The Molecular Structure of 4-Amino 1-Hydroxy Butylidene-1 Bisphosphonic Acid (Ahbbpa); An Uncommon Anhydrous Hydroxybisphosphonic Acid

Abstract

The molecular structure of an anhydrous hydroxybisphosphonic acid was determined by X-ray diffraction techniques and compared to the corresponding hydrated crystalline form. The hydrogen bond network and intermolecular interactions show that the polar bisphosphonic group undergoes a rotation to accomodate a different distribution in the hydrophobic/polar zones observed in the crystal packing, while the rest of the amino side chain connected to the functional carbon atom has identical conformation.

A survey of the behavior of the hydroxybisphosphonic function in crystallized acids, metallic salts, and some related compounds

“…All the compounds, except 24, 25, and 28 (i.e., Ͻ7%) crystallize in centrosymmetric groups with generally a low symmetry group; 27.3% in triclinic (space group 2); 52.3% in monoclinic P1 space group 14 (P2 1 /c, P2 1 /n, P2 1 /a). Only four compounds (2 and 15, Table 1; 24 and 28, Table 2) crystallize in orthorhombic space groups, respectively: Pcab (space group 61), Pbca (s.g. nЊ61), Pca2 1 (space group 29) and Pna2 1 (space group 33). The volume occupied by the ligand HEBP is about 200 Å 3 , and after considering the volume of cations, water molecules, esterification groups, and substitution of the CH 3 group, it can be observed that the compacity is nearly the same for all the compounds.…”

A 1H, 13C, 31P and 15N NMR study of (pyrrolidine‐2,2‐diyl)bisphosphonic acid, tetraalkyl(pyrrolidine‐2,2‐diyl)bisphosphonates and acyclic tetraethyl bisphosphonates

“…Gem-bisphosphonates or gem-bisphosphonic acids can complex well with calcium and magnesium. 1 As a result their use in various areas, for instance in the medical field 2 , as plant growth regulators 3 and in the nuclear industry 2 , has been known for some time. We report here a multinuclear NMR study, in particular nitrogen-15, of new tetraalkyl bisphosphonates in a cyclic series and acyclic forms.…”

Analysis of supramolecular interactions in alendroniate alkali metal salts: synthesis, structure, and properties of novel sodium alendronate polymorph

“…… O bonds are dominant and cover the total HS area in the range from 41.6% in rubidium salt (PUQHOA) [14] to 70.6% in alendronic acid (GOWZEX) [17]. On the other hand, subtle interactions such as H … H are also significant contributors, associating from 22.2% in (1) to 42.8% in sodium salt (PUQHAM) [14], providing extra stabilization in addition to the presence of the abovementioned strong hydrogen bonds.…”

“…Besides, alendronic acid crystal structures signed by CSD reference codes GOWZEX [17] and KOJGUL [18] were included into the analysis. So far, there were reports that the title compound exists in dehydrated [14,15] and trihydrate [14] forms.…”