 RuCl2(PPh3)3 + 2 HCl + 5 H2O + OPPh3 The coordination sphere of RuCl2(PPh3)3 can be viewed as either five-coordinate or octahedral. One coordination site is occupied by one of the hydrogen atoms of a phenyl group. This Ru---H agostic interaction is long (2.59 Å) and weak. The low symmetry of the compound is reflected by the differing lengths of the Ru-P bonds: 2.374, 2.412, and 2.230 Å. The Ru-Cl bond lengths are both 2.387 Å. Reactions In the presence of excess of triphenylphosphine, RuCl2(PPh3)3 binds a fourth phosphine ...
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Coordination Complex
A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many metal-containing chemical compound, compounds, especially those that include transition metals (elements like titanium that belong to the periodic table's d-block), are coordination complexes. Nomenclature and terminology Coordination complexes are so pervasive that their structures and reactions are described in many ways, sometimes confusingly. The atom within a ligand that is bonded to the central metal atom or ion is called the donor atom. In a typical complex, a metal ion is bonded to several donor atoms, which can be the same or different. A Ligand#Polydentate and polyhapto ligand motifs and nomenclature, polydentate (multiple bonded) ligand is a molecule or ion that bonds to the central atom ...
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Kharasch Addition Dichlorotris(triphenylphosphine)ruthenium(II)
Morris Selig Kharasch (August 24, 1895 – October 9, 1957) was a pioneering organic chemist best known for his work with free radical additions and polymerizations. He defined the peroxide effect, explaining how an anti-Markovnikov orientation could be achieved via free radical addition. Kharasch was born in the Russian Empire in 1895 and immigrated to the United States at the age of 13. In 1919, he completed his Ph.D. in chemistry at the University of Chicago and spent most of his professional career there. Most of his research in the 1920s focused on organo-mercuric derivatives. He synthesized an important anti-microbial alkyl mercuric sulfur compound, thimerosal, commercially known as Merthiolate, which he patented in 1928 and assigned to the pharmaceutical company Eli Lilly and Company. Merthiolate was introduced as a vaccine preservative in 1931, and by the late 1980s thimerosal was used in all whole-cell DPT vaccines. Nobel laureate Herbert C. Brown was one of his student ...
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Chloro Complexes
Chlorine is a chemical element; it has symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine. Chlorine played an important role in the experiments conducted by medieval alchemists, which commonly involved the heating of chloride salts like ammonium chloride ( sal ammoniac) and sodium chloride ( common salt), producing various chemical substances containing chlorine such as hydrogen chloride, mercury(II) chloride (corrosive sublimate), and . However, the nature of free chlorine gas as a separate substance was only recognised around 1630 by Jan Baptist van Helmont. Car ...
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Triphenylphosphine Complexes
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether. Preparation and structure Triphenylphosphine can be prepared in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium. The industrial synthesis involves the reaction between phosphorus trichloride, chlorobenzene, and sodium: :PCl3 + 3 PhCl + 6 Na → PPh3 + 6 NaCl Triphenylphosphine crystallizes in triclinic and monoclinic modification. In both cases, the molecule adopts a pyramidal structure with propeller-like arrangement of the three ...
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Ruthenium Complexes
Ruthenium is a chemical element; it has symbol Ru and atomic number 44. It is a rare transition metal belonging to the platinum group of the periodic table. Like the other metals of the platinum group, ruthenium is unreactive to most chemicals. Karl Ernst Claus, a Russian scientist of Baltic-German ancestry, discovered the element in 1844 at Kazan State University and named it in honor of Russia. (He used the Latin name ''Ruthenia'', which can have other meanings, but specifically stated that the element was named in honor of his "motherland".) Ruthenium is usually found as a minor component of platinum ores; the annual production has risen from about 19 tonnes in 2009 to some 35.5 tonnes in 2017. Most ruthenium produced is used in wear-resistant electrical contacts and thick-film resistors. A minor application for ruthenium is in platinum alloys and as a chemical catalyst. A new application of ruthenium is as the capping layer for extreme ultraviolet photomasks. Ru ...
