Benzotiyazol ve 1,3,4-Tiyadiazol İçeren Tek Kristalin Sentezi ve Teorik Olarak İncelenmesi

Year 2019, , 2105 - 2116, 01.12.2019

Tuncay Karakurt , Hakan Tahtacı , Mustafa Er

https://doi.org/10.21597/jist.545085

Abstract

Bu çalışmada tiyadiazol ve benzotiyazol halkası içeren 3-((5-amino-1,3,4-tiyadiazol-2-il)metil)benzo[d]tiyazol-2(3H)-on bileşiğinin yapısı, X-ışını kırınım yöntemi ve IR, NMR spektroskopik yöntemler kullanılarak aydınlatılmıştır. Deneysel çalışmalara destek olması amacı ile de B3LYP metodu ve 6-31G(d,p) temel seti kullanılarak teorik çalışmalar yapılarak bazı yapısal parametreler hesaplanmıştır. Özellikle kristalin reaktif bölgelerini incelemek için kısmi atom yükü ve moleküler elektrostatik potansiyel (MEP) ve Hirshfeld yüzey analizleri yapıldı. Son olarak da AIM yük analizi kullanılarak moleküller arası etkileşimlerin özellikleri incelenmiştir. Hesaplanan sonuçların, X-ışını verileriyle uyumlu olduğu görülmüştür.

Keywords

Benzotiyazol, X-ışını, MEP, Hirshfeld, AIM

Supporting Institution

Kırşehir Ahi Evran Üniversitesi

Project Number

MMF.A4.18.011

Thanks

Bu çalışma, Kırşehir Ahi Evran Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimince Desteklenmiştir (Proje Numarası: MMF.A4.18.011).

Experimental and Theoretical Investigation of Single Crystal Containing Benzothiazole and Thiadiazole

Abstract

In this study, the structure of 3-((5-amino-1,3,4-thiadiazol-2-yl) methyl) benzo[d]thiazol-2(3H)-one containing thiadiazole and benzothiazole ring were characterized using X-ray diffraction and IR, NMR spectroscopic methods. In order to support experimental studies, some structural parameters have been calculated by using B3LYP method and 6-31G(d, p) basic set. In particular, partial atomic charge and molecular electrostatic potential (MEP) and Hirshfeld surface analyzes were performed to examine the crystalline reactive regions. Finally, the properties of intermolecular interactions were investigated using AIM charge analysis. It was observed that the calculated results were consistent with X-ray data.

