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Bredt's Rule
Bredt's rule is an empirical observation in organic chemistry that states that a double bond cannot be placed at the bridgehead of a bridged ring system, unless the rings are large enough. The rule is named after Julius Bredt, who first discussed it in 1902 and codified it in 1924. It primarily relates to bridgeheads with carbon-carbon and carbon-nitrogen double bonds. For example, two of the following isomers of norbornene violate Bredt's rule, which makes them too unstable to prepare: In the figure, the bridgehead atoms involved in Bredt's rule violation are highlighted in red. Bredt's rule is a consequence of the fact that having a double bond on a bridgehead, carbons from which three bonds radiate and which the rings share a single covalent bond, would be equivalent to having a trans double bond on a ring, which is not stable for small rings (fewer than eight atoms) due to a combination of ring strain, and angle strain (nonplanar alkene). The p orbitals of the bridgehead ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and 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 and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the 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 in organic chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (included in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Isomers do not necessarily share similar chemical or physical properties. Two main forms of isomerism are structural or constitutional isomerism, in which ''bonds'' between the atoms differ; and stereoisomerism or spatial isomerism, in which the bonds are the same but the ''relative positions'' of the atoms differ. Isomeric relationships form a hierarchy. Two chemicals might be the same constitutional isomer, but upon deeper analysis be stereoisomers of each other. Two molecules that are the same stereoisomer as each other might be in different conformational forms or be different isotopologues. The depth of analysis depends on the field of study or the chemical and physical properties of interest. The English word "isomer" () is a back-for ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tetrahedron (journal)
''Tetrahedron'' is a weekly peer-reviewed scientific journal covering the field of organic chemistry. According to the ''Journal Citation Reports'', ''Tetrahedron'' has a 2020 impact factor of 2.457. ''Tetrahedron'' and Elsevier, its publisher, support an annual symposium. In 2010, complaints were raised over its high subscription cost. Notable papers , the Web of Science lists ten papers from ''Tetrahedron'' that have more than 1000 citations. The four articles that have been cited more than 2000 times are: * – cited 2228 times * – cited 2162 times * – cited 2124 times * – cited 2107 times See also * ''Tetrahedron Letters'' * ''Tetrahedron Computer Methodology'' * ''Polyhedron In geometry, a polyhedron (plural polyhedra or polyhedrons; ) is a three-dimensional shape with flat polygonal faces, straight edges and sharp corners or vertices. A convex polyhedron is the convex hull of finitely many points, not all on th ...'' (journal) Refere ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nature (journal)
''Nature'' is a British weekly scientific journal founded and based in London, England. As a multidisciplinary publication, ''Nature'' features peer-reviewed research from a variety of academic disciplines, mainly in science and technology. It has core editorial offices across the United States, continental Europe, and Asia under the international scientific publishing company Springer Nature. ''Nature'' was one of the world's most cited scientific journals by the Science Edition of the 2019 ''Journal Citation Reports'' (with an ascribed impact factor of 42.778), making it one of the world's most-read and most prestigious academic journals. , it claimed an online readership of about three million unique readers per month. Founded in autumn 1869, ''Nature'' was first circulated by Norman Lockyer and Alexander Macmillan as a public forum for scientific innovations. The mid-20th century facilitated an editorial expansion for the journal; ''Nature'' redoubled its efforts in exp ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
2-quinuclidonium Tetrafluoroborate
Quinuclidones are a class of bicyclic organic compounds with chemical formula C7H11NO with two structural isomers for the base skeleton 3-quinuclidone and 2-quinuclidone. 3-Quinuclidone (1-azabicyclo .2.2ctan-3-one) is an uneventful molecule that can be synthesized as the hydrochloric acid salt in a Dieckman condensation: Organic reduction of this compound gives the compound quinuclidine, structurally related to DABCO, which has one additional bridgehead nitrogen atom. The other isomer, 2-quinuclidone, appears equally uneventful, but in fact it has defied synthesis until 2006. The reason is that this molecule is very unstable because its amide group has the amine lone pair and the carbonyl group not properly aligned, as may be expected for an amide, as a result of steric strain. This behaviour is predicted by Bredt's Rule, and formal amide group resembles in fact an amine, as evidenced by the ease of salt formation. The organic synthesis of the tetrafluoroborate salt of 2-q ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
McGraw-Hill Education
McGraw Hill is an American educational publishing company and one of the "big three" educational publishers that publishes educational content, software, and services for pre-K through postgraduate education. The company also publishes reference and trade publications for the medical, business, and engineering professions. McGraw Hill operates in 28 countries, has about 4,000 employees globally, and offers products and services to about 140 countries in about 60 languages. Formerly a division of The McGraw Hill Companies (later renamed McGraw Hill Financial, now S&P Global), McGraw Hill Education was divested and acquired by Apollo Global Management in March 2013 for $2.4 billion in cash. McGraw Hill was sold in 2021 to Platinum Equity for $4.5 billion. Corporate History McGraw Hill was founded in 1888 when James H. McGraw, co-founder of the company, purchased the ''American Journal of Railway Appliances''. He continued to add further publications, eventually establishing The ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Enolate
