1,3,5,7-Adamantanetetracarboxylic acid

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1,3,5,7-Adamantanetetracarboxylic acid[1][2]
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)
Abbreviations ADTA
ChemSpider
  • 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
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]

Preparation[edit]

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[edit]

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]

References[edit]

  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. ^ a b c 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. ^ a b c 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.
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