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Alcohol Cross Coupling RuCl2PPH3
Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alcoholic drink * Rubbing alcohol, for sanitation and to kill germs Music * "Alcohol", a song by Barenaked Ladies from the 1998 album ''Stunt'' * "Alcohol", a song by Beck from the 1993 single " Loser" * "Alcohol" (Brad Paisley song), 2005 * "Alcohol", a song by Butthole Surfers from the 1993 album ''Independent Worm Saloon'' * "Alcohol", a song by CSS from the 2005 album ''Cansei de Ser Sexy'' * "Alcohol", a song by Gang Green from the 1986 album ''Another Wasted Night'' * "Alcohol", a song by Gogol Bordello from the 2007 album '' Super Taranta!'' * "Alcohol", a song by the Kinks from the 1977 album ''Muswell Hillbillies'' and ''Everybody's in Show-Biz'' * "Alcohol", a song by Millionaires, 2008 * "Alcohol", a song by Terminaator from the 19 ...
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Lewis Acid
A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any species that has a filled orbital containing an electron pair which is not involved in bonding but may form a dative bond with a Lewis acid to form a Lewis adduct. For example, NH3 is a Lewis base, because it can donate its lone pair of electrons. Trimethylborane CH3)3Bis a Lewis acid as it is capable of accepting a lone pair. In a Lewis adduct, the Lewis acid and base share an electron pair furnished by the Lewis base, forming a dative bond. In the context of a specific chemical reaction between NH3 and Me3B, a lone pair from NH3 will form a dative bond with the empty orbital of Me3B to form an adduct NH3•BMe3. The terminology refers to the contributions of Gilbert N. Lewis. From p. 142: "We are inclined to think of substances as ...
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Borrowing Hydrogen
Hydrogen auto-transfer, also known as borrowing hydrogen, is the activation of a chemical reaction by temporary transfer of two hydrogen atoms from the reactant to a catalyst and return of those hydrogen atoms back to a reaction intermediate to form the final product. Two major classes of borrowing hydrogen reactions exist: (a) those that result in hydroxyl substitution, and (b) those that result in carbonyl addition. In the former case, alcohol dehydrogenation generates a transient carbonyl compound that is subject to condensation followed by the return of hydrogen. In the latter case, alcohol dehydrogenation is followed by reductive generation of a nucleophile, which triggers carbonyl addition. As borrowing hydrogen processes avoid manipulations otherwise required for discrete alcohol oxidation and the use of stoichiometric organometallic reagents, they typically display high levels of atom-economy and, hence, are viewed as examples of Green chemistry. History The Guerbet reac ...
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Imines
In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions. Distinction is sometimes made between aldimines and ketimines, derived from aldehydes and ketones, respectively. Structure In imines the five core atoms (C2C=NX, ketimine; and C(H)C=NX, aldimine; X = H or C) are coplanar. Planarity results from the sp2-hybridization of the mutually double-bonded carbon and the nitrogen atoms. The C=N distance is 1.29–1.31 Å for nonconjugated imines and 1.35 Å for conjugated imines. By contrast, C−N distances in amines and nitriles are 1.47 and 1.16 Å respectively. Rotation about the C=N bond is slow. Using NMR spectroscopy, both ''E'' and ''Z'' isomers of aldimines h ...
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Carboxylic Acids
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl group (e.g., alkyl, alkenyl, aryl), or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion. Examples and nomenclature Carboxylic acids are commonly identified by their trivial names. They often have the suffix ''-ic acid''. IUPAC-recommended names also exist; in this system, carboxylic acids have an ''-oic acid'' suffix. For example, butyric acid () is butanoic acid by IUPAC guidelines. For nomenclature of complex molecules containing a carboxylic acid, the carboxyl can be considered position one of the parent chain even if there are other substituents, such as 3-chloropropanoic acid. Alternately, it can be named ...
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Ketones
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' are methyl), with the formula . Many ketones are of great importance in biology and industry. Examples include many sugars (ketoses), many steroids, ''e.g.'', testosterone, and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considered retained IUPAC names, although some introd ...
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