Science Journal of Chemistry
Volume 7, Issue 6, December 2019, Pages: 110-113
Received: Jan. 7, 2020;
Accepted: Jan. 29, 2020;
Published: Feb. 11, 2020
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Dame Seye, Mineral and Analytical Chemistry Laboratory, Department of Chemistry, Faculty of Science and Technology, Cheikh Anta Diop University, Dakar, Senegal
Assane Toure, Mineral and Analytical Chemistry Laboratory, Department of Chemistry, Faculty of Science and Technology, Cheikh Anta Diop University, Dakar, Senegal
Momath Lo, Laboraory of Organic Physical Chemistry Instrumental Analysis, Department of Chemistry, Faculty of Science and Technology, Cheikh Anta Diop University, Dakar, Senegal
Cheikh Abdoul Khadir Diop, Mineral and Analytical Chemistry Laboratory, Department of Chemistry, Faculty of Science and Technology, Cheikh Anta Diop University, Dakar, Senegal
Libasse Diop, Mineral and Analytical Chemistry Laboratory, Department of Chemistry, Faculty of Science and Technology, Cheikh Anta Diop University, Dakar, Senegal
David Geiger, Department of Chemistry, Geneseo Faculty, State University of New York, Geneseo, New York, USA
Use of salts and co-crystals of active pharmaceutical ingredients (APIs) as a method for tuning their delivery and activity is an area of growing interest. Modifying API properties such as solubility by finding new salts that employ similar hydrogen-bonding have been successful. In an effort to further study the hydrogen-bonding patterns of the maleate ion with other diisopropylammonium we report here the synthesis and diisopropylammonium maleate. The salt was isolated from reaction between diisopropylamine and maleic acid in methanol. The results of elementary analyzes (CHN) showed the presence of the nitrogen atom of diisopropylamine, carbon atoms and hydrogen. The IR spectrum of diisopropylammonium hydrogen maleate, showed the presence of two intense bands due to the vibrations of symmetricand anti-symmetric valence of the carboxylate group and a wide absorption due to the NH2 groups of the cation. Those which has been confirmed by crystallography. The asymmetric unit contains one diisopropylammonium cation, iPr2NH2+ and one hydrogen maleate anion. In the structure, anions which present an inner O-H…O hydrogen bond are linked to cations through N-H…O hydrogen bonds leading to infinite chains. Chains are connected to their neighbours through weak C-H…O hydrogen bonds affording a layer. The study of the interactions of diisopropylammonium hydrogen menaleate, by the presence of hydrogen bonds leading to supramolecular architectures has shown the possibility of its use in Active Pharmaceutical Ingrédients (API).
Cheikh Abdoul Khadir Diop,
Crystal Structure of Diisopropylammonium Hydrogen Maleate, Science Journal of Chemistry.
Vol. 7, No. 6,
2019, pp. 110-113.
V. P. Cerreia, R. Chierotti, M and R. Gobetto, “Pharmaceutical aspects of salt and cocrystal forms of APIs and characterization challenges,” Advanced. Drug. Deliver, vol. 117, pp. 86–110, August 2017.
M. Maha, E. J. Daron, R. Mohamed and S. S. Wajda, “Crystal structure of 2,5-dimethylanilinium hydrogen maleate,” Acta Cryst, vol. E70, pp. 1183–1184. October 2014.
W. Intissar, V. Arto, R. Mohamed and S. S Wajda, “Crystal structure of 2-methyl¬piperazine-1,4-diium bis(hydrogen maleate),”Acta Cryst, vol. E71, pp. 193–194, March 2015.
J. R. Guido and K. M. Michaela, “Bis(diisopropylammonium) sulfate,” Acta Cryst, vol. E60, pp. o985–o98, May 2004.
G. T. Gyula, M. V. Nóra, and B. Petra, “Crystal structure of levomepromazine maleate,” Acta Cryst. Vol. E72, pp. 612–615, May, 2016.
P. K. Steven, N. Asako, H. D. John, G. D. Keith, R. W. Matthew and R. D. Robin, “Understanding the Effects of Ionicity in Salts, Solvates, Co-Crystals, Ionic Co-Crystals, and Ionic Liquids, Rather than Nomenclature, Is Critical to Understanding Their Behavior,” Cryst. Growth Des, vol. 13, pp. 965–975 February, 2013.
M. H. Rania, A. G. Heba, A. H. M. Salma, K. Noha, A. Toka, A, Alaa, Y, Nesreen, N. Sandy, M and A. Abdel kader. “Gelatinized core liposomes: A new Trojan horse for the development of a novel timolol maleate glaucoma medication,” International Journal of Pharm, vol. 5 56, pp. 192-199, February, 2019.
B. P, Nagori, A, Maru, M. Pankaj and G. Subhash, “Method Development and Its Validation for Simultaneous Estimation of Timolol Maleate and Dorzolamide Hydrochloride in as API and in Ophthalmic Solution Dosage Form by RPHPLC,” J. Chem. Pharm. Res, vol. 3, No. 4, 866-874, 2011.
B. Rehana, S. N. Baqir, S. H. Mouhammad and R. Najia,“design and evaluation of a new formulation of enalapril maleate tablet,” Pak. J. Pharm. Sci, vol. 24, No. 2, pp. 211-215, April, 2011.
C. Yan, X-Y. Wu, O-Y. Luo, L. Su, Y-T. Ding, Y. Jiang, D-C. Yu “Diisopropylamine dichloroacetate alleviates liver fibrosis through inhibiting activation and proliferation of hepatic stellate cells,” Int. J. Clin. Exp. Med. 2019, 12, 3440-3448.
Bruker (2016). Apex3 v2016.9-0, Saint V8.34A, SAINT V8.37A, Bruker AXS Inc.: Madison (WI), USA, 2013/2014.
G. M. Sheldrick (2015). (SHELXL2014/7). Acta Cryst. C71, 3-8.
Nakamoto K. (1997). Infrared and Raman Spectra of Inorganic and Coordination Compounds, Edited by John Wiley and Sons, 5th Edition
D. Seye, L. Diop, C. A. K. Diop and D. Geiger, “Diisopropylammonium hydrogen phthalate,” Acta Cryst, IUCrData 3, x180704, May 2018.
D. Seye, C. A. K. Diop L. Diop, and D. Geiger, “Diisopropylammonium benzenesulfonate,” Acta Cryst. IUCrData 3, x180876, June 2018.
R. J. Guido and M. K Michaela, “Synthesis and Structural Characterization of Diisopropylammonium Trifluoroacetate and Diisoproplyammonium Pentafluoropropionate,” Z. Naturforsch. B Chem. Sci, vol. 65b, pp. 479-484, 2010.
L. Zhihao, H. Kaikai, J. Shouwen, D. Aihua, W. Yining, D, Lingfeng, G. Xingjun and w. Daqi, “Crystal and molecular structures of sixteen charge-assisted hydrogen bond-mediated diisopropylammonium salts from different carboxylic acids,” J. Mol. Struct, vol. 1146, pp. 577- 591, October 2017.
A. Piecha-Bisiorek,, A. Gagor, D. Isakov,, P. Zielinski, M. Galazka and R. Jakubas, “Phase sequence in diisopropylammonium iodide: avoided ferroelectricity by the appearance of a reconstructed phase,” Inorg. Chem. Front, vol. 4, pp. 553-558, January, 2017.
C. R. Groom, I. J. Bruno, M. P. Lightfoot, and S. C. Ward, “The Cambridge Structural Database,” Acta Cryst, vol. B72, pp. 171–179, March 2016.