Crystal engineered acid-base complexes with 2D and 3D hydrogen bonding systems using a bisphosphonic acid as the building block Academic Article uri icon


  • The phosphonic acid iminobis(methylene phosphonic acid), NDP, [NH 2(CH 2PO 3H) 2][H 3O], exists as a zwitterion and can act as both a hydrogen bond donor and acceptor. NDP synthon was reacted with three organic bases, 2,2-bipyridine, 4,4-trimethylene-dipyridine, and a hexaazamacrocyclic crown ether, to construct highly stable hydrogen bonded structures. The 2,2-bipyridine complex 2 is layered, the layers being formed through hydrogen bonding of the phosphonic acid groups. The layers are largely formed by strong PO-H -O-P type hydrogen bonds (2.49-2.62 ) with the protonated bipyridyls held between the layers by strong NH +O- P hydrogen bonds. In complex 3, each amino-nitrogen atom is protonated leaving each phosphonic acid group negatively charged. The NDP molecules align in hydrogen bonded rows in which the molecules are bonded together by quadruple hydrogen bonds: two P-O -HO-P and two NH 2+O-P. The rows are then connected to each other by the NH 2+O-P hydrogen bonds between the pyridyl and the phosphonic acid groups. In compound 4, the azacrown ether ring encloses two NDP molecules with four such entities arranged in the unit cell according to the P2 1/n symmetry. There are 14 water molecules per ring filling the voids between the rings creating a three-dimensional hydrogen bonding network. 2005 American Chemical Society.

published proceedings


author list (cited authors)

  • Kong, D. Y., McBee, J. L., & Clearfield, A.

citation count

  • 28

complete list of authors

  • Kong, DY||McBee, JL||Clearfield, A

publication date

  • December 2005