Names | |||
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IUPAC name Adamantane-1,3,5,7-tetracarboxylic acid | |||
Other names 1,3,5,7-Adamantanetetracarboxylic acid Tricyclo[3.3.1.13,7]decane-1,3,5,7-tetracarboxylic acid | |||
Identifiers | |||
3D model (JSmol) | |||
Abbreviations | ADTA | ||
ChemSpider | |||
PubChem CID | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
C14H16O8 | |||
Molar mass | 312.274 g·mol−1 | ||
Appearance | colorless solid [3] | ||
Melting point | 395 °C (743 °F; 668 K) [3] | ||
Related compounds | |||
Related compounds | 1-Adamantanecarboxylic acid | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
1,3,5,7-Adamantanetetracarboxylic acid is an adamantane derivative containing four carboxylic acid groups bonded to each of its four tetrahedral carbon centers. Its tetrahedral symmetry provides applications as a hydrogen-bonded organic framework linker [4] and as a dendrimer core. [3]
In Ermer's 1988 first application of 1,3,5,7-adamantanetetracarboxylic acid as a monomer for a hydrogen-bonded organic framework, [4] it was prepared by alkaline hydrolysis of the corresponding tetraamide, 1,3,5,7-adamantanetetracarboxamide. [5]
1,3,5,7-Adamantanetetracarboxylic acid (abbreviated as the ADTA linker in reticular chemistry) was used in 1988 as one of the first linkers in hydrogen-bonded organic frameworks. A tetrahedral linker, it crystallizes into a five-fold interpenetrated diamond cubic network in which ADTA units are hydrogen-bonded to each other through their carboxylic acid groups. [4]
Cubane is a synthetic hydrocarbon compound with the formula C8H8, and that consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substance, cubane is one of the Platonic hydrocarbons and a member of the prismanes. It was first synthesized in 1964 by Philip Eaton and Thomas Cole. Before this work, Eaton believed that cubane would be impossible to synthesize due to the "required 90 degree bond angles". The cubic shape requires the carbon atoms to adopt an unusually sharp 90° bonding angle, which would be highly strained as compared to the 109.45° angle of a tetrahedral carbon. Once formed, cubane is quite kinetically stable, due to a lack of readily available decomposition paths. It is the simplest hydrocarbon with octahedral symmetry.
Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[AlH4] or LiAlH4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.
In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.
In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. The compounds are structurally related to acid anhydrides, although imides are more resistant to hydrolysis. In terms of commercial applications, imides are best known as components of high-strength polymers, called polyimides. Inorganic imides are also known as solid state or gaseous compounds, and the imido group (=NH) can also act as a ligand.
Adamantane is an organic compound with a formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually stress-free. Adamantane is the most stable isomer of C10H16. The spatial arrangement of carbon atoms in the adamantane molecule is the same as in the diamond crystal. This similarity led to the name adamantane, which is derived from the Greek adamantinos (relating to steel or diamond). It is a white solid with a camphor-like odor. It is the simplest diamondoid.
A tetrahedral intermediate is a reaction intermediate in which the bond arrangement around an initially double-bonded carbon atom has been transformed from trigonal to tetrahedral. Tetrahedral intermediates result from nucleophilic addition to a carbonyl group. The stability of tetrahedral intermediate depends on the ability of the groups attached to the new tetrahedral carbon atom to leave with the negative charge. Tetrahedral intermediates are very significant in organic syntheses and biological systems as a key intermediate in esterification, transesterification, ester hydrolysis, formation and hydrolysis of amides and peptides, hydride reductions, and other chemical reactions.
In organic chemistry, the Ugi reaction is a multi-component reaction involving a ketone or aldehyde, an amine, an isocyanide and a carboxylic acid to form a bis-amide. The reaction is named after Ivar Karl Ugi, who first reported this reaction in 1959.
In chemistry, a supramolecular assembly is a complex of molecules held together by noncovalent bonds. While a supramolecular assembly can be simply composed of two molecules, or a defined number of stoichiometrically interacting molecules within a quaternary complex, it is more often used to denote larger complexes composed of indefinite numbers of molecules that form sphere-, rod-, or sheet-like species. Colloids, liquid crystals, biomolecular condensates, micelles, liposomes and biological membranes are examples of supramolecular assemblies, and their realm of study is known as supramolecular chemistry. The dimensions of supramolecular assemblies can range from nanometers to micrometers. Thus they allow access to nanoscale objects using a bottom-up approach in far fewer steps than a single molecule of similar dimensions.
A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom [−Si(CH3)3], which is in turn bonded to the rest of a molecule. This structural group is characterized by chemical inertness and a large molecular volume, which makes it useful in a number of applications.