In organic chemistry, enolates are organic anions derived from the deprotonation of carbonyl () compounds. Rarely isolated, they are widely used as reagents in the synthesis of organic compounds. Bonding and structure Enolate anions are electronically related to allyl anions. The anionic charge is delocalized over the oxygen and the two carbon sites. Thus they have the character of both an alkoxide and a carbanion. Although they are often drawn as being simple salts, in fact they adopt complicated structures often featuring aggregates. Preparation Deprotonation of enolizable ketones, aromatic alcohols, aldehydes, and esters gives enolates. With strong bases, the deprotonation is quantitative. Typically enolates are generated from using lithium diisopropylamide (LDA). Often, as in conventional Claisen condensations, Mannich reactions, and aldol condensations, enolates are generated in low concentrations with alkoxide bases. Under such conditions, they exist in low concent ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Orbital Hybridisation
In chemistry, orbital hybridisation (or hybridization) is the concept of mixing atomic orbitals to form new ''hybrid orbitals'' (with different energies, shapes, etc., than the component atomic orbitals) suitable for the pairing of electrons to form chemical bonds in valence bond theory. For example, in a carbon atom which forms four single bonds the valence-shell s orbital combines with three valence-shell p orbitals to form four equivalent sp3 mixtures in a tetrahedral arrangement around the carbon to bond to four different atoms. Hybrid orbitals are useful in the explanation of molecular geometry and atomic bonding properties and are symmetrically disposed in space. Usually hybrid orbitals are formed by mixing atomic orbitals of comparable energies. History and uses Chemist Linus Pauling first developed the hybridisation theory in 1931 to explain the structure of simple molecules such as methane (CH4) using atomic orbitals. Pauling pointed out that a carbon atom forms four ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Radical (chemistry)
In chemistry, a radical, also known as a free radical, is an atom, molecule, or ion that has at least one unpaired valence electron. With some exceptions, these unpaired electrons make radicals highly chemically reactive. Many radicals spontaneously dimerize. Most organic radicals have short lifetimes. A notable example of a radical is the hydroxyl radical (HO·), a molecule that has one unpaired electron on the oxygen atom. Two other examples are triplet oxygen and triplet carbene (꞉) which have two unpaired electrons. Radicals may be generated in a number of ways, but typical methods involve redox reactions. Ionizing radiation, heat, electrical discharges, and electrolysis are known to produce radicals. Radicals are intermediates in many chemical reactions, more so than is apparent from the balanced equations. Radicals are important in combustion, atmospheric chemistry, polymerization, plasma chemistry, biochemistry, and many other chemical processes. A majority of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbocation
A carbocation is an ion with a positively charged carbon atom. Among the simplest examples are the methenium , methanium and vinyl cations. Occasionally, carbocations that bear more than one positively charged carbon atom are also encountered (e.g., ethylene dication ). Until the early 1970s, all carbocations were called ''carbonium ions''. In the present-day definition given by the IUPAC, a carbocation is any even-electron cation with significant partial positive charge on a carbon atom. They are further classified in two main categories according to the coordination number of the charged carbon: three in the carbenium ions and five in the carbonium ions. This nomenclature was proposed by G. A. Olah. Carbonium ions, as originally defined by Olah, are characterized by a three-center two-electron delocalized bonding scheme and are essentially synonymous with so-called 'non-classical carbocations', which are carbocations that contain bridging C–C or C–H σ-bonds. Howe ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Reaction Mechanism
In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs. A chemical mechanism is a theoretical conjecture that tries to describe in detail what takes place at each stage of an overall chemical reaction. The detailed steps of a reaction are not observable in most cases. The conjectured mechanism is chosen because it is thermodynamically feasible, and has experimental support in isolated intermediates (see next section) or other quantitative and qualitative characteristics of the reaction. It also describes each reactive intermediate, activated complex, and transition state, and which bonds are broken (and in what order), and which bonds are formed (and in what order). A complete mechanism must also explain the reason for the reactants and catalyst used, the stereochemistry observed in reactants and products, all products formed and the amount of each. The electron or arrow pushing method is often used in i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Elimination Reaction
An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1CB, exists. Finally, the pyrolysis of xanthate and acetate esters proceed through an "internal" elimination mechanism, the Ei mechanism. E2 mechanism The E2 mechanism, where E2 stands for bimolecular elimination, involves a one-step mechanism in which ''carbon-hydrogen'' and ''carbon-halogen'' bonds break to form a double bond (''C=C Pi bond''). The specifics of the reaction are as follows: * E2 is a single step elimination, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
