Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties. (21st September 2017)

• Record Type: Journal Article
• Authors: Golovnev, Nicolay N.; Molokeev, Maxim S.; Lesnikov, Maxim K.; Atuchin, Victor V.
• Is Part Of: Journal of physical organic chemistry. Volume 31:Number 3(2018)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2017-09-21
• Subjects: barbituric and thiobarbituric acids -- ciprofloxacin -- infrared spectroscopy -- salt cocrystal -- thermal stability -- X‐ray diffraction; Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.3773
• Languages: English
• ISSNs: 0894-3230

Abstract

Abstract: Ciprofloxacin (CfH, C17 H18 FN3 O3 ) crystallizes with 2‐thiobarbituric (H2 tba) and barbituric acid (H2 ba) in the aqueous solution to yield salt CfH2 (Htba)·3H2 O (1 ), salt cocrystal CfH2 (Hba)(H2 ba)·3H2 O (2 ), and salt CfH2 (Hba)·H2 O (3 ). The compounds are structurally characterized by the X‐ray single‐crystal diffraction. The numerous intermolecular hydrogen bonds N–H⋯O and O–H⋯O formed by water molecules, Htba − /Hba − and CfH2 + ions, and H2 ba molecules stabilize the crystal structures of1 to3 . Hydrogen bonds form a 2D plane network in the salts of1 and3 and a 3D network in the salt cocrystal of2 . There are different π‐π interactions in1 to3 . The compounds have been characterized by powder X‐ray diffraction, thermogravimetry/differential scanning calorimetry, and Fourier transform infrared spectroscopy. The compounds dehydration ends at 130°C to 150°C, and their oxidative decomposition is observed in the range of 250°C to 275°C. Abstract : Ciprofloxacin (C17 H18 FN3 O3 ) crystallizes with 2‐thiobarbituric and barbituric acid in the aqueous solution to yield salt CfH2 (Htba)·3H2 O (1 ), salt cocrystal CfH2 (Hba)(H2 ba)·3H2 O (2 ), and salt CfH2 (Hba)·H2 O (3 ). The numerous intermolecular hydrogen bonds N–H⋯O and O–H⋯O formed by water molecules, Htba − /Hba − and CfH2 + ions, and H2 ba molecules stabilize the crystal structures of1 to3 . Hydrogen bonds form a 2D plane network in the salts of1 and3 and a 3D network in the salt cocrystal of2 .