Theoretical Calculations in Gas and Solid Phase on The Tautomeric Structure of 3-[(E)-2-(4-phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]-indolin-2-one

Year 2020, , 96 - 102, 17.03.2020

Tuncay Karakurt

https://doi.org/10.35414/akufemubid.534697

Cited By: 2

Abstract

In this study, theoretical calculations were made on two tautomer forms of the thiazole containing compound 3-[(E)-2-(4-phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]-indolin-2-one in gas and solid phase under the periodic boundary conditions. For the two tautomer forms, some geometric parameters of the molecule and the molecular orbital energies of the frontier (FMO) have been investigated using Gaussian 09 program with the DFT/B3LYP/6-31G(d) method in the gas phase and with Quantum-Espresso package program using periodic boundary conditions (PBC) in the solid. In addition, the tautomer structures were compared by IRC (Intrinsic Reaction Coordinate) analysis method. All theoretical studies were performed for two tautomeric structures. As a consequence, all calculations show that stable structure of the title compound is compatible with the structure obtained by X-rays in both gas and solid phase.

Keywords

Gaussian 09, PBC, DFT, Quantum-Espresso

3-[(E)-2-(4-fenil-1,3-tiyazol-2-yl)hidrazin-1-yiliden]-indolin-2-on Bileşiğinin Tautomer Yapısı Üzerinde Gaz ve Katı Fazında Teorik Hesaplamalar

Abstract

Tiyazol halkası içeren 3-[(E)-2-(4-fenil-1,3-tiyazol-2-yl)hidrazin-1-yiliden]-indolin-2-on bileşiğinin iki tautomer formu üzerinde gaz ve katı fazında hesaplamalar yapılmıştır. İki tautomer yapı için gaz fazında Gaussian 09 programı ile DFT/B3LYP/6-31G(d) metodu, katı fazında ise Quantum-Espresso paket programı ile periyodik sınır şartları (PBC) kullanılarak molekülün geometriksel parametreleri ve frontier moleküler orbital enerjileri (FMO) incelenmiştir. Ayrıca tautomer yapılar, IRC (Intrinsic Reaction Coordinate) analiz yöntemi ile de karşılaştırılmıştır. Teorik tüm çalışmalar iki tautomer yapı üzerinde yapılmış olup bileşiğin hem gaz hem de katı fazında hesaplanan kararlı yapılarının x-ışınları yöntemiyle elde edilen yapıyla uyumlu olduğu görülmüştür.

Keywords

Gaussian 09, PBC;, DFT, Quantum-Espresso

References

• Atkins P.W., 1992. The elements of physical chemistry (Oxford University Press Oxford United Kingdom).
• Becke A.D., 1993. Density‐functional thermochemistry. III. The role of exact exchange, The Journal of Chemical Physics, 98, 5648-52.
• Dennington R., Keith, T. and Millam, J., 2009. GaussView, version 5, Semichem Inc., Shawnee Mission, KS.
• Frisch M., Trucks, G., Schlegel, H.B., Scuseria, G., Robb, M., Cheeseman, J., Scalmani, G., Barone, V., Mennucci, B. and Petersson, G., 2009. Gaussian 09, revision a. 02, gaussian, Inc., Wallingford, CT, 200.
• Foresman J.B., Frisch A.,1996. Exploring chemistry with electronic structure methods: a guide to using Gaussian.
• Giannozzi P., Baroni S., Bonini N., Calandra M., Car R., CavazzoniC ., Ceresoli D., Chiarotti G.L., Cococcioni M., Dabo I.,2009. QUANTUM ESPRESSO: a modular and open-source software project for quantum simulations of materials, Journal of physics: Condensed matter, 21, 39.
• Hadjipavlou-Litina D., and Geronikaki A., 1996. Anti-inflammatory activity of some novel 1-[3-(aroylo)] and one 1-[3-(aryloxy)]-propyl aminothiazole in correlation with structure and lipophilicity, Arzneimittel-Forschung 46, 805-08.
• Halasangi B.M., Badami P.S., Patil S.A., and Kumar G.N.A., 2014. Crystal structure of 3-[( E)-2-(4-phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]-indolin-2-one, Acta Crystallography E, E70, o1177-o78
• Hohenberg P., and Kohn W., 1964. Inhomogeneous electron gas, Physical review 136, B864.
• Holla B.S., Malini K., Rao B.S., Sarojini B., and Kumari N.S., 2003. Synthesis of some new 2, 4-disubstituted thiazoles as possible antibacterial and anti-inflammatory agents, European Journal of Medicinal Chemistry 38, 313-18.
• Jarahpour A., Motamedifar M., Pakshir K., Hadi N., and Zarei M., 2004. Synthesis of novel azo Schiff bases and their antibacterial and antifungal activities, Molecules, 10, 815-24.
• Karakurt T., 2018. Investigation of the molecular structure of 4-(3methyl-3phenylcyclobutyl)-2-[2-(3 methylbenzylidene)hydrazinyl]thiazole in the gas and solid phases, Acta C Crystal, C74, 1502-08.
• Karakurt T., Cukurovali A., Subasi N.T., Onaran, A., Ece A., Eker S. and Kani I.,2018. Experimental and theoretical studies on tautomeric structures of a newly synthesized 2, 2’(hydrazine-1, 2-diylidenebis (propan-1-yl-1-ylidene)) diphenol. Chemical Physics Letters, 693, 132.
• Kohn W., and Sham L.J., 1965. Self-consistent equations including exchange and correlation effects Phys Rev, 140, A1133.
• Kutter E., Machleidt H., Reuter W., Sauter R., and Wildfeue A., 1972. Comparative in vitro and in vivo Structure-Activity Studies of Antiparasitic 2-Methyleneamino-5-nitrothiazoles. ACS Publications.
• Lee C., Yang, W., and Parr, R.G., 1988. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Physical review B, 37, 785.
• Nagatomi H., and Ando K., 1984. Studies on the anti-inflammatory activity and ulcerogenic adverse effect of thiazole derivatives, especially 2-amino-thiazoleacetic acid derivatives, Arzneimittelforschung, 34, 599-603
• Shyam R., and Tiwari I., 1975. Studies on Some New Thiazolidones as Potential Fungicides,Agric Biol Chem, 39, 715-17.
• Perdew J.P., and Zunger A., 1981. Self-interaction correction to density-functional approximations for many-electron systems Phys Rev B23, 5048.
• Zolinger H., 1991. Color chemistry, synthesis, properties ans application of organic dyes and pigments, 2nd Edn.