Carbamoyl
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Carbamoyl
Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula . It can be obtained by the reaction of ammonia and carbon dioxide at very low temperatures, which also yields an equal amount of ammonium carbamate . The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH.J. B. Bossa, P. Theulé, F. Duvernay, F. Borget and T. Chiavassa (2008): "Carbamic acid and carbamate formation in NH3:CO2 ices – UV irradiation versus thermal processes". ''Astronomy and Astrophysics'', volume 492, issue 3, pages 719-724. Carbamic acid could be seen as both an amine and carboxylic acid, and therefore an amino acid;R. K. Khanna and M. H. Moore (1999): "Carbamic acid: molecular structure and IR spectra". ''Spectrochimica Acta Part A: M ...
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Carbamoyl Chloride
A carbamoyl chloride is the functional group with the formula R2NC(O)Cl. The parent carbamoyl chloride, H2NCOCl is unstable, but many N-substituted analogues are known. Most examples are moisture sensitive, colourless, and soluble in nonpolar organic solvents. An example is dimethylcarbamoyl chloride (m.p. −90 °C and b.p. 93 °C). Carbamoyl chlorides are used to prepare a number of pesticides, e.g. carbofuran and aldicarb. Production and examples Carbamoyl chlorides are prepared by the reaction of an amine with phosgene: :2 R2NH + COCl2 → R2NCOCl + 2NH2l They also arise by the addition of hydrogen chloride to isocyanates: :RNCO + HCl → RNHCOCl In this way, carbamonyl chlorides can be prepared with N-H functionality. Reactions In a reaction that is typically avoided, hydrolysis of carbamoyl chlorides gives carbamic acids: :R2NCOCl + H2O → R2NC(O)OH + HCl Owing to the influence of the amino group, these compounds are less hydrolytically sensitive than the usual acid chlo ...
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Ammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous waste, particularly among aquatic organisms, and it contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to 45% of the world's food and fertilizers. Around 70% of ammonia is used to make fertilisers in various forms and composition, such as urea and Diammonium phosphate. Ammonia in pure form is also applied directly into the soil. Ammonia, either directly or indirectly, is also a building block for the synthesis of many pharmaceutical products and is used in many commercial cleaning products. It is mainly collected by downward displacement of both air and water. Although common in nature—both terrestrially and in the outer planets of the Solar System—and in wide use, ammonia is both caust ...
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Ammonium Carbamate
Ammonium carbamate is a chemical compound with the formula consisting of ammonium cation and carbamate anion . It is a white solid that is extremely soluble in water, less so in alcohol. Ammonium carbamate can be formed by the reaction of ammonia with carbon dioxide , and will slowly decompose to those gases at ordinary temperatures and pressures. It is an intermediate in the industrial synthesis of urea , an important fertilizer. Properties Solid-gas equilibrium In a closed container solid ammonium carbamate is in equilibrium with carbon dioxide and ammonia R. N. Bennett, P. D. Ritchie, D. Roxburgh and J. Thomson (1953): "The system ammonia + carbon dioxide + ammonium carbamate. Part I. — The equilibrium of thermal dissociation of ammonium carbamate". ''Transactions of the Faraday Society'', volume 49, pages 925-929. : Lower temperatures shift the equilibrium towards the carbamate. At higher temperatures ammonium carbamate condenses into urea: : This reaction was firs ...
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Functional Group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. Fun ...
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Carbamate
In organic chemistry, a carbamate is a category of organic compounds with the general formula and structure , which are formally derived from carbamic acid (). The term includes organic compounds (e.g., the ester ethyl carbamate), formally obtained by replacing one or more of the hydrogen atoms by other organic functional groups; as well as salts with the carbamate anion (e.g. ammonium carbamate). Polymers whose units are joined by carbamate groups are an important family of plastics, the polyurethanes. Properties While carbamic acids are unstable, many carbamate esters or ionic) are stable and well known. Equilibrium with carbonate and bicarbonate In water solutions, the carbamate anion slowly equilibrates with the ammonium cation and the carbonate or bicarbonate anions: : : Calcium carbamate is soluble in water, whereas calcium carbonate is not. Adding a calcium salt to an ammonium carbamate/carbonate solution will precipitate some calcium carbonate immediatel ...
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International Union Of Pure And Applied Chemistry
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is a member of the International Science Council (ISC). IUPAC is registered in Zürich, Switzerland, and the administrative office, known as the "IUPAC Secretariat", is in Research Triangle Park, North Carolina, United States. This administrative office is headed by IUPAC's executive director, currently Lynn Soby. IUPAC was established in 1919 as the successor of the International Congress of Applied Chemistry for the advancement of chemistry. Its members, the National Adhering Organizations, can be national chemistry societies, national academies of sciences, or other bodies representing chemists. There are fifty-four National Adhering Organizations and three Associate National Adhering Organizations. IUPAC's Inter-divisional Committee on ...
