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Attempted cocrystallisation yields hydrogen-bonded salts of β-diketones (CROSBI ID 559883)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija

Judaš, Nenad ; Friščić, Tomislav, Jones, Bill Attempted cocrystallisation yields hydrogen-bonded salts of β-diketones // 44th Annual Midwest Regional Meeting of the American Chemical Society, Book of abstracts. 2009

Podaci o odgovornosti

Judaš, Nenad ; Friščić, Tomislav, Jones, Bill

engleski

Attempted cocrystallisation yields hydrogen-bonded salts of β-diketones

The atempt to use liquid-assisted grinding (LAG)[Friščić, T. ; Jones, W. Cryst. Growth Des. 2009 9 1621-1637] to prepare the Co(dbm)2(tmo)2 complex from CoO, dibenzoylmethane (Hdbm) and thiomorpholine (tmo) failed. Instead, powder diffraction (PXRD) indicated that a new organic phase was obtained. The experiment was repeated without CoO and in several Hdbm to tmo stoichiometry ratios. PXRD patterns and thermal analysis confirmed that the product consists of Hdbm and tmo in a 1 : 1 stoichiometric ratio. Although the product was soluble in various organic solvents it was not possible to re-crystallise it, as pure Hdbm was repeatedly obtained. Subsequently, single crystals were obtained from a solution in liquid tmo. LAG screening of mechanochemical reactivity revealed that Hdbm also readily forms new materials with secondary amines: morpholine (mor), piperidine (pip) and 2, 6-dimethylpiperidine (26Mepip). The use of these liquids as solvents provided single crystals of (Hdbm)•(mor), (Hdbm)•(pip) and (Hdbm)•(26Mepip). Single crystal X-ray diffraction revealed that, in each case, the solid phase was built up of discrete hydrogen-bonded ionic assemblies of the type [2 anion • 2 cation] (Figs. 1 and 2). The fact that dbm- anions are present in the solid phase is surprising considering the well-known stability of the chelate 6-membered ring in β-diketones.[Bertolasi, V. ; Gilli, P. ; Ferretti, V. ; Gilli, G. J. Am. Chem. Soc. 1991 113 4917-4925] The crystal structures of (Hdbm)•(tmo), (Hdbm)•(mor), (Hdbm)•(pip) and (Hdbm)•(26Mepip) are the first examples of β-diketonate anions present in the crystal phase as non-coordinated anionic moieties. Analogous experiments were performed with benzoylacetone and acetylacetone.

liquid-assisted grinding; hydrogen bonded beta-diketonate salts

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Podaci o prilogu

2009.

objavljeno

Podaci o matičnoj publikaciji

44th Annual Midwest Regional Meeting of the American Chemical Society, Book of abstracts

Podaci o skupu

44th Annual Midwest Regional Meeting of the American Chemical Society

poster

21.10.2009-24.10.2009

Iowa City (IA), Sjedinjene Američke Države

Povezanost rada

Kemija