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Thiourea
Thiourea () is an organosulfur compound with the formula and the structure . It is structurally similar to urea (), with the oxygen atom replaced by sulfur atom (as implied by the '' thio-'' prefix). The properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. Thioureas are a broad class of compounds with the formula Structure and bonding Thiourea is a planar molecule. The C=S bond distance is 1.71 Å. The C-N distances average 1.33 Å. The weakening of the C-S bond by C-N pi-bonding is indicated by the short C=S bond in thiobenzophenone, which is 1.63 Å. Thiourea occurs in two tautomeric forms, of which the thione form predominates in aqueous solutions. The equilibrium constant has been calculated as ''K''eq is . The thiol form, which is also known as an isothiourea, can be encountered in substituted compounds such as isothiouronium salts. : Production The global annual production of thiourea is around 8,000 tonnes, mo ...
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Thiourea Tautomers (cropped)
Thiourea () is an organosulfur compound with the formula and the structure . It is structurally similar to urea (), with the oxygen atom replaced by sulfur atom (as implied by the ''thio-'' prefix). The properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. Thioureas are a broad class of compounds with the formula Structure and bonding Thiourea is a planar molecule. The C=S bond distance is 1.71 Å. The C-N distances average 1.33 Å. The weakening of the C-S bond by C-N pi-bonding is indicated by the short C=S bond in thiobenzophenone, which is 1.63 Å. Thiourea occurs in two tautomeric forms, of which the thione form predominates in aqueous solutions. The equilibrium constant has been calculated as ''K''eq is . The thiol form, which is also known as an isothiourea, can be encountered in substituted compounds such as isothiouronium salts. : Production The global annual production of thiourea is around 8,000 tonnes, mostly in ...
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Thioureas
In organic chemistry, thioureas are members of a family of organosulfur compounds with the formula and structure . The parent member of this class of compounds is thiourea (). Substituted thioureas are found in several commercial chemicals. Structure and bonding Thioureas have a trigonal planar molecular geometry of the core. The bond distance is near 1.71  Å, which is 0.1 Å longer than in normal ketones (). The C–N bond distances are short. Thioureas occurs in two tautomeric forms. : On the other hand, some compounds depicted as isothioureas and in fact thioureas, one example being mercaptobenzimidazole. Synthesis ''N'',''N''′-unsubstituted thioureas can be prepared by treating the corresponding cyanamide with hydrogen sulfide or similar sulfide sources. Organic ammonium salts react with potassium thiocyanate as the source of the thiocarbonyl (). Alternatively, ''N'',''N''′-disubstituted thioureas can be prepared by coupling two amines with thiophosgen ...
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Thiourea Dioxide
Thiourea dioxide or thiox is an organosulfur compound that is used in the textile industry. It functions as a reducing agent. It is a white solid, and exhibits tautomerism in solution. Structure Crystalline and gaseous thiourea dioxide adopts a C2v-symmetric structure. Selected bond lengths: S-C = 186, C-N = 130, and S-O = 149 pm. The sulfur center is pyramidal. The C-S bond length is close to that of a single bond. For comparison, the C=S bond in thiourea is 171 pm. Instead the bonding is described with a significant contribution from a dipolar resonance structure with multiple bonding between C and N. One consequence of this bonding is the planarity of the nitrogen centers. In the presence of water or DMSO, thiourea dioxide converts to the tautomer, a sulfinic acid, (H2N)HN=CS(O)(OH), named formamidine sulfinic acid. Synthesis Thiourea dioxide was first prepared in 1910 by the English chemist Edward de Barry Barnett. Thiourea dioxide is prepared by the oxidation of thiourea ...
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Selenourea
Selenourea is the organoselenium compound with the chemical formula . It is a white solid. This compound features a rare example of a stable, unhindered carbon-selenium double bond. The compound is used in the synthesis of selenium heterocycles. Selenourea is a selenium analog of urea . Few studies have been done on the compound due to the instability and toxicity of selenium compounds. Selenourea is toxic if inhaled or consumed. Synthesis The compound was first synthesized in 1884 by Auguste Verneuil by the reaction of hydrogen selenide and cyanamide: : While this reaction has even found use in industrial synthesis of selenourea, more modern methods concern themselves with synthesis of substituted selenoureas. These can be synthesized using organic isoselenocyanates and secondary amines: : Alternatively, isocyanides react with amines in the presence of elemental selenium: : Properties X-ray crystallographic measurements on crystals at −100 °C give average C=Se bond le ...
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Isothiouronium
In organic chemistry, isothiouronium is a functional group with the formula [RSC(NH2)2]+ (R = alkyl, aryl) and is the acid salt of isothiourea. The H centres can also be replaced by alkyl and aryl. Structurally, these cations resemble guanidinium cations. The CN2S core is planar and the C–N bonds are short. Synthesis Salts comprising these cations are typically prepared by alkylation of thiourea: :SC(NH2)2 + RX → [RSC(NH2)2]+X− Reactions Hydrolysis of isothiouronium salts gives thiols. :[RSC(NH2)2]+X− + NaOH → RSH + OC(NH2)2 + NaX Isothiouronium salts in which the sulfur has been alkylated, such as ''S''-methylisothiourea hemisulfate (CAS number: 867-44-7), will convert amines into guanidinium groups. This approach is sometimes called the Rathke synthesis after Bernhard Rathke who first reported it in 1881. : RNH2 + [CH3SC(NH2)2]+X− → [CH3N(H)C(NH2)2]+X− + CH3SH Chelating resins with isothiouronium groups are used to recover mercury and other noble metals in ...
