Novel Perchlorate and Sulphate Salts of 2-Aminonicotinic Acid: Synthesis, Characterization, Thermal Studies and Hirshfeld Surface Analysis

Citation: MA Yu-Heng, GE Shu-Wang, SHEN Ya, SUN Bai-Wang. Novel Perchlorate and Sulphate Salts of 2-Aminonicotinic Acid: Synthesis, Characterization, Thermal Studies and Hirshfeld Surface Analysis[J]. Chinese Journal of Structural Chemistry, 2016, 35(1): 7-15. doi: 10.14102/j.cnki.0254-5861.2011-0684 shu

Novel Perchlorate and Sulphate Salts of 2-Aminonicotinic Acid: Synthesis, Characterization, Thermal Studies and Hirshfeld Surface Analysis

1.
a School of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, China;
b Jiangsu Chia Tai Qingjiang Pharmaceutical Co.
b Jiangsu Chia Tai Qingjiang Pharmaceutical Co., Ltd.;
3.
c Department of Chemical and Pharmaceutical Engineering of Southeast University Chengxian College, Nanjing 210088, China;
4.
d High School Affiliated to Nanjing Normal University, Xincheng Junior School Yikangjie Campus, 210019, China

通讯作者: SUN Bai-Wang,

基金项目:
This work was supported by the prospective joint research project of Jiangsu province (BY20122193) (BY20122193)

the Fundamental Research Funds for the Central Universities (CXZZ12_0119) (CXZZ12_0119)

摘要: Since 2-aminonicotinic acid is a zwitterionic molecule, the salt or co-crystal strategy was used for the precipitation under identical conditions and obtained two novel salts: salt 1 with 2:1:2 stoichiometry of 2-aminonicotinic acid:perchloric acid: H₂O and salt 2 with 2:1:3 stoichiometry of 2-aminonicotinic acid: sulfuric acid: H₂O. Their crystal structures were characterized by single-crystal X-ray diffraction, differential scanning calorimetry (DSC) and thermogravimetric analyses (TGA). The structure determination shows that two salts are both primarily stabilized by the strong N-H…O hydrogen bonding interaction between 2-aminonicotinic acid and its corresponding acids. Constituents of the salt-crystalline phase were also investigated in terms of Hirshfeld surfaces. In the crystal lattice, a three-dimensional hydrogen-bonded network is observed, including the formation of a two-dimensional molecular scaffolding motif. Hirshfeld surfaces and fingerprint plots of two salts show that the structures are stabilized by H…H, O-H…O and C-O…π intermolecular interactions.

关键词:

English

Novel Perchlorate and Sulphate Salts of 2-Aminonicotinic Acid: Synthesis, Characterization, Thermal Studies and Hirshfeld Surface Analysis

1.
a School of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, China;
b Jiangsu Chia Tai Qingjiang Pharmaceutical Co.
b Jiangsu Chia Tai Qingjiang Pharmaceutical Co., Ltd.;
3.
c Department of Chemical and Pharmaceutical Engineering of Southeast University Chengxian College, Nanjing 210088, China;
4.
d High School Affiliated to Nanjing Normal University, Xincheng Junior School Yikangjie Campus, 210019, China

Corresponding author: SUN Bai-Wang,

Received Date: 12 February 2015
Fund Project:

Abstract: Since 2-aminonicotinic acid is a zwitterionic molecule, the salt or co-crystal strategy was used for the precipitation under identical conditions and obtained two novel salts: salt 1 with 2:1:2 stoichiometry of 2-aminonicotinic acid:perchloric acid: H₂O and salt 2 with 2:1:3 stoichiometry of 2-aminonicotinic acid: sulfuric acid: H₂O. Their crystal structures were characterized by single-crystal X-ray diffraction, differential scanning calorimetry (DSC) and thermogravimetric analyses (TGA). The structure determination shows that two salts are both primarily stabilized by the strong N-H…O hydrogen bonding interaction between 2-aminonicotinic acid and its corresponding acids. Constituents of the salt-crystalline phase were also investigated in terms of Hirshfeld surfaces. In the crystal lattice, a three-dimensional hydrogen-bonded network is observed, including the formation of a two-dimensional molecular scaffolding motif. Hirshfeld surfaces and fingerprint plots of two salts show that the structures are stabilized by H…H, O-H…O and C-O…π intermolecular interactions.

