A DATABASE STUDY OF INTERMOLECULAR NH-CENTER-DOT-CENTER-DOT-CENTER-DOT-O HYDROGEN-BONDS FOR CARBOXYLATES, SULFONATES AND MONOHYDROGEN PHOSPHONATES

A search of the Cambridge Structural Database (CSD, version 5.05, 1993 ) was performed in order to compare the geometrical features of the hy drogen bonds involving on the one hand amino groups and on the other h and carboxylates, sulfonates or monohydrogen phosponates. Phosphonates were not considered because only four entries containing amino and ph osphonate moieities were located in the CSD. The hydroxylic group of m onohydrogen phosphonates primarily acts as a hydrogen-bond donor. The three moieties under study show NH...O hydrogen bonds with similar geo metrical features. This statistical analysis has focused on the hydrog en-bond distances and angles and on the distributions of the H atoms a round the acceptor O atoms of carboxylates, sulfonates or monohydrogen phosphonates.