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Vol. 30 No. 9 (2018): Vol 30 Issue 9

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Single Crystal XRD and Quantum Chemical Studies on Non-Proton Transfer Co-Crystals of 2-Amino-5-nitropyridine with Phenylthioacetic Acid and Barbituric Acid

https://doi.org/10.14233/ajchem.2018.21482
V. Velmurugan
Department of Chemistry, Manonmaniam Sundaranar University, Abishekapatti, Tirunelveli-627 012, India
S. Kumaresan
Department of Chemistry, Manonmaniam Sundaranar University, Abishekapatti, Tirunelveli-627 012, India
B. Ravindran Durai Nayagam
Department of Chemistry, Pope’s College, Sawyerpuram-628 251, India
N. Bhuvanesh
Department of Chemistry, Texas A & M University, College Station, Texas-77842, U.S.A.
S. Athimoolam
Department of Physics, University College of Engineering, Anna University, Nagercoil-629004, India
P. Palanisamy
Department of Chemistry, Pioneer Kumaraswamy College, Nagercoil-629 003, India

Corresponding Author(s) : S. Kumaresan

skumarmsu@yahoo.com

Asian Journal of Chemistry, Vol. 30 No. 9 (2018): Vol 30 Issue 9

Abstract

New co-crystals of 2-amino-5-nitropyridine with phenylthioacetic acid or barbituric acid have been grown by gradual evaporation approach under room temperature. The molecular structures of the present compounds were resolved by single crystal X-ray diffraction. The vibration spectral measurement was carried out using FT-IR spectroscopy. The X-ray studies show that the crystal packing is control by N–H···O and O–H···N for 2-amino-5-nitropyridine: phenylthioacetic acid (2A5NPPTAA) and N–H···O and N–H···N for 2-amino-5-nitropyridine: barbituric acid (2A5NPBBA), intermolecular hydrogen bonds leading to hydrogen bonded co-crystal. In 2A5NPPTAA, 2-amino 5-nitropyridine (2A5NP) is linked with carboxyl group in phenylthioacetic acid (PTAA) through N–H···O intermolecular hydrogen bond to form ring R22(8) motifs. The N–H···O and O–H···N intermolecular hydrogen bonds are leading to a ring R44(8) motif. These ring motifs lead to the hydrophilic layers at z = 0 and 1 which are intermediate between the hydrophobic layer at 1/2. In the 2A5NPBBA, the N–H···O and N–H···N intermolecular hydrogen bonds form a heterosynthon of two R22(8) motifs. This ring motif is connected with nitro group in 2-amino-5-nitropyridine by N–H···O hydrogen bond to form a rare bifurcated ring R34(8) motif. These two ring motifs are further linked in barbituric (BBA) acid via N–H···O hydrogen bond to form R33(12) motifs. This molecular aggregations lead parallel to the 202 and`20`2 crystallographic smooth making strong intensity peaks for these plain on X-ray diffraction. Computative optimizations of the molecules were done by density functional theory (DFT) using the B3LYP function and Hartree-Fock (HF) level with 6-311++G(d,p) basis set. The enhance molecular division and computed vibration spectrum are approximate experiment results which display express accepting.

Keywords

2-Amino-5-nitropyridine Phenylthioacetic acid Barbituric acid Co-crystal
Velmurugan, V., Kumaresan, S., Durai Nayagam, B. R., Bhuvanesh, N., Athimoolam, S., & Palanisamy, P. (2018). Single Crystal XRD and Quantum Chemical Studies on Non-Proton Transfer Co-Crystals of 2-Amino-5-nitropyridine with Phenylthioacetic Acid and Barbituric Acid. Asian Journal of Chemistry, 30(9), 2116–2128. https://doi.org/10.14233/ajchem.2018.21482
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