A. Batsanov, J. L. Hesselink
2002
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Journal
Acta Crystallographica Section E-structure Reports Online
Abstract
Various stereoisomers of 5,6-dicarboxylic acids with a 2-norbornene or 7-oxanorbornene core, and their norbornane analogues, are easily accessible through the Diels±Alder reaction (Diels & Alder, 1928; Alder & Stein, 1933). The crystal structure of 2-norbornene-(or bicyclo[2.2.1]hept-2ene-)-endo-cis-5,6-dicarboxylic acid has been determined repeatedly by Avitabile et al. (1973), P ̄uger et al. (1973) and, at low temperature, by Bolte et al. (2000). This isomer has also been structurally characterized as a mono-anion, in its potassium salt sesquihydrate (Cser & Sasvari, 1976), and as a ligand in Mn and Co complexes (Hartung et al., 1993; Devereux et al., 1995). However, to our knowledge, no other acid of this class (without additional substituents on the bicyclic core) has been structurally studied in the neutral form, and there is only one structure of a complex, with the norbornane-endo-cis-2,3-dicarboxylic acid ligand (Geraghty et al., 1999). Since these acids are of interest as model compounds for organic additives to in ̄uence the crystal growth of CaCO3 (Megson, 1997; Feast et al., 2002), we undertook a systematic study of their structures.