Key words:

1. [1]
  (1) Meyer, M. D.; Altenbach, R. J.; Bai, H.; Basha, F. Z.; Carroll, W. A.; Kerwin, J. F.; Lebold, S. A.; Lee, E.; Pratt, J. K.; Sippy, K. B.; Tietje, K.; Wendt, M. D.; Brune, M. E.; Buckner, S. A.; Hancock, A. A.; Drizin, I. Structure-activity studies for a novel series of bicyclic substituted hexahydrobenz[e]isoindole α1A adrenoceptor antagonists as potential agents for the symptomatic treatment of benign prostatic hyperplasia. J. Med. Chem. 2001, 44, 1971-1985.(1) Meyer, M. D.; Altenbach, R. J.; Bai, H.; Basha, F. Z.; Carroll, W. A.; Kerwin, J. F.; Lebold, S. A.; Lee, E.; Pratt, J. K.; Sippy, K. B.; Tietje, K.; Wendt, M. D.; Brune, M. E.; Buckner, S. A.; Hancock, A. A.; Drizin, I. Structure-activity studies for a novel series of bicyclic substituted hexahydrobenz[e]isoindole α1A adrenoceptor antagonists as potential agents for the symptomatic treatment of benign prostatic hyperplasia. J. Med. Chem. 2001, 44, 1971-1985.
2. [2]
  (2) Congiu, C.; Cocco, M. T.; Lilliu, V.; Onnis, V. New potential anticancer agents based on the anthranilic acid scaffold. Synthesis and evaluation of biological activity. J. Med. Chem. 2005, 48, 8245-8252.(2) Congiu, C.; Cocco, M. T.; Lilliu, V.; Onnis, V. New potential anticancer agents based on the anthranilic acid scaffold. Synthesis and evaluation of biological activity. J. Med. Chem. 2005, 48, 8245-8252.
3. [3]
  (3) Charles, D. H.; Victor, G. B. Hydroxamic acids and N-hydroxyimides related to pyridine, pyrazine, and quinoxaline. J. Org. Chem. 1970, 35, 1471-1475.(3) Charles, D. H.; Victor, G. B. Hydroxamic acids and N-hydroxyimides related to pyridine, pyrazine, and quinoxaline. J. Org. Chem. 1970, 35, 1471-1475.
4. [4]
  (4) Becker, D. P.; Flynn, D. L.; Moormann, A. E.; Nosal, R.; Villamil, C. I.; Loeffler, R.; Gullikson, G. W.; Moummi, C.; Yang, D. C. Pyrrolizidine esters and amides as 5-HT4 receptor agonists and antagonists. J. Med. Chem. 2006, 49, 1125-1139.(4) Becker, D. P.; Flynn, D. L.; Moormann, A. E.; Nosal, R.; Villamil, C. I.; Loeffler, R.; Gullikson, G. W.; Moummi, C.; Yang, D. C. Pyrrolizidine esters and amides as 5-HT4 receptor agonists and antagonists. J. Med. Chem. 2006, 49, 1125-1139.
5. [5]
  (5) Zografos, A. L.; Mitsos, C. A.; Markopoulou, O. L. Chemoselective cyclization of aminonicotinic acid derivatives to 1,8-naphthyridin-2-ones via a potential intramolecular azadiene-Ketene electrocyclization reaction. J. Org. Chem. 2001, 66, 4413-4415(5) Zografos, A. L.; Mitsos, C. A.; Markopoulou, O. L. Chemoselective cyclization of aminonicotinic acid derivatives to 1,8-naphthyridin-2-ones via a potential intramolecular azadiene-Ketene electrocyclization reaction. J. Org. Chem. 2001, 66, 4413-4415
6. [6]
  (6) Huang, H. H.; Wilkes, G. L.; Orler, B. Ceramers-hybrid materials incorporating polymeric oligomeric species into inorganic glasses utilizing a sol-gel approac. Polym. Prepr. 1985, 14, 557-564.(6) Huang, H. H.; Wilkes, G. L.; Orler, B. Ceramers-hybrid materials incorporating polymeric oligomeric species into inorganic glasses utilizing a sol-gel approac. Polym. Prepr. 1985, 14, 557-564.
7. [7]
