Dianin's compound

Dianin's compound
Names
IUPAC name
4-(2,2,4-Trimethyl-4-chromanyl)phenol
Other names
4-p-Hydroxyphenyl-2,2,4-trimethylchroman
Identifiers
CAS Number
  • 472-41-3 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 88264 checkY
ECHA InfoCard 100.006.775 Edit this at Wikidata
PubChem CID
  • 97788
UNII
  • 90766708Z6 checkY
CompTox Dashboard (EPA)
  • DTXSID30883388 Edit this at Wikidata
InChI
  • InChI=1S/C18H20O2/c1-17(2)12-18(3,13-8-10-14(19)11-9-13)15-6-4-5-7-16(15)20-17/h4-11,19H,12H2,1-3H3 checkY
    Key: KXYDGGNWZUHESZ-UHFFFAOYSA-N checkY
  • InChI=1/C18H20O2/c1-17(2)12-18(3,13-8-10-14(19)11-9-13)15-6-4-5-7-16(15)20-17/h4-11,19H,12H2,1-3H3
    Key: KXYDGGNWZUHESZ-UHFFFAOYAP
  • CC1(CC(C2=CC=CC=C2O1)(C)C3=CC=C(C=C3)O)C
  • Oc1ccc(cc1)C2(c3c(OC(C2)(C)C)cccc3)C
Properties
Chemical formula
 C18H20O2
Molar mass 268.35 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Dianin's compound (4-p-hydroxyphenyl-2,2,4-trimethylchroman) was first prepared by Aleksandr Dianin in 1914.[1] This compound is a condensation isomer of bisphenol A and acetone and of special importance in host–guest chemistry because it can form a large variety of clathrates with suitable guest molecules. One example is the clathrate of Dianin's compound with morpholine.[2] Slow evaporation of a solution containing both organic compounds yields crystals. Each asymmetric unit cell making up the crystal contains six chroman molecules of which two are deprotonated and two protonated morpholine molecules. The six chroman molecules are racemate pairs.

References

  1. ^ Dianin, A. P. (1914). "Condensation of phenol with unsaturated ketones. Condensation of phenol with mesityl oxide". Zhurnal Russkago Fiziko-Khimicheskago Obshchestva (J. Russ. Phys. Chem. Soc.) (in Russian). 36: 1310–1319.
  2. ^ Lloyd, Gareth O.; Bredenkamp, Martin W.; Barbour, Leonard J. (2005). "Enclathration of morpholinium cations by Dianin's compound: Salt formation by partial host-to-guest proton transfer". Chemical Communications. 2005 (32): 4053–4055. doi:10.1039/b507726e. PMID 16091797.