1,3,5,7-Adamantanetetracarboxylic acid

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
CAS Number	100884-80-8;
3D model (JSmol)	Interactive image;
Abbreviations	ADTA
ChemSpider	540862;
PubChem CID	622495;
CompTox Dashboard (EPA)	DTXSID80347521 ;
	InChI 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;
	SMILES C1C2(CC3(CC1(CC(C2)(C3)C(=O)O)C(=O)O)C(=O)O)C(=O)O;
Properties
Chemical formula	C14H16O8
Molar mass	312.274 g·mol−1
Appearance	colorless crystalline solid
Melting point	395 °C (743 °F; 668 K)
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). Infobox references

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

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 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]

References

^ "Adamantane-1,3,5,7-tetracarboxylic acid". PubChem. Retrieved 18 January 2024.
^ "1,3,5,7-Adamantanetetracarboxylic acid". ChemSpider. Retrieved 18 January 2024.
^ ^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.
^ ^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.
^ 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.

[pubchem-1] "Adamantane-1,3,5,7-tetracarboxylic acid". PubChem. Retrieved 18 January 2024.

[chemspider-2] "1,3,5,7-Adamantanetetracarboxylic acid". ChemSpider. Retrieved 18 January 2024.

[Newkome-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.

[Li_HOF_review-4] 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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