Bis(glycinium) oxalate: evidence of strong hydrogen bonding

Abstract

In the title 2:1 salt, 2C(2)H(6)NO(2)(+)center dot C2O42-, the glycine mol-ecule is in the cationic form with a positively charged amino group and an uncharged carboxylic acid group. The doubly charged oxalate anion lies across a crystallographic inversion centre. One of the reasons why the 1:1 glycinium oxalate salt has a higher melting point than the title compound may be the difference in their hydrogen-bonding patterns. A database search for salts formed between amino acids or substituted amino acids and oxalic acid revealed that, in most of the structures, the conformation about the O=C-OH bond is synplanar. D-Tryptophan oxalate is the only example where the OH group of a semi-oxalate adopts an anti-planar conformation. The 2:1 stoichiometry seen in the present salt is observed only in the salts of DL-serine, DL-aspartic acid and betaine with oxalic acid