Synthesis and hydrogen bonded 3D polymeric structure of new compound based on 2-amino-1,4-benzene dicarboxylic acid and 4,4-bipyridine

Abstract

The new compound, [NH₂-BDC][4,4-bpy], (NH₂-BDC = 2-amino-1,4-benzene dicarboxylic acid, 4,4-bipy = 4,4-bipyridine) was synthesized and characterized by single crystal X-ray diffraction method.  The crystal structure analysis indicates that complex crystallizes in the monoclinic space group I 2/aand its asymmetric unit of contains two half2-amino-1,4-benzene dicarboxylic acid and 4,4-bipyridine molecules, which constitute a 1:1 co-crystal.  The NH₂-BDC molecule is situated on an inversion center while the 4,4-bipy molecule is situated on a twofold rotational axis.  In the crystal structure, molecules are held together via three strong intramolecular and intermolecular O–H···N and O–H···O hydrogen bonds, resulting in 3D structure.  This hydrogen-bonded polymeric network lies in the bc plane and stacks along the a axis.  Furthermore, the crystal is stabilized by weak hydrogen bond of the C–H···O type. The crystal packing exhibits p–p interactions between the aromatic rings with a centroid–centroid distance of 3.740(2) Å.  The compound, [NH₂-BDC][4,4-bpy], which is a yellow azo pigments can be used as an intermediate in industrial production.

Keywords

• 2-amino-1,4-benzene dicarboxylic acid
• 4,4-bipyridine
• crystal structure

4,4- bipiridin ve 2-amino-1,4-benzendikarboksilik asit tabanlı yeni bileşiğin sentezlenmesi ve hidrojen bağlı 3D polimerik yapısı

Abstract

Yeni bileşik, [NH₂-BDC][4,4-bpy], (NH₂-BDC = 2-amino-1,4-benzen dikarboksilik asit, 4,4-bipy = 4,4-bipiridin) sentezlendi ve tek kristal X-ışını kırınım metodu ile karakterize edildi.  Kristalin yapısal analizi bileşiğin monoklinik uzay grubu I 2/a ile kristallendiği ve asimetrik biriminin iki yarım 2-amino-1,4-benzen dikarboksilik asit ve 4,4-bipiridin molekülü içerdiğini ve yapıda 1:1 oranında kristal oluşturduğunu göstermektedir.  NH₂-BDC molekülü simetri merkezi üzerinde yer alırken 4,4-bipy molekülü iki katlı dönme ekseninde bulunmaktadır.  Kristal yapıda, moleküller üç adet kuvvetli molekül içi ve moleküler arası O–H···N ve O–H···O hidrojen bağları ile bir arada tutunurlar ve 3D kristal yapısını oluşturur.  Hidrojen bağlı polimerik ağ bc düzleminde paketlenir ve a ekseni boyunca istiflenir.  Buna ek olarak, kristal C–H···O tip zayıf hidrojen bağı ile daha kararlı hal alır.  Kristal paketlenmesinde aromatik halkaların bir merkezden diğer merkeze 3.740(2) Å uzaklığa sahip p–p etkileşmelerinin olduğu görülür.  Sarı renkli azot pigmentlerinden olan [NH₂-BDC][4,4-bpy] bileşiği endüstriyel üretimde bir ara madde olarak kullanılabilir. 

Keywords

• 2-amino-1 4-benzene dicarboxylic acid
• 4 4-bipyridine
• kristal yapı

References

1. Loos, S., Seichter, W., Weber, E. ve Mertens, F., 2-Aminoterephthalic acid N,N Dimethylformamide disolvate, Acta Crystallographica Section E, E68, 2501-2508, (2012).
2. Brüning, J., Bats, J.W. ve Schmidt, M.U., 2-Aminoterephthalic acid dimethyl ester, Acta Crystallographica Section E, E65, 2468-2469, (2009).
3. Zhang, W.X., Liao, P.Q., Lin, R.B., Wei, Y.S., Zeng, M.H. ve Chen, X.M., Metal cluster-based functional porous coordination polymers, Coordination Chemistry Reviews, 293-294, 263-268, (2015).
4. Yabing, H., Wei, Z., Guodong, Q. ve Banglin, C., Methane storage in metal–organic frameworks, Chemical Society Reviews, 43, 5657, (2014).
5. Qiu, S.L. ve Zhu, G.S., Molecular engineering for synthesizing novel structures of metal–organic frameworks with multifunctional properties, Coordination Chemistry Reviews, 253, 2891–2911, (2009).
6. Sen, I., Kara, H. ve Azizoglu, A., Substituent effects on hydrogen bonding of aromatic amide-carboxylate, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 167, 50-58, (2016).
7. Coban, M.B., Kocak, C., Kara, H., Aygun, M. ve Amjad, A., Magnetic properties and sensitized visible and NIR luminescence of Dy-III and Eu-III coordination polymers by energy transfer antenna ligands, Molecular Crystals and Liquid Crystals, 648, 202-215, (2017).
8. Coban, M.B., Amjad, A., Kara, H. ve Aygun, M., Sensitization of Ho-III and Sm-III luminescence by efficient energy transfer from antenna ligands: Magnetic, visible and NIR photoluminescence properties of Gd-III, Ho-III and Sm-III coordination polymers, Inorganica Chimica Acta, 455, 25-33, (2017).

9. SMART, Copyright 1989–1999, Bruker AXS, Madison, WI, USA; SAINT, Bruker AXS, Madison, WI, USA.
10. Sheldrick, G.M., A short history of SHELX, Acta Crystallographica Section A Foundations and Advances, 64, 112–122, (2008).
11. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K. ve Puschmann, H., OLEX2: A complete structure solution, refinement and analysis program, Journal of Applied Crystallography, 42, 339–341, (2009).
12. Spek, A.L., Structure validation in chemical crystallography, Acta Crystallographica Section D Biological Crystallography, 65,148–155, (2009).