  (7) Desiraju, G. R. Crystal engineering: a holistic view. Angew. Chem. 1995, 107, 2541-2558.(7) Desiraju, G. R. Crystal engineering: a holistic view. Angew. Chem. 1995, 107, 2541-2558.
8. [8]
  (8) Berrah, F.; Bouacida, S.; Anana, H.; Roisnel, T. 2-Amino-3-carboxypyridinium perchlorate. Acta Crystallogr. E 2012, E68, o1601-1602.(8) Berrah, F.; Bouacida, S.; Anana, H.; Roisnel, T. 2-Amino-3-carboxypyridinium perchlorate. Acta Crystallogr. E 2012, E68, o1601-1602.
9. [9]
  (9) Berrah, F.; Ouakkaf, A.; Bouacida, S.; Roisnel, T. Bis(2-amino-3-carboxypyridinium) sulfatetrihydrate. Acta Crystallogr. E 2011, E67, o953-o954.(9) Berrah, F.; Ouakkaf, A.; Bouacida, S.; Roisnel, T. Bis(2-amino-3-carboxypyridinium) sulfatetrihydrate. Acta Crystallogr. E 2011, E67, o953-o954.
10. [10]
  (10) Berrah, F.; Roisnel, T.; Bouacida, S. 2-Amino-3-carboxypyridinium nitrat. Acta Crystallogr. E 2011, E67, o2057-2058.(10) Berrah, F.; Roisnel, T.; Bouacida, S. 2-Amino-3-carboxypyridinium nitrat. Acta Crystallogr. E 2011, E67, o2057-2058.
11. [11]
  (11) Bouchene, R.; Bouacida, S.; Berrah, F.; Daran, J. C. 2-Amino-3-carboxypyridinium chloride hemihydrate. Acta Crystallogr. E 2012, E68, o1493-1494.(11) Bouchene, R.; Bouacida, S.; Berrah, F.; Daran, J. C. 2-Amino-3-carboxypyridinium chloride hemihydrate. Acta Crystallogr. E 2012, E68, o1493-1494.
12. [12]
  (12) Aaltonen, J.; Alleso, M.; Mirza, S.; Koradia, K.; Gordon, K. C.; Rantanen, J. Solid form screening - a review. Eur. J. Pharm. Biopharm. 2009, 71, 23-27.(12) Aaltonen, J.; Alleso, M.; Mirza, S.; Koradia, K.; Gordon, K. C.; Rantanen, J. Solid form screening - a review. Eur. J. Pharm. Biopharm. 2009, 71, 23-27.
13. [13]
  (13) Thallapally, P. K.; Jetti, R. K. R.; Katz, A. K.; Carrell, H. L.; Singh, K.; Lahiri, K.; Kotha, S.; Boese, R.; Desiraju, G. R. Polymorphism of 1,3,5-trinitrobenzene induced by a trisindane additive. Angew. Chem. Int. Ed. 2004, 43, 1149-1155.(13) Thallapally, P. K.; Jetti, R. K. R.; Katz, A. K.; Carrell, H. L.; Singh, K.; Lahiri, K.; Kotha, S.; Boese, R.; Desiraju, G. R. Polymorphism of 1,3,5-trinitrobenzene induced by a trisindane additive. Angew. Chem. Int. Ed. 2004, 43, 1149-1155.
14. [14]
  (14) Threlfall, T. L. Analysis of organic polymorphs: a review. Analyst. 1995, 120, 2435-2460.(14) Threlfall, T. L. Analysis of organic polymorphs: a review. Analyst. 1995, 120, 2435-2460.
15. [15]
  (15) Hua, G. Y.; Ge, G. Hydrothermal synthesis and crystal structure of two polymorphs of (3-nitro-4-bromophenyl)acetic acid. Journal of Chemical Research 2011, 11, 644-646.(15) Hua, G. Y.; Ge, G. Hydrothermal synthesis and crystal structure of two polymorphs of (3-nitro-4-bromophenyl)acetic acid. Journal of Chemical Research 2011, 11, 644-646.
16. [16]
  (16) Rigaku CrystalClear, Version 14.0. Rigaku Corporation. Tokyo, Japan 2005.(16) Rigaku CrystalClear, Version 14.0. Rigaku Corporation. Tokyo, Japan 2005.
17. [17]
  (17) Sheldrick, G. M. SHElXS97: Programs for Crystal Structure Analysis. University of Göttingen, Germany 1997.(17) Sheldrick, G. M. SHElXS97: Programs for Crystal Structure Analysis. University of Göttingen, Germany 1997.
18. [18]
