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

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 co-crystals 1 and 2 were lower and in-between from those of their coformers, respectively.

Keywords:

Waste tire; P-aminobenzoic acid; Isonicotinamide; Pyrazine; Co-crystal.

DOI: 10.17350/HJSE19030000122

Full Text: page_white_acrobat.png

Downloads

Download data is not yet available.

References

1. Korotkova EI, Kratochvíl B. Pharmaceutical Cocrystals. Procedia Chem 10 (2014) 473–476.

2. Gadade DD, Pekamwar SS. Pharmaceutical Cocrystals: Regulatory and Strategic Aspects, Design and Development. Adv Pharm Bull 6(4) (2016) 479–494.

3. Bond AD. What is a co-crystal? CrystEngComm 9(9) (2007) 833-834.

4. Stoler E, Warner J. Non-Covalent Derivatives: Cocrystals and Eutectics. Molecules 20(8) (2015) 14833–14848.

5. Cannon AS, Warner JC. Noncovalent Derivatization: Green Chemistry Applications of Crystal Engineering. Cryst Growth Des 2(4) 2002 255–257.

6. Hickey MB, Peterson ML, Scoppettuolo LA, Morrisette SL, Vetter A, Guzmán H, et al. Performance comparison of a co-crystal of carbamazepine with marketed product. Eur J Pharm Biopharm 67(1) (2007) 112–119.

7. Amombo Noa FM, Jacobs A. Phenylacetic acid co-crystals with acridine, caffeine, isonicotinamide and nicotinamide: Crystal structures, thermal analysis, FTIR spectroscopy and Hirshfeld surface analysis. J Mol Struct 1139 (2017) 60–66.

8. Boyd S, Back K, Chadwick K, Davey RJ, Seaton CC. Solubility Metastable Zone Width Measurement and Crystal Growth of the 1:1 Benzoic Acid/Isonicotinamide Cocrystal in Solutions of Variable Stoichiometry. J Pharm Sci 99(9) (2010) 3779–3786.

9. Patil SP, Modi SR, Bansal AK. Generation of 1:1 Carbamazepine:Nicotinamide cocrystals by spray drying. Eur J Pharm Sci 62 (2014) 251–257.

10. 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.

11. 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.

12. 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.

13. Tiekink ERT, Vittal JJ, Zaworotko M (eds.). Organic crystal engineering: frontiers in crystal engineering. Wiley: Chichester, U.K, 2010.

14. 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.

15. 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.

16. 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.

17. Akberova SI. New Biological Properties of p-Aminobenzoic Acid. Biol Bull Russ Acad Sci 29(4) (2002) 390–393.

18. 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.

19. 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.

20. 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.

21. 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.

22. 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.

23. Gotoh K, Ishida H. 4-Chloro-2-nitrobenzoic acid–pyrazine (2/1). Acta Crystallogr Sect E Struct Rep Online 67(12) (2011) o3222–o3222.

24. 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.

25. Amombo Noa FM, Mehlana G. Co-crystals and salts of vanillic acid and vanillin with amines. CrystEngComm 20(7) (2018) 896–905.

26. Steed JW. The role of co-crystals in pharmaceutical design. Trends Pharmacol Sci 34(3) (2013) 185–193.

27. 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.

28. Jones W, Motherwell WDS, Trask AV. Pharmaceutical Cocrystals: An Emerging Approach to Physical Property Enhancement. MRS Bull 31(11) 2006 875–879.

29. Pavia DL, Lampman GM, Kriz GS. Introduction to spectroscopy: a guide for students of organic chemistry. 3. ed. Brooks/Cole: South Melbourne, 2001.

30. 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.

31. Lu E, Rodríguez-Hornedo N, Suryanarayanan R. A rapid thermal method for cocrystal screening. CrystEngComm 10(6) (2008) 665–668.
Published
2019-03-28
How to Cite
Ozbek, F. E. (2019). Synthesis and Characterization of Two New Co-Crystals: p-Aminobenzoic Acid with Isonicotinamide and Pyrazine (1:1). Hittite Journal of Science & Engineering, 6(1), 63-68. Retrieved from https://www.hjse.hitit.edu.tr/hjse/index.php/HJSE/article/view/HJSE19030000122
Section
SCIENCE