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).
Published in | Science Journal of Chemistry (Volume 7, Issue 6) |
DOI | 10.11648/j.sjc.2019070612 |
Page(s) | 110-113 |
Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
Copyright |
Copyright © The Author(s), 2020. Published by Science Publishing Group |
Crystal Structure, Diisopropylammonium, Maleate, Hydrogen Bonds, Sheet
[1] | 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. |
[2] | 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. |
[3] | 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. |
[4] | J. R. Guido and K. M. Michaela, “Bis(diisopropylammonium) sulfate,” Acta Cryst, vol. E60, pp. o985–o98, May 2004. |
[5] | G. T. Gyula, M. V. Nóra, and B. Petra, “Crystal structure of levomepromazine maleate,” Acta Cryst. Vol. E72, pp. 612–615, May, 2016. |
[6] | 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. |
[7] | 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. |
[8] | 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. |
[9] | 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. |
[10] | 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. |
[11] | Bruker (2016). Apex3 v2016.9-0, Saint V8.34A, SAINT V8.37A, Bruker AXS Inc.: Madison (WI), USA, 2013/2014. |
[12] | G. M. Sheldrick (2015). (SHELXL2014/7). Acta Cryst. C71, 3-8. |
[13] | Nakamoto K. (1997). Infrared and Raman Spectra of Inorganic and Coordination Compounds, Edited by John Wiley and Sons, 5th Edition |
[14] | D. Seye, L. Diop, C. A. K. Diop and D. Geiger, “Diisopropylammonium hydrogen phthalate,” Acta Cryst, IUCrData 3, x180704, May 2018. |
[15] | D. Seye, C. A. K. Diop L. Diop, and D. Geiger, “Diisopropylammonium benzenesulfonate,” Acta Cryst. IUCrData 3, x180876, June 2018. |
[16] | 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. |
[17] | 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. |
[18] | 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. |
[19] | 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. |
APA Style
Dame Seye, Assane Toure, Momath Lo, Cheikh Abdoul Khadir Diop, Libasse Diop, et al. (2020). Crystal Structure of Diisopropylammonium Hydrogen Maleate. Science Journal of Chemistry, 7(6), 110-113. https://doi.org/10.11648/j.sjc.2019070612
ACS Style
Dame Seye; Assane Toure; Momath Lo; Cheikh Abdoul Khadir Diop; Libasse Diop, et al. Crystal Structure of Diisopropylammonium Hydrogen Maleate. Sci. J. Chem. 2020, 7(6), 110-113. doi: 10.11648/j.sjc.2019070612
AMA Style
Dame Seye, Assane Toure, Momath Lo, Cheikh Abdoul Khadir Diop, Libasse Diop, et al. Crystal Structure of Diisopropylammonium Hydrogen Maleate. Sci J Chem. 2020;7(6):110-113. doi: 10.11648/j.sjc.2019070612
@article{10.11648/j.sjc.2019070612, author = {Dame Seye and Assane Toure and Momath Lo and Cheikh Abdoul Khadir Diop and Libasse Diop and David Geiger}, title = {Crystal Structure of Diisopropylammonium Hydrogen Maleate}, journal = {Science Journal of Chemistry}, volume = {7}, number = {6}, pages = {110-113}, doi = {10.11648/j.sjc.2019070612}, url = {https://doi.org/10.11648/j.sjc.2019070612}, eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.2019070612}, abstract = {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).}, year = {2020} }
TY - JOUR T1 - Crystal Structure of Diisopropylammonium Hydrogen Maleate AU - Dame Seye AU - Assane Toure AU - Momath Lo AU - Cheikh Abdoul Khadir Diop AU - Libasse Diop AU - David Geiger Y1 - 2020/02/11 PY - 2020 N1 - https://doi.org/10.11648/j.sjc.2019070612 DO - 10.11648/j.sjc.2019070612 T2 - Science Journal of Chemistry JF - Science Journal of Chemistry JO - Science Journal of Chemistry SP - 110 EP - 113 PB - Science Publishing Group SN - 2330-099X UR - https://doi.org/10.11648/j.sjc.2019070612 AB - 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). VL - 7 IS - 6 ER -