3-Hidroksibenzoik Asit – İzonikotinamid (1/1) Ko-Kristalinin Sentezi ve Spektroskopik Karakterizasyonu
Bu çalışmada 3-hidroksibenzoik asit ile izonikotinamidin ko-kristali aseton-etanol çözeltisi içinde 1:1 oranında çözücü buharlaştırma yöntemi ile hazırlandı. Yapıları FT-IR, 1H NMR ve 13C NMR spektroskopileri, toz X ışını diffraksiyonu (XRD) ve diferansiyel tarama kalorimetresi (DSC) yöntemi ile karakterize edildi.
Synthesis and Spectroscopic Characterization of 3-Hydroxybenzoic Acid -Isonicotinamide (1/1) Co-Crystalline
The co-crystal of 3-hydroxybenzoic acid and the isonicotinamide were prepared by solvent evaporation in a 1: 1 ratio in acetoneethanol solution. Structures were characterized by FT-IR, 1H NMR and 13C NMR spectroscopy, Powder X-ray diffraction (XRD) and differential scanning calorimetry (DSC) method.
___
- Akalin, E., Yilmaz, A., Akyuz, S. 2005. Vibrational analysis of isonicotinamide. J. Mol. Struct.,744-747:881-886.
- Arıcı, M., Yeşilel, OZ., Acar, E., Dege, N. 2017. Synthesis, characterization and properties of nicotinamide and isonicotinamide complexes with diverse dicarboxylic acids. Polyhedron., 127: 293–301.
- Ash, M., Ash, I. 2009. Handbook of preservatives. Synapse Information Resources, Endicott, NY .
- Bhardwaj, R.M., Yang, H., Florence, AJ. 2016. Crystal structure of the co-crystal butyl-paraben-isonicotinamide (1/1). Acta. Cryst. E. Crystallogr. Comm., 72: 53–55.
- Bond, AD. 2007. What is a co-crystal? Cryst. Eng. Comm., 9: 833–834.
- Cannon, AS., Warner, JC. 2002. Noncovalent Derivatization:
Green Chemistry Applications of Crystal Engineering. Cryst. Growth. Des., 2: 255–257.
- Childs, SL., Chyall, LJ., Dunlap, JT., Smolenskaya, VN., Stahly, BC., Stahly, GP. 2004. Crystal engineering approach to forming cocrystals of amine hydrochlorides with organic acids. Molecular complexes of fluoxetine hydrochloride with benzoic, succinic, and fumaric acids. J. Am. Chem. Soc., 126: 13335–13342.
- Du, Y., Zhang, H., Xue, J., Fang, H., Zhang, Q., Xia, Y., Li, Y., Hong, Y. 2015. Raman and terahertz spectroscopical investigation of cocrystal formation process of piracetam and 3-hydroxybenzoic acid. Spectrochim Acta. A. Mol. Biomol. Spectrosc., 139: 488–494.
- Li, Z., Huang, J., Meng, A., Zheng, B. 2010. Crystal structure, energy band and optical properties of benzoic acid —2-amino4,6-dimethylpyrimidine (1:1) co-crystals.
- J. Struc. Chem., 51: 53–59. Lou, M., Mao, S-H., Luo, Y-H., Zhao, P., Sun, B-W. 2015. Synthesis, co-crystal structure and characterization of pyrazinamide with m-hydroxybenzoic acid, p-hydroxybenzoic acid and 3,4-dihydroxy benzolic acid. Res. Chem. Intermedıat., 41: 2939–2951.
- Lu, E., Rodríguez-Hornedo, N., Suryanarayanan, R. 2008. A rapid thermal method for cocrystal screening. Cryst. Eng. Comm., 10: 665–668.
- Luo, Y-H., Xu, B., Sun, B-W. 2013. Investigation of supramolecular synthons of p-hydroxybenzoic acid (PHBA): Comparison of its hydrate, co-crystal and salt. J. Cryst. Growth., 374: 88–98.
- Manin, AN., Voronin, AP., Drozd, KV., Manin, NG., BauerBrandl, A., Perlovich, GL. 2014. Cocrystal screening of hydroxybenzamides with benzoic acid derivatives: a comparative study of thermal and solution-based methods. EUFEPS 65: 56–64.
- Maqsood, S., Benjakul, S., Shahidi, F. 2013. Emerging Role of Phenolic Compounds as Natural Food Additives in Fish and Fish Products. Crit. Rev. Food. Sci. Nutr., 53: 162–179.
