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X-Ray and Theoretical Studies of 4-((4-(tert-butyl)benzylidene)amino)-1,5-dimethyl-2- phenyl-1,2-dihydro-3H-pyrazol-3-one

Year 2018, , 108 - 120, 30.11.2018
https://doi.org/10.29233/sdufeffd.466722

Abstract

The molecular structure of [4-((4-(tert-butyl)benzylidene)amino)-1,5-dimethyl-2-phenyl1,2-dihydro-3H-pyrazol-3-one
crystal and some physical and chemical properties were investigated
using single crystal X-ray diffraction, FT-IR, UV and quantum mechanical methods. The compound
studied in this study is the Schiff base compound and crystalizes in monoclinic space group I2/a. The
molecule is not planar. The crystal structure is stabilized by intermolecular C-H…..π interactions.
Theoretically, it was investigated using Density Functional Theory (DFT) and Hartree-Fock Roothann
Method compared with the experimental results and it was seen that both results were in agreement
with each other. In the DFT and HF calculations, the B3LYP / 6-31G +d base set and Berny's method
were used

References

  • P. Przybylski, A. Huczynski, K. Pyta, B. Brzezinski, and F. Bartl, "Biological Properties of Schiff Bases and Azo Derivatives of Phenols," Curr. Org. Chem., vol. 13, no. 2, pp. 124-148, Jan 2009.
  • A. Osowole and E. Akpan, "Synthesis spectroscopic characterisation, in-vitro anticancer and antimicrobial activities of some metal (II) complexes of 3-{4, 6-dimethoxy pyrimidinyl) iminomethyl naphthalen-2-ol," Eur. J. Appl. Sci, vol. 4, pp. 14-20, 2012.
  • M. Suresh and V. Prakash, "Preparation and characterization of Cr (III), Mn (II), Co (III), Ni (II), Cu (II), Zn (II) and Cd (II) chelates of schiffs base derived from vanillin and 4-amino antipyrine," Int. J. Phys. Sci., vol. 5, no. 14, pp. 2203-2211, 2010.
  • Z. M. Bedeui, "Synthesis And Characterization Of Schiff-Base Ligand Derivative From 4-Aminoantipyrine And Its Transition Metal Complexes," Journals kufa for chamical, no. 8, pp. 70-78, 2013.
  • A. K. Singh, G. Saxena, R. Prasad, and A. Kumar, "Synthesis, characterization and calculated non-linear optical properties of two new chalcones," J. Mol. Struct., vol. 1017, pp. 26-31, 2012.
  • L. Guo, S. Hong, X. Lin, Z. Xie, and G. Chen, "An organically modified sol–gel membrane for detection of lead ion by using 2-hydroxy-1-naphthaldehydene-8-aminoquinoline as fluorescence probe," Sensor. Actuat. B-Chem., vol. 130, no. 2, pp. 789-794, 2008.
  • N. Raman, J. D. Raja, and A. Sakthivel, "Synthesis, spectral characterization of Schiff base transition metal complexes: DNA cleavage and antimicrobial activity studies," J. Chem. Sci., vol. 119, no. 4, pp. 303-310, 2007.
  • M. S. Alam, D.-U. Lee, and M. L. Bari, "Antibacterial and cytotoxic activities of Schiff base analogues of 4-aminoantipyrine," J. Korean Soc. Appl. Bi., vol. 57, no. 5, pp. 613-619, 2014.
  • Stoe and X. Cie, "Area (Version 1.18) and X-Red32 (Version 1.04)," Stoe&Cie, Darmstadt, Germany, 2002.
  • G. M. Sheldrick, "A short history of SHELX," Acta. Crystallogr. Section. A., vol. 64, no. 1, pp. 112-122, 2008.
  • G. M. Sheldrick, "Crystal structure refinement with SHELXL," Acta. Crystallogr. C., vol. 71, no. 1, pp. 3-8, 2015.
  • L. J. Farrugia, "WinGX and ORTEP for Windows: an update," Journal of Applied Crystallography, vol. 45, no. 4, pp. 849-854, 2012.
  • M.J.Frisch, G.W.Trucks, H.B. Schlegel, G.E.Scuseria, M. A. Robb, J. R. Cheeseman, et al. “Gaussian 03, Revision E. 01. Gaussian Inc.”, Wallingford CT 2004.
  • A. Frisch, R. II Dennington, T. Keith, J. Millam, A.B. Nielsen, A.J. Holder, et al. "GaussView reference, version 4.0. Gaussian Inc.", Pittsburgh. 2007.
  • C. Lee, W. Yang, and R. G. Parr, "Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density," Phys. Rev. B., vol. 37, no. 2, p. 785, 1988.
  • A. Becke, "Density-functional thermochemistry. III. The role of exact exchange," J. Chem. Phys., vol. 98, no. 7, p. 5648, 1993.
  • P. Politzer, J. S. Murray, and M. C. Concha, "The complementary roles of molecular surface electrostatic potentials and average local ionization energies with respect to electrophilic processes," International Journal of Quantum Chemistry, vol. 88, no. 1, pp. 19-27, 2002.
  • N. Okulik and A. H. Jubert, "Theoretical analysis of the reactive sites of non-steroidal anti-inflammatory drugs," Internet Electronic Journal of Molecular Design, vol. 4, no. 1, pp. 17-30, 2005.
  • F. J. Luque, J. M. López, and M. Orozco, "Perspective on “Electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects”," Theor. Chem. Acc., vol. 103, no. 3-4, pp. 343-345, 2000.
  • E. Scrocco and J. Tomasi, "Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials," in Advances in quantum chemistry, vol. 11: Elsevier, 1978, pp. 115-193.
  • G. Socrates, "Infrared Characteristic Group Frequencies, J," John Wily & Sons, NY, p. 115, 1980.
  • H. Bülbül, Y. Köysal, N. Dege, S. Gümüş, and E. Ağar, "Crystal structure, spectroscopy, SEM analysis, and computational studies of N-(1, 3-Dioxoisoindolin-2yl) benzamide," Journal of Crystallography, vol. 2015, Artcile id 232036 (6 p.), 2015.
  • M. Evecen, H. Tanak, Y. Ünver, F. Çelik, and L. Semiz, "Analysis on molecular, spectroscopic and electronic behavior of 4, 4'-(butane-1, 4-diyl) bis (1-((1-(4-chlorobenzyl)-1H-1, 2, 3-triazol-5-yl) methyl)-3-methyl-1H-1, 2, 4-triazol-5 (4H)-one): A theoretical approach," J. Mol. Struct., vol. 1174, pp. 60-66, 2018.