Keywords

Benzothiazole, X-ray, MEP, Hirshfeld, AIM

Project Number

MMF.A4.18.011

References

• Alam MS, Lee D-U, 2017. Spectral (FT-IR, FT-Raman, UV, and fluorescence), DFT, and solid state interaction analyses of (E)-4-(3, 4-dimethoxybenzylideneamino)-1, 5-dimethyl-2-phenyl-1H-pyrazol-3 (2H)-one. Journal of Molecular Structure, 1128: 174-185.
• Asati V, Sahu NK, Rathore A, Sahu S, Kohli D, 2015. Synthesis, characterization and antimicrobial evaluation of some 1, 3-benzothiazole-2-yl-hydrazone derivatives. Arabian Journal of Chemistry, 8: 495-499.
• Bader RF, 2006. Pauli repulsions exist only in the eye of the beholder. Chemistry–A European Journal, 12: 2896-2901.
• Becke AD, 1993. Density‐functional thermochemistry. III. The role of exact exchange. The Journal of Chemical Physics, 98: 5648-5652.
• Bruker A, 2008. APEX2, V2008. 6, SADABS V2008/1, SAINT V7. 60A, SHELXTL V6. 14. Bruker AXS Inc., Madison, Wisconsin, USA.
• Dennington R, Keith T, Millam J, 2009. GaussView, version 5. Semichem Inc., Shawnee Mission, KS.
• DEsai K, Baxi A, 1993. Studies on 2-azetidinone: part-vi synthesis and antimicrobial activity of 5-(2', 4'-dichloro phenoxy methyl)-2-(4. Indian Journal of Pharmaceutical Sciences, 55.
• Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JA, Puschmann H, 2009. OLEX2: a complete structure solution, refinement and analysis program. Journal of Applied Crystallography, 42: 339-341.
• Ece A, Sevin F, 2013. The discovery of potential cyclin A/CDK2 inhibitors: a combination of 3D QSAR pharmacophore modeling, virtual screening, and molecular docking studies. Medicinal chemistry research, 22: 5832-5843.
• Er M, Isildak G, Tahtaci H, Karakurt T, 2016. Novel 2-amino-1, 3, 4-thiadiazoles and their acyl derivatives: Synthesis, structural characterization, molecular docking studies and comparison of experimental and computational results. Journal of Molecular Structure, 1110: 102-113.
• Er M, Şahin A, Tahtacı H, 2014. Synthesis and characterization of novel 1, 3-thiazole and 2-amino-1, 3, 4-thiadiazole derivatives. Macedonian Journal of Chemistry and Chemical Engineering, 33: 189-198.
• Espinosa E, Molins E, Lecomte C, 1998. Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities. Chemical physics letters, 285: 170-173.
• Foresman JB, Frisch A, 1996. Exploring chemistry with electronic structure methods: a guide to using Gaussian.
• Frisch M, Trucks G, Schlegel HB, Scuseria G, Robb M, Cheeseman J, Scalmani G, Barone V, Mennucci B, Petersson G, 2009. Gaussian 09, revision a. 02, gaussian. Inc., Wallingford, CT, 200.
• Gabr MT, El-Gohary NS, El-Bendary ER, El-Kerdawy MM, 2014. Synthesis and in vitro antitumor activity of new series of benzothiazole and pyrimido [2, 1-b] benzothiazole derivatives. European journal of medicinal chemistry, 85: 576-592.
• Keith TA, 2015. AIMAll (Version 14.11. 23), TK Gristmill Software, Overland Park KS, USA, 2014.
• Lee C, Yang W, Parr RG, 1988. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical review B, 37: 785.
• Lindgren EB, de Brito MA, Vasconcelos TR, de Moraes MO, Montenegro RC, Yoneda JD, Leal KZ, 2014. Synthesis and anticancer activity of (E)-2-benzothiazole hydrazones. European journal of medicinal chemistry, 86: 12-16.
• Luque FJ, López JM, Orozco M, 2000. Perspective on “Electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects”. Theoretical Chemistry Accounts, 103: 343-345.
• Mascarenhas NM, Ghoshal N, 2008. An efficient tool for identifying inhibitors based on 3D-QSAR and docking using feature-shape pharmacophore of biologically active conformation–A case study with CDK2/CyclinA. European journal of medicinal chemistry, 43: 2807-2818.
• Murray JS, Sen K. (1996). Molecular electrostatic potentials: concepts and applications. Elsevier.
• Noolvi MN, Patel HM, Kamboj S, Cameotra SS, 2016. Synthesis and antimicrobial evaluation of novel 1, 3, 4-thiadiazole derivatives of 2-(4-formyl-2-methoxyphenoxy) acetic acid. Arabian Journal of Chemistry, 9: S1283-S1289.
• Rozas I, Alkorta I, Elguero J, 2000. Behavior of ylides containing N, O, and C atoms as hydrogen bond acceptors. Journal of the American Chemical Society, 122: 11154-11161.
• Sheldrick GM, 2015a. Crystal structure refinement with SHELXL. Acta Crystallographica Section C: Structural Chemistry, 71: 3-8.
• Sheldrick GM, 2015b. SHELXT–Integrated space-group and crystal-structure determination. Acta Crystallographica Section A: Foundations and Advances, 71: 3-8.
• Spackman MA, Jayatilaka D, 2009. Hirshfeld surface analysis. CrystEngComm, 11: 19-32.
• Tang J, Liu J, Wu F, 2016. Molecular docking studies and biological evaluation of 1, 3, 4-thiadiazole derivatives bearing Schiff base moieties as tyrosinase inhibitors. Bioorganic chemistry, 69: 29-36.
• Torabi Farkhani E, Pourayoubi M, Izadyar M, Andreev PV, Shchegravina ES, 2018. Evaluation of N—H⋯ S and N—H⋯ π interactions in O, O′-diethyl N-(2, 4, 6-trimethylphenyl) thiophosphate: a combination of X-ray crystallographic and theoretical studies. Acta Crystallographica Section C: Structural Chemistry, 74.
• Turner M, McKinnon J, Wolff S, Grimwood D, Spackman P, Jayatilaka D, Spackman M, 2017. CrystalExplorer17. University of Western Australia.
• Yadav P, Devprakash SG, Senthilkumar G, 2011. Benzothiazole: different methods of synthesis and diverse biological activities. International journal of pharmaceutical sciences and drug research, 3: 01-07.