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Trimesic acid

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Trimesic acid
Skeletal formula
Ball-and-stick model
Names
IUPAC name benzene-1,3,5-tricarboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.008.253 Edit this at Wikidata
EC Number
  • 209-077-7
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11)(H,12,13)(H,14,15)Key: QMKYBPDZANOJGF-UHFFFAOYSA-N
  • InChI=1/C9H6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11)(H,12,13)(H,14,15)Key: QMKYBPDZANOJGF-UHFFFAOYAC
SMILES
  • c1c(cc(cc1C(=O)O)C(=O)O)C(=O)O
Properties
Chemical formula C9H6O6
Molar mass 210.14034
Acidity (pKa) 3.12, 3.89, 4.70
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

Trimesic acid, formally known as benzene-1,3,5-tricarboxylic acid, is a benzene derivative with three carboxylic acid groups.

Trimesic acid is a planar molecule (and is one of only four benzenecarboxylic acids with that property).

Trimesic acid can be combined with para-hydroxypyridine to make a water-based gel, stable up to 95 °C.

Trimesic acid crystallizes from water in a hydrogen-bonded hydrated network with wide unidimensional empty channels.

See also

References

  1. Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.
  2. ZORAN MARKOVIĆ, DALIBOR BADJUK and IVAN GUTMAN (2004), Geometry and conformations of benzenecarboxylic acids. J. Serb. Chem. Soc. volume 69 issue 11, pages 877–882 (paper JSCS 3214), UDC 547.584/.585:539.193:54.02
  3. Li Ming Tang and Yu Jiang Wang (2009), Highly stable supramolecular hydrogels formed from 1,3,5-benzenetricarboxylic acid and hydroxyl pyridines. Chinese Chemical Letters volume 20, issue 10, pp. 1259–1262. doi:10.1016/j.cclet.2009.04.030
  4. F.H. Herbstein (1987), Structural Parsimony and Structural Variety Among Inclusion Complexes, Top. Curr. Chem., volume 140, p. 107


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