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Glycine
Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid (carbamic acid is unstable), with the chemical formula NH2‐ CH2‐ COOH. Glycine is one of the proteinogenic amino acids. It is encoded by all the codons starting with GG (GGU, GGC, GGA, GGG). Glycine is integral to the formation of alpha-helices in secondary protein structure due to its compact form. For the same reason, it is the most abundant amino acid in collagen triple-helices. Glycine is also an inhibitory neurotransmitter – interference with its release within the spinal cord (such as during a ''Clostridium tetani'' infection) can cause spastic paralysis due to uninhibited muscle contraction. It is the only achiral proteinogenic amino acid. It can fit into hydrophilic or hydrophobic environments, due to its minimal side chain of only one hydrogen atom. History and etymology Glycine was discovered in 1820 by the French chemist He ...
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Proton
A proton is a stable subatomic particle, symbol , H+, or 1H+ with a positive electric charge of +1 ''e'' elementary charge. Its mass is slightly less than that of a neutron and 1,836 times the mass of an electron (the proton–electron mass ratio). Protons and neutrons, each with masses of approximately one atomic mass unit, are jointly referred to as "nucleons" (particles present in atomic nuclei). One or more protons are present in the nucleus of every atom. They provide the attractive electrostatic central force which binds the atomic electrons. The number of protons in the nucleus is the defining property of an element, and is referred to as the atomic number (represented by the symbol ''Z''). Since each element has a unique number of protons, each element has its own unique atomic number, which determines the number of atomic electrons and consequently the chemical characteristics of the element. The word ''proton'' is Greek for "first", and this name was given to the ...
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Zwitterionic
In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively- and negatively-charged functional groups. : With amino acids, for example, in solution a chemical equilibrium will be established between the "parent" molecule and the zwitterion. Betaines are zwitterions that cannot isomerize to an all-neutral form, such as when the positive charge is located on a quaternary ammonium group. Similarly, a molecule containing a phosphonium group and a carboxylate group cannot isomerize. Amino acids The equilibrium is established in two stages. In the first stage, a proton is transferred from the carboxyl group to a water molecule: :H2N(R)CO2H + H2O H2N(R)CO2- + H3O+ In the second stage, a proton is transferred from the hydronium ion to the amine group: :H2N(R)CO2- + H3O+ H3N+ (R)CO2- + H2O Overall, the reaction is an isomerization reaction :H2N(R)CO2H H3N+ (R)CO2- The ratio of the concentrations of the two spec ...
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Ammonium
The ammonium cation is a positively-charged polyatomic ion with the chemical formula or . It is formed by the protonation of ammonia (). Ammonium is also a general name for positively charged or protonated substituted amines and quaternary ammonium cations (), where one or more hydrogen atoms are replaced by organic groups (indicated by R). Acid–base properties The ammonium ion is generated when ammonia, a weak base, reacts with Brønsted acids (proton donors): :H+ + NH3 -> H4 The ammonium ion is mildly acidic, reacting with Brønsted bases to return to the uncharged ammonia molecule: : H4 + B- -> HB + NH3 Thus, treatment of concentrated solutions of ammonium salts with strong base gives ammonia. When ammonia is dissolved in water, a tiny amount of it converts to ammonium ions: :H2O + NH3 OH- + H4 The degree to which ammonia forms the ammonium ion depends on the pH of the solution. If the pH is low, the equilibrium shifts to the right: more ammonia molecules are co ...
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Protonation
In chemistry, protonation (or hydronation) is the adding of a proton (or hydron, or hydrogen cation), (H+) to an atom, molecule, or ion, forming a conjugate acid. (The complementary process, when a proton is removed from a Brønsted–Lowry acid, is deprotonation.) Some examples include *The protonation of water by sulfuric acid: *:H2SO4 + H2O H3O+ + *The protonation of isobutene in the formation of a carbocation: *:(CH3)2C=CH2 + HBF4 (CH3)3C+ + *The protonation of ammonia in the formation of ammonium chloride from ammonia and hydrogen chloride: *:NH3( g) + HCl( g) → NH4Cl( s) Protonation is a fundamental chemical reaction and is a step in many stoichiometric and catalytic processes. Some ions and molecules can undergo more than one protonation and are labeled polybasic, which is true of many biological macromolecules. Protonation and deprotonation (removal of a proton) occur in most acid–base reactions; they are the core of most acid–base reaction theories. A Brønst ...
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Methyl Carbamate
Methyl carbamate (also called methylurethane, or urethylane) is an organic compound and the simplest ester of carbamic acid (H2NCO2H). It is a colourless solid. Methyl carbamate is prepared by the reaction of methanol and urea: :CO(NH2)2 + CH3OH → CH3OC(O)NH2 + NH3 It also forms in the reaction of ammonia with methyl chloroformate or dimethyl carbonate. Safety and occurrence Unlike its close relative ethyl carbamate it is not mutagenic in ''Salmonella'' (it tested negative in the Ames test), but it is mutagenic in ''Drosophila''. Experimental evidence does show that it is a carcinogen in rats, and not carcinogenic in mice. The compound is "known to the state of California to cause cancer" per Proposition 65. Production, use, and exposure The compound was detected in wines preserved with dimethyl dicarbonate. Methyl carbamate is used primarily in the textile and polymer industries as a reactive intermediate. In the textile industry, it is used in the manufacture of ...
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