Synthesis and Characterization of Two New Co-Crystals: p-Aminobenzoic Acid with Isonicotinamide and Pyrazine 1:1

Year 2019, , 63 - 68, 28.03.2019

Fureya Elif Ozbek

https://doi.org/10.17350/HJSE19030000122

Abstract

Two co-crystals of p-aminobenzoic acid with isonicotinamide and pyrazine were prepared in acetone-ethanol solution by solvent evaporation method in the 1:1 cytochiometric ratio. Their structures were characterized by FT-IR, 1H NMR and 13C NMR spectroscopies, powder X-Ray diffraction and differential scanning calorimetry DSC method. Both of the structures have shown the COOH/N heterosynthon. The thermal stability of the co-crystals was investigated by using DSC and it was determinated that the melting points of the cocrystals 1 and 2 were lower and in-between from those of their coformers, respectively

Keywords

P-aminobenzoic acid, Isonicotinamide, Pyrazine, Co-crystal

References

• McNamara DP, Childs SL, Giordano J, Iarriccio A, Cassidy J, Shet MS, et al. Use of a Glutaric Acid Cocrystal to Improve Oral Bioavailability of a Low Solubility API. Pharm Res 23(8) (2006) 1888–1897.
• Yadav A, Shete A, Dabke A, Kulkarni P, Sakhare S. Co- crystals: A novel approach to modify physicochemical properties of active pharmaceutical ingredients. Indian J Pharm Sci 71(4) (2009) 359-370.
• Li Z, Huang J, Meng A, Zheng B. Crystal structure, energy band and optical properties of benzoic acid —2-amino-4,6- dimethylpyrimidine (1:1) co-crystals. J Struct Chem 51(1) (2010) 53–59.
• Tiekink ERT, Vittal JJ, Zaworotko M (eds.). Organic crystal engineering: frontiers in crystal engineering. Wiley: Chichester, U.K, 2010.
• Vijayalakshmi A, Vidyavathy B, Vinitha G. Crystal structure, growth and nonlinear optical studies of isonicotinamide p-nitrophenol: A new organic crystal for optical limiting applications. J Cryst Growth 448 (2016) 82–88.
• Sudhakar P, Srivijaya R, Sreekanth BR, Jayanthi PK, Vishweshwar P, Babu MJ, et al. Carboxylic acid–pyridine supramolecular heterocatemer in a co-crystal. J Mol Struct 885(1–3) (2008) 45–49.
• Vishweshwar P, Nangia A, Lynch VM. Recurrence of Carboxylic Acid−Pyridine Supramolecular Synthon in the Crystal Structures of Some Pyrazinecarboxylic Acids. J Org Chem 67(2) (2002) 556–565.
• Akberova SI. New Biological Properties of p-Aminobenzoic Acid. Biol Bull Russ Acad Sci 29(4) (2002) 390–393.
• Batool SS, Gilani SR, Tahir MN, Rüffer T. Synthesis, and structural characterization of mixed ligand copper(II) complexes of N,N,N',N’-tetramethylethylenediamine incorporating carboxylates. J Mol Struct 1148 (2017) 7–14.
• Vijayalakshmi A., Vidyavathy B, Vinitha G. Structure and characterization of a new organic crystal for optical limiting applications, isonicotinamide bis-p-aminobenzoic acid. Ukr J Phys Opt 17(3) (2016) 98–104.
• Arıcı M, Yeşilel OZ, Acar E, Dege N. Synthesis, characterization and properties of nicotinamide and isonicotinamide complexes with diverse dicarboxylic acids. Polyhedron 127 (2017) 293–301.
• Ratajczak HM, Bryndal I, Ledoux-Rak I, Barnes AJ. Search for molecular crystals with NLO properties: 3-Nitrophenol with nicotinamide and isonicotinamide. J Mol Struct 1047 (2013) 310–316.
• Bhardwaj RM, Yang H, Florence AJ. Crystal structure of the co-crystal butylparaben–isonicotinamide (1/1). Acta Crystallogr Sect E Crystallogr Commun 72(1) (2016) 53–55.
• Gotoh K, Ishida H. 4-Chloro-2-nitrobenzoic acid–pyrazine (2/1). Acta Crystallogr Sect E Struct Rep Online 67(12) (2011) o3222–o3222.
• Wen G-J, Gu L-S, Sun B-W. Tuning crystal structure and absorption properties of 4-hydroxyisophthalic acid co- crystals using pyrazine derivatives. J Mol Struct 1150 (2017) 96–102.
• Amombo Noa FM, Mehlana G. Co-crystals and salts of vanillic acid and vanillin with amines. CrystEngComm 20(7) (2018) 896–905.
• Steed JW. The role of co-crystals in pharmaceutical design. Trends Pharmacol Sci 34(3) (2013) 185–193.
• Gadade DD, Pekamwar SS, Lahoti SR, Patni SD, Sarode MC. Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release. Marmara Pharm J 21(24530) (2016) 78–88.
• Jones W, Motherwell WDS, Trask AV. Pharmaceutical Cocrystals: An Emerging Approach to Physical Property Enhancement. MRS Bull 31(11) 2006 875–879.
• Pavia DL, Lampman GM, Kriz GS. Introduction to spectroscopy: a guide for students of organic chemistry. 3. ed. Brooks/Cole: South Melbourne, 2001.
• Manin AN, Voronin AP, Drozd KV, Manin NG, Bauer-Brandl A, Perlovich GL. Cocrystal screening of hydroxybenzamides with benzoic acid derivatives: A comparative study of thermal and solution-based methods. Eur J Pharm Sci 65 (2014) 56–64.
• Lu E, Rodríguez-Hornedo N, Suryanarayanan R. A rapid thermal method for cocrystal screening. CrystEngComm 10(6) (2008) 665–668.