4 - ((4- (tert-bütil) benziliden) amino)-1,5-dimetil-2-fenil-1,2-dihidro-3H-pirazol-3-on’un X-ışını ve Teorik Çalışmaları

Year 2018, , 108 - 120, 30.11.2018
https://doi.org/10.29233/sdufeffd.466722

Abstract

[4-((4-(tert-bütil) benziliden) amino)-1,5-dimetil-2-fenil-1,2-dihidro-3H-pirazol-3-on kristalinin
moleküler yapısı ve bazı fiziksel ve kimyasal özellikleri tek kristal X-ışını kırınımı, FT-IR, UV ve
kuantum mekaniksel yöntemleri kullanılarak araştırıldı. Bu çalışmada incelenen bileşik Schiff bazı
bileşiktir ve bileşik monoklinik kristal sisteminde kristalleşmiştir, uzay grubu ise I2/ a'dır. Molekül
düzlemsel değildir. Kristal yapı moleküller arası C-H…π etkileşimleri ile stabilize edilmiştir. Teorik
olarak, Yoğunluk Fonksiyonel Kuramı (YFK) ve Hartree-Fock Roothann (HF) yöntemi kullanılarak
araştırılmış ve deneysel sonuçları ile karşılaştırılması yapılmıştır. Yapılan hesaplamalar sonucunda bu
iki teorik hesaplama sonucunun deneysel sonuçlar ile örtüştüğü gözlendi. YFK ve HF yöntemi
hesaplamalarında B3LYP / 6-31G +d baz seti ve Berny yöntemi kullanıldı