  (18) Brandenburg, K. DIAMOND: Crystal and Molecular Structure Visualization, Version 3.1b, Crystal Impact GbR,Bonn, Germany 2006(18) Brandenburg, K. DIAMOND: Crystal and Molecular Structure Visualization, Version 3.1b, Crystal Impact GbR,Bonn, Germany 2006
19. [19]
  (19) Mercury 2.3 Supplied with Cambridge Structural Database, CCDC, Cambridge, U.K. 2003-2004.(19) Mercury 2.3 Supplied with Cambridge Structural Database, CCDC, Cambridge, U.K. 2003-2004.
20. [20]
  (20) Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J. CrystalExplorer 3.0. University of Western Australia, Perth, Australia 2012.(20) Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J. CrystalExplorer 3.0. University of Western Australia, Perth, Australia 2012.
21. [21]
  (21) Blatov, V. A.; Shevchenko, A. P.; Serenzhkin, V. N. Crystal space analysis by means of Voronoi-Dirichlet polyhedral. Acta Cryst. 1995, A51, 909-916.(21) Blatov, V. A.; Shevchenko, A. P.; Serenzhkin, V. N. Crystal space analysis by means of Voronoi-Dirichlet polyhedral. Acta Cryst. 1995, A51, 909-916.
22. [22]
  (22) Spackman, M. A.; Javatilaka, D. Hirshfeld surface analysis. CrystEngComm. 2009, 11, 19-32.(22) Spackman, M. A.; Javatilaka, D. Hirshfeld surface analysis. CrystEngComm. 2009, 11, 19-32.
23. [23]
  (23) Ma, Y. H.; Ge, S. W.; Sun, B. W. Synthesis, characterization and theoretical studies of a novel salt (dexmedetomidine: perchloric acid = 1:1) and the investigation of its stability. Chin. J. Struct. Chem. 2015, 34, 1179-1186.(23) Ma, Y. H.; Ge, S. W.; Sun, B. W. Synthesis, characterization and theoretical studies of a novel salt (dexmedetomidine: perchloric acid = 1:1) and the investigation of its stability. Chin. J. Struct. Chem. 2015, 34, 1179-1186.
24. [24]
  (24) Feng, C.; Gao, G. Y.; Qu, Z. R.; Sun, L. N.; Zhao, H. Exploration of supramolecular architecture in complexes with 1-substituted-1H-[1,2,3]-triazole-4-carboxylic acid: structural elucidation and Hirshfeld surface analysis. J. Inorg. Organomet. P 2015, 25, 1233-1238.(24) Feng, C.; Gao, G. Y.; Qu, Z. R.; Sun, L. N.; Zhao, H. Exploration of supramolecular architecture in complexes with 1-substituted-1H-[1,2,3]-triazole-4-carboxylic acid: structural elucidation and Hirshfeld surface analysis. J. Inorg. Organomet. P 2015, 25, 1233-1238.

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沈阳化工大学材料科学与工程学院沈阳 110142

Novel Perchlorate and Sulphate Salts of 2-Aminonicotinic Acid: Synthesis, Characterization, Thermal Studies and Hirshfeld Surface Analysis

通讯作者: SUN Bai-Wang,

English

Novel Perchlorate and Sulphate Salts of 2-Aminonicotinic Acid: Synthesis, Characterization, Thermal Studies and Hirshfeld Surface Analysis

Corresponding author: SUN Bai-Wang,

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Novel Perchlorate and Sulphate Salts of 2-Aminonicotinic Acid: Synthesis, Characterization, Thermal Studies and Hirshfeld Surface Analysis

通讯作者: SUN Bai-Wang,

English

Novel Perchlorate and Sulphate Salts of 2-Aminonicotinic Acid: Synthesis, Characterization, Thermal Studies and Hirshfeld Surface Analysis

Corresponding author: SUN Bai-Wang,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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