Hydrogen Bonding Assembled 3D Supramolecular Structures Formed by 5-Amino-2,4,6-triiodoisophthalic Acid and N-Heterocyclic Aromatic Ligands

Abstract

Three salts constructed by 5-amino-2,4,6-triiodoisophthalic acid(ATIPA) with N-heterocycles aromatic coformers such as pyridine tetrazolium, tetramethylpyrazine and cyanuric acid were synthesized by slowing evapora-tion of solvent. X-Ray single crystal analysis shows that hydrogen protons of the carboxyl groups transfer to nitrogen atoms of the N-heterocyclic coformers to form N-H … O hydrogen bonds in all the three compounds. A huge amount of H-bonds play significant role in the construction of these compounds and all of them generate 3D structures through strong O-H … N, O-H … O, N-H … O and weak C-H … O hydrogen bonds. Moreover, solvent water molecules are indispensable in the formation of compounds 1 and 3, which constitutes different supramolecular synthons to bridge individual molecules and chains to form stable structures. In addition, these crystal structures were further characterized by thermogravimetric analysis and infrared spectroscopy.

Keywords

Hydrogen bond / Supramolecular structure / X-Ray diffraction / N-Heterocyclic aromatic ligand

References

[1] Ma X, Zhao Y L. Chem. Rev., 2015, 11515: 7794.

[2] Lehn J M. Chem. Soc. Rev., 2007, 36: 151.

[3] Liu C Z, Koppireddi S, Wang H, Zhang D W, Li Z T. Angew.Chem. Int. Ed., 2019, 58: 226.

[4] Chen D P, Luo R, Li M Y, Wen M Q, Li Y, Chen C, Zhang N. Chem. Commun., 2017, 53: 10930.

[5] Wang L, Hu Y J, Xu W Y, Pang Y Y, Liu F Q, Yang Y. RSC Adv., 2014, 4: 56816.

[6] Xiao Z Y, Wang W Q, Xue R Y, Zhao L, Wang L, Zhang Y H. Sci. China Chem., 2014, 57: 1731.

[7] Wen X H, Jin X N, Lv C C, Jin S E, Zheng X Q, Liu B, Wang D Q. J. Mol. Struct., 2017, 1139: 87.

[8] Metrangolo P, Neukirch H, Pilati T, Resnati G. Acc. Chem. Res., 2005, 385: 386.

[9] Britz D A, Khlobystov A N. Chem. Soc. Rev., 2006, 35: 637.

[10] Wang X P, Zhang K, Geng Y L, Sun Y X, Chen F S, Wang L. J. Mol. Struct., 2018, 1165: 106.

[11] Dai X L, Chen J M, Lu T B. Cryst. Eng. Comm., 2018, 20: 5292.

[12] Karimi-Jafari M, Padrela L, Walker G M, Croker D M. Cryst. Growth Des., 2018, 18(10): 6370.

[13] Da S C C, Martins F T. J. Mol. Struct., 2019, 1181: 157.

[14] Arunan E, Desiraju G R, Klein R A, Sadlej J, Scheiner S, Alkorta I, Clary D C, Crabtree R H, Dhannenberg J J, Hobza P, Kjaer-gaard H G, Legon A C, Mennucci B, Nesbitt D J. Pure Appl. Chem., 2011, 83: 1619.

[15] Desiraju G R. Angew. Chem. Int. Ed., 2011, 50: 52.

[16] Tan H W, Qu W W, Chen G J, Liu R Z. J. Phys. Chem. A, 2005, 109: 6303.

[17] Dong L F, Jin S W, Wang Y N, Xie X X, Liu B, Wang D Q. J. Mol. Struct., 2017, 1146: 837.

[18] Dobrowolska W S, Bator G, Sobczyk L, Grech E, Scheibe J N, Pawlukojć A, Wuttke J. J. Mol. Struct., 2010, 975: 298.

[19] Shattock T R, Arora K K, Vishweshwar P, Zaworotko M J. Cryst. Growth Des., 2008, 812: 4533.

[20] Gopi S P, Banik M, Desiraju G R. Cryst. Growth Des., 2017, 171: 308.

[21] Sreekanth B R, Vishweshwar P, Vyas K. Chem. Commun., 2007, 23: 2375.

[22] Lin Z H, Hu K K, Jin S W, Ding A H, Wang Y N, Dong L F, Gao X J, Wang D Q. J. Mol. Struct., 2017, 1146: 577.

[23] Aakeröy C ^B, Welideniya D, Desper J. Cryst. Eng. Comm., 2017, 19(1): 11.

[24] Szell P M J, Gabidullin B, Bryce D L. Acta Cryst., 2017, B73: 153.

[25] Beck T, Sheldrick G M. Acta Cryst., 2008, E64: 1286.

[26] Zhang K L, Zhang J B, Ng S W. Acta Cryst., 2011, E67: 793.

[27] Zhang K L, Diao G W, Ng S W. Acta Cryst., 2010, E66: o3165.

[28] Xing P Q, Li Q Y, Li Y Y, Wang K P, Zhang Q, Wang L. J. Mol. Struct., 2017, 1136: 59.

[29] Banik M, Gopi S P, Ganguly S, Desiraju G R. Cryst. Growth Des., 2016, 169: 5418.

[30] Gao X J, Li X L, Jin S W, Hu K K, Guo J Z, Guo M, Xu W Q, Wang D Q. J. Mol. Struct., 2018, 1155: 39.

[31] Wang L, Xue R Y, Li Y X, Zhao Y R, Liu F Q, Huang K K. Cryst. Eng. Comm., 2014, 1630: 7074.

[32] Chen C, Zhang K, Sun Y X, Xiang S G, Geng Y L, Liu K, Wang L. J. Mol. Struct., 2018, 1170: 60.

[33] Darious R S, Muthiah P T, Perdih F. Acta Cryst., 2017, C73: 743.

[34] Sheldrick G M. SHELXL-97, 1997, Göttingen: University of Göttingen.

[35] Dolomanov O V, Bourhis L J, Gildea R J, Howard J A K, Puschmann H. J. Appl. Crystallogr., 2009, 42: 339.