References

  • P. Przybylski, A. Huczynski, K. Pyta, B. Brzezinski, and F. Bartl, "Biological Properties of Schiff Bases and Azo Derivatives of Phenols," Curr. Org. Chem., vol. 13, no. 2, pp. 124-148, Jan 2009.
  • A. Osowole and E. Akpan, "Synthesis spectroscopic characterisation, in-vitro anticancer and antimicrobial activities of some metal (II) complexes of 3-{4, 6-dimethoxy pyrimidinyl) iminomethyl naphthalen-2-ol," Eur. J. Appl. Sci, vol. 4, pp. 14-20, 2012.
  • M. Suresh and V. Prakash, "Preparation and characterization of Cr (III), Mn (II), Co (III), Ni (II), Cu (II), Zn (II) and Cd (II) chelates of schiffs base derived from vanillin and 4-amino antipyrine," Int. J. Phys. Sci., vol. 5, no. 14, pp. 2203-2211, 2010.
  • Z. M. Bedeui, "Synthesis And Characterization Of Schiff-Base Ligand Derivative From 4-Aminoantipyrine And Its Transition Metal Complexes," Journals kufa for chamical, no. 8, pp. 70-78, 2013.
  • A. K. Singh, G. Saxena, R. Prasad, and A. Kumar, "Synthesis, characterization and calculated non-linear optical properties of two new chalcones," J. Mol. Struct., vol. 1017, pp. 26-31, 2012.
  • L. Guo, S. Hong, X. Lin, Z. Xie, and G. Chen, "An organically modified sol–gel membrane for detection of lead ion by using 2-hydroxy-1-naphthaldehydene-8-aminoquinoline as fluorescence probe," Sensor. Actuat. B-Chem., vol. 130, no. 2, pp. 789-794, 2008.
  • N. Raman, J. D. Raja, and A. Sakthivel, "Synthesis, spectral characterization of Schiff base transition metal complexes: DNA cleavage and antimicrobial activity studies," J. Chem. Sci., vol. 119, no. 4, pp. 303-310, 2007.
  • M. S. Alam, D.-U. Lee, and M. L. Bari, "Antibacterial and cytotoxic activities of Schiff base analogues of 4-aminoantipyrine," J. Korean Soc. Appl. Bi., vol. 57, no. 5, pp. 613-619, 2014.
  • Stoe and X. Cie, "Area (Version 1.18) and X-Red32 (Version 1.04)," Stoe&Cie, Darmstadt, Germany, 2002.
  • G. M. Sheldrick, "A short history of SHELX," Acta. Crystallogr. Section. A., vol. 64, no. 1, pp. 112-122, 2008.
  • G. M. Sheldrick, "Crystal structure refinement with SHELXL," Acta. Crystallogr. C., vol. 71, no. 1, pp. 3-8, 2015.
  • L. J. Farrugia, "WinGX and ORTEP for Windows: an update," Journal of Applied Crystallography, vol. 45, no. 4, pp. 849-854, 2012.
  • M.J.Frisch, G.W.Trucks, H.B. Schlegel, G.E.Scuseria, M. A. Robb, J. R. Cheeseman, et al. “Gaussian 03, Revision E. 01. Gaussian Inc.”, Wallingford CT 2004.
  • A. Frisch, R. II Dennington, T. Keith, J. Millam, A.B. Nielsen, A.J. Holder, et al. "GaussView reference, version 4.0. Gaussian Inc.", Pittsburgh. 2007.
  • C. Lee, W. Yang, and R. G. Parr, "Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density," Phys. Rev. B., vol. 37, no. 2, p. 785, 1988.
  • A. Becke, "Density-functional thermochemistry. III. The role of exact exchange," J. Chem. Phys., vol. 98, no. 7, p. 5648, 1993.
  • P. Politzer, J. S. Murray, and M. C. Concha, "The complementary roles of molecular surface electrostatic potentials and average local ionization energies with respect to electrophilic processes," International Journal of Quantum Chemistry, vol. 88, no. 1, pp. 19-27, 2002.
  • N. Okulik and A. H. Jubert, "Theoretical analysis of the reactive sites of non-steroidal anti-inflammatory drugs," Internet Electronic Journal of Molecular Design, vol. 4, no. 1, pp. 17-30, 2005.
  • F. J. Luque, J. M. López, and M. Orozco, "Perspective on “Electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects”," Theor. Chem. Acc., vol. 103, no. 3-4, pp. 343-345, 2000.
  • E. Scrocco and J. Tomasi, "Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials," in Advances in quantum chemistry, vol. 11: Elsevier, 1978, pp. 115-193.
  • G. Socrates, "Infrared Characteristic Group Frequencies, J," John Wily & Sons, NY, p. 115, 1980.
  • H. Bülbül, Y. Köysal, N. Dege, S. Gümüş, and E. Ağar, "Crystal structure, spectroscopy, SEM analysis, and computational studies of N-(1, 3-Dioxoisoindolin-2yl) benzamide," Journal of Crystallography, vol. 2015, Artcile id 232036 (6 p.), 2015.
  • M. Evecen, H. Tanak, Y. Ünver, F. Çelik, and L. Semiz, "Analysis on molecular, spectroscopic and electronic behavior of 4, 4'-(butane-1, 4-diyl) bis (1-((1-(4-chlorobenzyl)-1H-1, 2, 3-triazol-5-yl) methyl)-3-methyl-1H-1, 2, 4-triazol-5 (4H)-one): A theoretical approach," J. Mol. Struct., vol. 1174, pp. 60-66, 2018.
There are 23 citations in total.

Details

Primary Language English
Subjects Metrology, Applied and Industrial Physics
Journal Section Makaleler
Authors

Şehriman Atalay

Publication Date November 30, 2018
Published in Issue Year 2018

Cite

IEEE Ş. Atalay, “X-Ray and Theoretical Studies of 4-((4-(tert-butyl)benzylidene)amino)-1,5-dimethyl-2- phenyl-1,2-dihydro-3H-pyrazol-3-one”, Süleyman Demirel University Faculty of Arts and Science Journal of Science, vol. 13, no. 2, pp. 108–120, 2018, doi: 10.29233/sdufeffd.466722.