Isoindole

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Isoindole
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2H-Isoindole
Identifiers
270-68-8 YesY
ChEBI CHEBI:33179 YesY
ChemSpider 2282425 YesY
Jmol-3D images Image
PubChem 3013853
Properties
C8H7N
Molar mass 117.15 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
Infobox references

Isoindole in heterocyclic chemistry is a benzo-fused pyrrole.[1] The compound is an isomer of indole and its reduced form is an isoindoline. Isoindoles are building blocks for phthalocyanines which are relevant as dyes. Some alkaloids containing isoindole have been isolated and characterized.[2]

Tautomerism[edit]

In solution, the 2H-isoindole tautomer is the predominant form and therefore the compound resembles a pyrrole more than a simple imine.[3] The degree to which the 2H predominates depends on the solvent, and can vary with the substituent in substituted isoindoles.[4]

2H-Isoindole (right) is the predominant tautomer relative to 1H-isoindole (left)

Isoindole-1,3-diones and related derivatives[edit]

The commercially important phthalimide is an isoindole-1,3-dione with two carbonyl groups attached to the heterocyclic ring.

See also[edit]

References[edit]

  1. ^ Gilchrist, T. L. (1987). Heterocyclic Chemistry. Longman. ISBN 0-582-01422-0. 
  2. ^ See for example: Zhang, X.; Ye, W.; Zhao, S.; Che, C. T. (2004). "Isoquinoline and isoindole alkaloids from Menispermum dauricum". Phytochemistry 65 (7): 929–932. doi:10.1016/j.phytochem.2003.12.004. PMID 15081297.  edit
  3. ^ Alan R. Katritzky, Christopher A. Ramsden, J. Joule, Viktor V. Zhdankin (2010). Handbook of Heterocyclic Chemistry. Elsevier. p. 133. 
  4. ^ John A. Joule, Keith Mills (2010). Heterocyclic Chemistry. John Wiley & Sons. p. 447.