Dario Braga, Lucia Maini, Giorgiana de Sanctis, Katia Rubini, Fabrizia Grepioni, Michele R. Chierotti and Roberto Gobetto Mechanochemical Preparation of Hydrogen-Bonded Adducts Between the Diamine 1,4-Diazabicyclo[2.2.2]octane and Dicarboxylic Acids of Variable Chain Length: An X-ray Diffraction and Solid-State NMR Study Chemistry - A European Journal 9
Mechanical mixing of solid dicarboxylic acids of variable chain length HOOC(CH2)nCOOH (n = 1–7) with solid 1,4-diazabicyclo[2.2.2]octane affords salts or co-crystals of the formula [N(CH2CH2)3N]-H-[OOC(CH2)nCOOH] (n = 1–7). The process is schematically depicted here. The products have been compared with the corresponding salts prepared from solution. The carbon chemical shift tensors of the COOH group obtained from the sideband intensity of low speed spinning NMR spectra provide a reliable criterion for characterization of the hydrogen-bonding interactions.
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