1,3,5,7-Adamantanetetracarboxylic acid

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1,3,5,7-Adamantanetetracarboxylic acid [1] [2]
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Names
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)
AbbreviationsADTA
ChemSpider
PubChem CID
  • InChI=1S/C14H16O8/c15-7(16)11-1-12(8(17)18)4-13(2-11,9(19)20)6-14(3-11,5-12)10(21)22/h1-6H2,(H,15,16)(H,17,18)(H,19,20)(H,21,22)
    Key: VWAIZPYLEYEEFK-UHFFFAOYSA-N
  • C1C2(CC3(CC1(CC(C2)(C3)C(=O)O)C(=O)O)C(=O)O)C(=O)O
Properties
C14H16O8
Molar mass 312.274 g·mol−1
Appearancecolorless 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]

Contents

Preparation

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]

Uses

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]

Related Research Articles

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.

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<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

<span class="mw-page-title-main">Imide</span> Class of chemical compounds

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<span class="mw-page-title-main">Adamantane</span> Molecule with three connected cyclohexane rings arranged in the "armchair" configuration

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.

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<span class="mw-page-title-main">Supramolecular assembly</span> Complex of molecules non-covalently bound together

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<span class="mw-page-title-main">Trimethylsilyl group</span> Functional group

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.

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<span class="mw-page-title-main">Tetrahedral molecular geometry</span> Central atom with four substituents located at the corners of a tetrahedron

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(−13) = 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.

<span class="mw-page-title-main">Dakin oxidation</span> Organic redox reaction that converts hydroxyphenyl aldehydes or ketones into benzenediols

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.

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<span class="mw-page-title-main">Silsesquioxane</span> Molecular compound with applications in ceramics

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.

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<span class="mw-page-title-main">Rylene dye</span> Dye based on the rylene framework of naphthalene units

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.

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<span class="mw-page-title-main">Diamantane</span> Chemical compound

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.

<span class="mw-page-title-main">Carbon nanothread</span>

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<span class="mw-page-title-main">Hydrogen-bonded organic framework</span>

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.

References

  1. "Adamantane-1,3,5,7-tetracarboxylic acid". PubChem . Retrieved 18 January 2024.
  2. "1,3,5,7-Adamantanetetracarboxylic acid". ChemSpider . Retrieved 18 January 2024.
  3. 1 2 3 Newkome, George R.; Nayak, Ashutosh; Behera, Rajani K.; Moorefield, Charles N.; Baker, Gregory R. (1992). "Chemistry of micelles series. 22. Cascade polymers: synthesis and characterization of four-directional spherical dendritic macromolecules based on adamantane". Journal of Organic Chemistry . 57 (1): 358–362. doi:10.1021/jo00027a061.
  4. 1 2 3 Li, Penghao; Ryder, Matthew R.; Stoddart, J. Fraser (2020). "Hydrogen-Bonded Organic Frameworks: A Rising Class of Porous Molecular Materials". Accounts of Materials Research . 1 (1): 77–87. doi:10.1021/accountsmr.0c00019.
  5. Ermer, Otto (1988). "Five-fold diamond structure of adamantane-1,3,5,7-tetracarboxylic acid". Journal of the American Chemical Society . 110 (12): 3747–3754. doi:10.1021/ja00220a005.