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Thiol
In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols (that is, sulfur takes the place of oxygen in the hydroxyl () group of an alcohol), and the word is a blend of "''thio-''" with "alcohol". Many thiols have strong odors resembling that of garlic, cabbage or rotten eggs. Thiols are used as odorants to assist in the detection of natural gas (which in pure form is odorless), and the smell of natural gas is due to the smell of the thiol used as the odorant. Nomenclature Thiols are sometimes referred to as mercaptans () or mercapto compounds, a term introduced in 1832 by William Christopher Zeise and is derived from the Latin ('capturing mercury')''Oxford American Dictionaries'' (Mac OS X Leopard). because the thiolate grou ...
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Carbon
Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 electrons. It belongs to group 14 of the periodic table. Carbon makes up about 0.025 percent of Earth's crust. Three Isotopes of carbon, isotopes occur naturally, carbon-12, C and carbon-13, C being stable, while carbon-14, C is a radionuclide, decaying with a half-life of 5,700 years. Carbon is one of the timeline of chemical element discoveries#Pre-modern and early modern discoveries, few elements known since antiquity. Carbon is the 15th abundance of elements in Earth's crust, most abundant element in the Earth's crust, and the abundance of the chemical elements, fourth most abundant element in the universe by mass after hydrogen, helium, and oxygen. Carbon's abundance, its unique diversity of organic compounds, and its unusual abi ...
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Organic Synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the general subject of organic synthesis, there are many different types of synthetic routes that can be completed including total synthesis, Enantioselective synthesis, stereoselective synthesis, automated synthesis, and many more. Additionally, in understanding organic synthesis it is necessary to be familiar with the methodology, techniques, and applications of the subject. Total synthesis A total synthesis refers to the complete chemical synthesis of molecules from simple, Precursor (chemistry), natural precursors. Total synthesis is accomplished either via a linear or convergent approach. In a Linear synthesis, ''linear'' synthesis—often adequate for simple structures—several steps are performed sequentially until the molecule is com ...
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Hydrogen Peroxide
Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%–6% by weight) in water for consumer use and in higher concentrations for industrial use. Concentrated hydrogen peroxide, or "high-test peroxide", decomposes explosively when heated and has been used as both a monopropellant and an oxidizer in rocketry. Hydrogen peroxide is a reactive oxygen species and the simplest peroxide, a compound having an oxygen–oxygen single bond. It decomposes slowly into water and elemental oxygen when exposed to light, and rapidly in the presence of organic or reactive compounds. It is typically stored with a Stabilizer (chemistry), stabilizer in a weakly acidic solution in an opaque bottle. Hydrogen peroxide is found in biological systems including the human body. Enzymes that u ...
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Carbon Dioxide
Carbon dioxide is a chemical compound with the chemical formula . It is made up of molecules that each have one carbon atom covalent bond, covalently double bonded to two oxygen atoms. It is found in a gas state at room temperature and at normally-encountered concentrations it is odorless. As the source of carbon in the carbon cycle, atmospheric is the primary carbon source for life on Earth. In the air, carbon dioxide is transparent to visible light but absorbs infrared, infrared radiation, acting as a greenhouse gas. Carbon dioxide is soluble in water and is found in groundwater, lakes, ice caps, and seawater. It is a trace gas Carbon dioxide in Earth's atmosphere, in Earth's atmosphere at 421 parts per million (ppm), or about 0.042% (as of May 2022) having risen from pre-industrial levels of 280 ppm or about 0.028%. Burning fossil fuels is the main cause of these increased concentrations, which are the primary cause of climate change.IPCC (2022Summary for pol ...
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Calcium Cyanamide
Calcium cyanamide, also known as Calcium carbondiamide, Calcium cyan-2°-amide or Calcium cyanonitride is the inorganic compound with the formula CaCN2. It is the calcium salt of the cyanamide () anion. This chemical is used as fertilizer and is commercially known as nitrolime. It also has herbicide, herbicidal activity and in the 1950s was marketed as cyanamid. It was first synthesized in 1898 by Adolph Frank and Nikodem Caro (Frank–Caro process). History In their search for a new process for producing cyanides for gold cyanidation, cyanide leaching of gold, Frank and Caro discovered the ability of alkaline earth carbides to absorb atmospheric nitrogen at high temperatures. Fritz Rothe, a colleague of Frank and Caro, succeeded in 1898 in overcoming problems with the use of calcium carbide and clarified that at around 1,100 °C not calcium cyanide but calcium cyanamide is formed in the reaction. In fact, the initial target product sodium cyanide can also be obtained from c ...
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Hydrogen Sulfide
Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is toxic, corrosive, and flammable. Trace amounts in ambient atmosphere have a characteristic foul odor of rotten eggs. Swedish chemist Carl Wilhelm Scheele is credited with having discovered the chemical composition of purified hydrogen sulfide in 1777. Hydrogen sulfide is toxic to humans and most other animals by inhibiting cellular respiration in a manner similar to hydrogen cyanide. When it is inhaled or its salts are ingested in high amounts, damage to organs occurs rapidly with symptoms ranging from breathing difficulties to convulsions and death. Despite this, the human body produces small amounts of this sulfide and its mineral salts, and uses it as a signalling molecule. Hydrogen sulfide is often produced from the microbial breakdown of organic matter in the absence of oxygen, such as in swamps and sewers; this process is commonly known as anaerobic digestio ...
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