Orthocarbonic acid, carbon hydroxide or methanetetrol is the name given to a hypothetical compound with the chemical formula H4CO4 or C(OH)4. Its molecular structure consists of a single carbon atom bonded to four hydroxy groups. It would be therefore a fourfold alcohol. In theory it could lose four protons to give the hypothetical oxocarbon anion orthocarbonateCO4−4, and is therefore considered an oxoacid of carbon.
In a tetrahedral molecular geometry, a central atom is located at the center with four substituents that are located at the corners of a tetrahedron. The bond angles are cos−1(−1⁄3) = 109.4712206...° ≈ 109.5° when all four substituents are the same, as in methane as well as its heavier analogues. Methane and other perfectly symmetrical tetrahedral molecules belong to point group Td, but most tetrahedral molecules have lower symmetry. Tetrahedral molecules can be chiral.
The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H2O2) in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H2O2 is reduced.
The Kulinkovich reaction describes the organic synthesis of substituted cyclopropanols through reaction of esters with dialkyldialkoxytitanium reagents, which are generated in situ from Grignard reagents containing a hydrogen in beta-position and titanium(IV) alkoxides such as titanium isopropoxide. This reaction was first reported by Oleg Kulinkovich and coworkers in 1989.
A silsesquioxane is an organosilicon compound with the chemical formula [RSiO3/2]n. Silsesquioxanes are colorless solids that adopt cage-like or polymeric structures with Si-O-Si linkages and tetrahedral Si vertices. Silsesquioxanes are members of polyoctahedral silsesquioxanes ("POSS"), which have attracted attention as preceramic polymer precursors to ceramic materials and nanocomposites. Diverse substituents (R) can be attached to the Si centers. The molecules are unusual because they feature an inorganic silicate core and an organic exterior. The silica core confers rigidity and thermal stability.
Covalent organic frameworks (COFs) are a class of porous polymers that form two- or three-dimensional structures through reactions between organic precursors resulting in strong, covalent bonds to afford porous, stable, and crystalline materials. COFs emerged as a field from the overarching domain of organic materials as researchers optimized both synthetic control and precursor selection. These improvements to coordination chemistry enabled non-porous and amorphous organic materials such as organic polymers to advance into the construction of porous, crystalline materials with rigid structures that granted exceptional material stability in a wide range of solvents and conditions. Through the development of reticular chemistry, precise synthetic control was achieved and resulted in ordered, nano-porous structures with highly preferential structural orientation and properties which could be synergistically enhanced and amplified. With judicious selection of COF secondary building units (SBUs), or precursors, the final structure could be predetermined, and modified with exceptional control enabling fine-tuning of emergent properties. This level of control facilitates the COF material to be designed, synthesized, and utilized in various applications, many times with metrics on scale or surpassing that of the current state-of-the-art approaches.
A rylene dye is a dye based on the rylene framework of naphthalene units linked in peri-positions. In homologues additional naphthalene units are added, forming compounds — or poly(peri-naphthalene)s — such as perylene, terrylene and quarterrylene.
Barium perchlorate is a powerful oxidizing agent, with the formula Ba(ClO4)2. It is used in the pyrotechnic industry.
Diamantane is an organic compound that is a member of the diamondoids. These are cage hydrocarbons with structures similar to a subunit of the diamond lattice. It is a colorless solid that has been a topic of research since its discovery in oil and separation from deep natural gas condensates. Diamondoids such as diamantane exhibit unusual properties, including low surface energies, high densities, high hydrophobicities, and resistance to oxidation.
A carbon nanothread is a sp3-bonded, one-dimensional carbon crystalline nanomaterial. The tetrahedral sp3-bonding of its carbon is similar to that of diamond. Nanothreads are only a few atoms across, more than 20,000 times thinner than a human hair. They consist of a stiff, strong carbon core surrounded by hydrogen atoms. Carbon nanotubes, although also one-dimensional nanomaterials, in contrast have sp2-carbon bonding as is found in graphite. The smallest carbon nanothread has a diameter of only 0.2 nanometers, much smaller than the diameter of a single-wall carbon nanotube.
Hydrogen-bonded organic frameworks (HOFs) are a class of porous polymers formed by hydrogen bonds among molecular monomer units to afford porosity and structural flexibility. There are diverse hydrogen bonding pair choices that could be used in HOFs construction, including identical or nonidentical hydrogen bonding donors and acceptors. For organic groups acting as hydrogen bonding units, species like carboxylic acid, amide, 2,4-diaminotriazine, and imidazole, etc., are commonly used for the formation of hydrogen bonding interaction. Compared with other organic frameworks, like COF and MOF, the binding force of HOFs is relatively weaker, and the activation of HOFs is more difficult than other frameworks, while the reversibility of hydrogen bonds guarantees a high crystallinity of the materials. Though the stability and pore size expansion of HOFs has potential problems, HOFs still show strong potential for applications in different areas.