- Matsumoto, T., Zografi, G. 1999. Physical properties of solid molecular dispersions of indomethacin with poly(vinylpyrrolidone) and poly(vinylpyrrolidone-co-vinylacetate) in relation to indomethacin crystallization. Pharm. Res., 16: 1722–1728.
- McNamara, DP., Childs, SL., Giordano, J., Iarriccio, A., Cassidy, J., Shet, MS., Mannion, R., O’Donnell, E., Park. A. 2006. Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API. Pharm. Res., 23: 1888– 1897.
- Pavia, DL., Lampman, GM., Kriz, GS. 2001. Introduction to Spectroscopy: A Guide for Students of Organic Chemistry. Harcourt College Publishers, 684p.
- Przybyłek, M., Ziółkowska, D., Mroczyńska, K., Cysewski, P. 2016a. Propensity of salicylamide and ethenzamide cocrystallization with aromatic carboxylic acids. EUFEPS. 85: 132–140.
- Przybyłek, M., Ziółkowska, D., Kobierski, M., Mroczyńska, K., Cysewski, P. 2016b. Utilization of oriented crystal growth for screening of aromatic carboxylic acids cocrystallization with urea. J. Cryst. Growth., 433: 128–138.
- Ratajczak, HM., Bryndal, I., Ledoux-Rak, I., Barnes, AJ. 2013. Search for molecular crystals with NLO properties: 3-Nitrophenol with nicotinamide and isonicotinamide. J. Mol. Struct., 1047: 310–316.
- Seefeldt, K., Miller, J., Alvarez-Núñez, F., Rodríguez-Hornedo, N. 2007. Crystallization pathways and kinetics of carbamazepine-nicotinamide cocrystals from the amorphous state by in situ thermomicroscopy, spectroscopy, and calorimetry studies. J. Pharm. Sci., 96: 1147–1158.
- Spectral Database for Organic Compounds SDBS. 1999. https:// sdbs.db.aist.go.jp/sdbs/cgi-bin/landingpage?sdbsno=1390
- Stoler, E., Warner, JC. 2015. Non-Covalent Derivatives: Cocrystals and Eutectics. Molecules 20: 14833–14848.
- Trask, AV., Motherwell, WDS., Jones, W. 2006. Physical stability enhancement of theophylline via cocrystallization. Int. J. Pharm., 320: 114–123.
- Vangala, VR., Chow, PS., Tan, RBH. 2011. Characterization, physicochemical and photo-stability of a co-crystal involving an antibiotic drug, nitrofurantoin, and 4-hydroxybenzoic acid. Cryst.Eng. Comm., 13: 759–762.
- Vishweshwar, P., Nangia, A., Lynch, VM. 2003. Supramolecular synthons in phenol–isonicotinamide adducts. Cryst. Eng. Comm., 5: 164–168.
- Vishweshwar, P., Thaimattam, R., Jaskólski, M., Desiraju, GR. 2002. Supramolecular synthons based on N-H...N and C-H...O hydrogen bonds. Crystal engineering of a helical structure with 5,5-diethylbarbituric acid. Chem. Commun., 7(17): 1830–1831.
- Vishweshwar, P., McMahon, JA., Peterson, ML., Hickey, MB., Shattock, TR., Zaworotko, MJ. 2005. Crystal engineering of pharmaceutical co-crystals from polymorphic active pharmaceutical ingredients. Chem. Comm., 36: 4601-4603.
- Vijayalakshmi A, Vidyavathy B, Vinitha G. 2016. Crystal structure, growth and nonlinear optical studies of isonicotinamide p-nitrophenol: A new organic crystal for optical limiting applications. J. Cryst. Growth., 448: 82–88.
- Wang, L., Zhao, L., Liu, W., Chen, R., Gu, Y., Yang, Y. 2012. Cocrystallization of glycine anhydride with the hydroxybenzoic acids: Controlled formation of dimers via synthons cooperation and structural characterization. Scı. Chına. Chem., 55: 2381– 2387.
- Yadav, AV., Shete, AS., Dabke, AP., Kulkarni, PV., Sakhare, SS. 2009. Co-crystals: a novel approach to modify physicochemical properties of active pharmaceutical ingredients. Indian J. Pharm. Sci., 71: 359–370.