title: Solid-state tautomerism in 2-carboxyindan-1,3-dione.
abstract: The structure of 2-carboxyindan-1,3-dione was investigated using a combination of quantum-chemical calculations and solid-state NMR and IR spectroscopy. Due to poor solubility of the compound in different solvents, no single crystals could be obtained. Two dimeric structures formed from the tautomers of 2-carboxyindan-1,3-dione are likely to coexist in the solid state. The dimers interconvert via intramolecular proton transfer in one of the tautomeric forms constituting the dimers. The energy barrier of the intramolecular proton transfer reaction is calculated as 5.82 kcal mol(-1) at the MP2/6-31++G level of theory.
authors.affiliation: Institute of Organic Chemistry, Bulgarian Academy of Sciences, 1113 Sofia, Bulgaria. venelin@orgchm.bas.bg
authors.forename: Venelin
authors.initials: V
authors.lastname: Enchev
authors.forename: Silvia
authors.initials: S
authors.lastname: Angelova
authors.forename: Marin
authors.initials: M
authors.lastname: Rogojerov
authors.forename: Valentin
authors.initials: V
authors.lastname: Monev
authors.forename: Iwona
authors.initials: I
authors.lastname: Wawer
authors.forename: Michał
authors.initials: M
authors.lastname: Tkaczyk
authors.forename: Kalina
authors.initials: K
authors.lastname: Kostova
mesh_terms: D019281:Dimerization; D006860:Hydrogen Bonding; D007189:Indans / Q000737:chemistry*; D007536:Isomerism; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D011522:Protons; D013055:Spectrophotometry, Infrared; D013816:Thermodynamics
chemical_list: C558819:2-carboxyindan-1,3-dione; D007189:Indans; D007659:Ketones; D011522:Protons