In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.
Tetrahedrane is a hypothetical platonic hydrocarbon with chemical formula C4H4 and a tetrahedral structure. The molecule would be subject to considerable angle strain and has not been synthesized as of 2023. However, a number of derivatives have been prepared. In a more general sense, the term tetrahedranes is used to describe a class of molecules and ions with related structure, e.g. white phosphorus.
Cyclobutadiene is an organic compound with the formula C4H4. It is very reactive owing to its tendency to dimerize. Although the parent compound has not been isolated, some substituted derivatives are robust and a single molecule of cyclobutadiene is quite stable. Since the compound degrades by a bimolecular process, the species can be observed by matrix isolation techniques at temperatures below 35 K. It is thought to adopt a rectangular structure.
In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula −C4H9, derived from either of the two isomers (n-butane and isobutane) of butane.
In organic chemistry, a substituent is one or a group of atoms that replaces atoms, thereby becoming a moiety in the resultant (new) molecule.
Heptadecane is an organic compound, an alkane hydrocarbon with the chemical formula C17H36. The name may refer to any of 24894 theoretically possible structural isomers, or to a mixture thereof.
Cyclohexane conformations are any of several three-dimensional shapes adopted by molecules of cyclohexane. Because many compounds feature structurally similar six-membered rings, the structure and dynamics of cyclohexane are important prototypes of a wide range of compounds.
In organic chemistry, ring strain is a type of instability that exists when bonds in a molecule form angles that are abnormal. Strain is most commonly discussed for small rings such as cyclopropanes and cyclobutanes, whose internal angles are substantially smaller than the idealized value of approximately 109°. Because of their high strain, the heat of combustion for these small rings is elevated.
Magic acid is a superacid consisting of a mixture, most commonly in a 1:1 molar ratio, of fluorosulfuric acid and antimony pentafluoride. This conjugate Brønsted–Lewis superacid system was developed in the 1960s by Ronald Gillespie and his team at McMaster University, and has been used by George Olah to stabilise carbocations and hypercoordinated carbonium ions in liquid media. Magic acid and other superacids are also used to catalyze isomerization of saturated hydrocarbons, and have been shown to protonate even weak bases, including methane, xenon, halogens, and molecular hydrogen.
Asymmetric induction describes the preferential formation in a chemical reaction of one enantiomer or diastereoisomer over the other as a result of the influence of a chiral feature present in the substrate, reagent, catalyst or environment. Asymmetric induction is a key element in asymmetric synthesis.
Heat of formation group additivity methods in thermochemistry enable the calculation and prediction of heat of formation of organic compounds based on additivity. This method was pioneered by S. W. Benson.
In organic chemistry, the di-π-methane rearrangement is the photochemical rearrangement of a molecule that contains two π-systems separated by a saturated carbon atom. In the aliphatic case, this molecules is a 1,4-diene; in the aromatic case, an allyl-substituted arene. The reaction forms (respectively) an ene- or aryl-substituted cyclopropane. Formally, it amounts to a 1,2 shift of one ene group or the aryl group, followed by bond formation between the lateral carbons of the non-migrating moiety:
A-values are numerical values used in the determination of the most stable orientation of atoms in a molecule, as well as a general representation of steric bulk. A-values are derived from energy measurements of the different cyclohexane conformations of a monosubstituted cyclohexane chemical. Substituents on a cyclohexane ring prefer to reside in the equatorial position to the axial. The difference in Gibbs free energy (ΔG) between the higher energy conformation and the lower energy conformation is the A-value for that particular substituent.
Triisopropylamine is an organic chemical compound consisting of three isopropyl groups bound to a central nitrogen atom. As a hindered tertiary amine, it can be used as a non-nucleophilic base and as a stabilizer for polymers; however, its applications are limited by its relatively high cost and difficult synthesis.
2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol or tri-tert-butylcarbinol is an organic compound with formula C13H28O, ((H3C)3C)3COH, or tBu3COH. It is an alcohol that can be viewed as a structural analog of a tridecane isomer (2,2,4,4-tetramethyl-3-t-butylpentane) where the central hydrogen has been replaced by a hydroxyl group -OH.
Tetra-tert-butylethylene is a hypothetical organic compound, a hydrocarbon with formula C18H36, or ((H3C−)3C−)2C=C(−C(−CH3)3)2. As the name indicates, its molecular structure can be viewed as an ethylene molecule H2C=CH2 with the four hydrogens replaced by tert-butyl −C(−CH3)3 groups.
Radical disproportionation encompasses a group of reactions in organic chemistry in which two radicals react to form two different non-radical products. Radicals in chemistry are defined as reactive atoms or molecules that contain an unpaired electron or electrons in an open shell. The unpaired electrons can cause radicals to be unstable and reactive. Reactions in radical chemistry can generate both radical and non-radical products. Radical disproportionation reactions can occur with many radicals in solution and in the gas phase. Due to the reactive nature of radical molecules, disproportionation proceeds rapidly and requires little to no activation energy. The most thoroughly studied radical disproportionation reactions have been conducted with alkyl radicals, but there are many organic molecules that can exhibit more complex, multi-step disproportionation reactions.
The White–Chen catalyst is an Iron-based coordination complex named after Professor M. Christina White and her graduate student Mark S. Chen. The catalyst is used along with hydrogen peroxide and acetic acid additive to oxidize aliphatic sp3 C-H bonds in organic synthesis. The catalyst is the first to allow for preparative and predictable aliphatic C–H oxidations over a broad range of organic substrates. Oxidations with the catalyst have proven to be remarkably predictable based on sterics, electronics, and stereoelectronics allowing for aliphatic C–H bonds to be thought of as a functional group in the streamlining of organic synthesis.
An N-Heterocyclic silylene (NHSi) is an uncharged heterocyclic chemical compound consisting of a divalent silicon atom bonded to two nitrogen atoms. The isolation of the first stable NHSi, also the first stable dicoordinate silicon compound, was reported in 1994 by Michael Denk and Robert West three years after Anthony Arduengo first isolated an N-heterocyclic carbene, the lighter congener of NHSis. Since their first isolation, NHSis have been synthesized and studied with both saturated and unsaturated central rings ranging in size from 4 to 6 atoms. The stability of NHSis, especially 6π aromatic unsaturated five-membered examples, make them useful systems to study the structure and reactivity of silylenes and low-valent main group elements in general. Though not used outside of academic settings, complexes containing NHSis are known to be competent catalysts for industrially important reactions. This article focuses on the properties and reactivity of five-membered NHSis.
Pnictogen-substituted tetrahedranes are pnictogen-containing analogues of tetrahedranes with the formula RxCxPn4-x. Computational work has indicated that the incorporation of pnictogens to the tetrahedral core alleviates the ring strain of tetrahedrane. Although theoretical work on pnictogen-substituted tetrahedranes has existed for decades, only the phosphorus-containing species have been synthesized. These species exhibit novel reactivities, most often through ring-opening and polymerization pathways. Phosphatetrahedranes are of interest as new retrons for organophosphorus chemistry. Their strain also make them of interest in the development of energy-dense compounds.
