title: Structure determination and characterization of carbendazim hydrochloride dihydrate.
abstract: The objective of this study was to synthesize and characterize the hydrochloride salt of carbendazim with the aim of improving the intrinsic solubility of the parent compound. Carbendazim hydrochloride dihydrate was synthesized for the purpose of increasing the aqueous solubility of the parent drug, carbendazim. This was done with the commonly used saturation and cooling method. The structure was determined by single crystal radiograph crystallography, and the hydrochloride salt was found to be a dihydrate. The salt crystallized in a P 2(1) 2(1) 2(1) (#19) space group, which is typical for nonplanar, achiral, and noncentrosymmetric molecules. The asymmetric unit is comprised of 1 molecule each of carbendazim and chloride and 2 water molecules. The carbendazim molecules arrange themselves in a helical structure, with the waters and the chloride molecules in the channel linking the helix. The crystal lattice is held together by numerous hydrogen bonds, as well as van der Waals interactions. The melting point of the salt is 125.6 degrees C. The solubility of the salt is 6.08 mg/mL, which is a thousand-fold increase from the intrinsic solubility (6.11 microg/mL) of the free base.
authors.affiliation: College of Pharmacy, The University of Arizona, 1703 E Mabel St, Tucson, AZ 85721-0207, USA. machatha@pharmacy.arizona.edu
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Machatha
authors.forename: Tapan
authors.initials: T
authors.lastname: Sanghvi
authors.forename: Samuel H
authors.initials: SH
authors.lastname: Yalkowsky
mesh_terms: D001562:Benzimidazoles / Q000032:analysis / Q000737:chemistry*; D002219:Carbamates / Q000032:analysis / Q000737:chemistry*; D003460:Crystallization; D006851:Hydrochloric Acid / Q000032:analysis / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001562:Benzimidazoles; D002219:Carbamates; C006698:carbendazim; D006851:Hydrochloric Acid