Diphenic acid

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Diphenic acid
Diphenic Acid Structural Formula V.1.svg
Names
Preferred IUPAC name
[1,1′-Biphenyl]-2,2′-dicarboxylic acid
Other names
2,2'-dibenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.889 Edit this at Wikidata
EC Number
  • 207-576-4
536420
UNII
  • InChI=1S/C14H10O4/c15-13(16)11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(17)18/h1-8H,(H,15,16)(H,17,18)
    Key: GWZCCUDJHOGOSO-UHFFFAOYSA-N
  • C1=CC=C(C(=C1)C2=CC=CC=C2C(=O)O)C(=O)O
Properties
C14H10O4
Molar mass 242.230 g·mol−1
Appearance white solid
Density 1.2917 g/cm3
Melting point 235.5 °C (455.9 °F; 508.6 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diphenic acid is an organic compound with the formula (C6H4CO2H)2. It is the most studied of several isomeric dicarboxylic acids of biphenyl. It is a white solid that can be prepared in the laboratory from anthranilic acid via the diazonium salt.[1] It is the product of the microbial action on phenanthrene.[2]

The compound forms a variety of coordination polymers.[3] It also exhibits atropisomerism.

References[edit]

  1. ^ Atkinson, E. R.; Lawler, H. J. (1927). "Diphenic Acid". Organic Syntheses. 7: 30. doi:10.15227/orgsyn.007.0030.
  2. ^ Moody, J. D.; Freeman, J. P.; Doerge, D. R.; Cerniglia, C. E. (2001). "Degradation of Phenanthrene and Anthracene by Cell Suspensions of Mycobacterium sp. Strain PYR-1". Applied and Environmental Microbiology. 67 (4): 1476–1483. doi:10.1128/AEM.67.4.1476-1483.2001. PMC 92757. PMID 11282593.
  3. ^ Yang, Jin; Ma, Jian-Fang; Liu, Ying-Ying; Ma, Ji-Cheng; Batten, Stuart R. (2009). "A Series of Lead(II) Complexes with π−π Stackings: Structural Diversities by Varying the Ligands". Crystal Growth & Design. 9 (4): 1894–1911. doi:10.1021/cg801085d.