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Schiff Bazlı İndazol Bileşiğinin Yapı Karakterizasyonu ve Kuramsal Hesaplamalarla İncelenmesi

Year 2024, , 472 - 482, 23.12.2024
https://doi.org/10.19113/sdufenbed.1523523

Abstract

Özet: (E)-4-Metoksi-2-(((4-metoksi-1H-indazol-3-il)imino)metil)fenol bileşiği IR, Uv-Vis, 13C-NMR / 1H-NMR ve X-ışını kırınımı yöntemleri kullanılarak yapısal karakterizasyonu yapıldı ve bileşik yapısının enol-imin formunda şekillendiği belirlendi. Moleküler yapının 3-boyutlu yüzey özelliklerini görselleştirmek için Hirshfeld yüzey analizi kullanıldı. Moleküler yapının kuramsal özelliklerinin belirlenmesinde Yoğunluk Fonksiyonel Teorisi’nin 6-311G(d,p) baz setinden yararlanıldı. Başlık bileşiğinin UV-Vis spektrumları DMSO içinde 5x10-5 M konsantrasyonda hazırlandı. 13C-NMR ve 1H-NMR karakterizasyon analizleri deneysel ve kuramsal olarak karşılaştırmalı olarak verildi. Kuramsal hesaplamalar yardımıyla moleküler yapının elektrofilik doğası, nükleofilik doğası, kimysal aktiviteleri hakkında ayrıntılı çalışmalar yapıldı. Bu çalışmalar sonucunda frontier moleküler orbitallar, sertlik, yumaşaklık, mulliken popülasyon analiz yükleri, MEP ve kontür yüzeyleri hakkında bilgilere ulaştık. Ek olarak, DNA temel yapı taşları olan adenin, sitozin, guanin ve timin bazları ile moleküler yapımızı kuramsal olarak birleştirdik ve hesaplamlar yaptık. Bu hesaplamalar sonucunda moleküler yapının yük transferini ve elektrofilik ve nükleofilik doğasını araştımak için ECT (elektrofilik tabanlı yük transferi) yöntemi ve DN (yük transferi) kullanıldı.

Ethical Statement

Bu çalışmanın yazarları olarak herhangi bir “Etik Kurul Onayı” ve/veya “Aydınlatılmış Onam Bilgileri” beyanımız bulunmadığını bildiririz.

Project Number

PYO.FEN.1904.22.026

References

  • [1] Schiff, H. 1864. Mittheilungen aus dem Universitatslaboratorium in ¨ Pisa: eine neue reihe organischer Basen. Justus Liebigs Annalen der Chemie, 131, 1, 118–119.
  • [2] Dominiak, P. M., Grech, E., Barr, G., Teat, S., Mallinson, P., Wozniak, K., 2003. Neutral and ionic hydrogen bonding in Schiff bases. Chem. Eur. J., 9(4), 963- 970.
  • [3] Güzel, E., Macit, M., Ergüzeloğlu, E., Kalecik, S., Keleşoğlu, Z., & Yavuz, M. 2023. Two new Schiff bases of (E)-2, 4-di-tert-butyl-6-((4-fluorophenylimino) methyl) phenol (I) and (E)-2, 4-di-tert-butyl-6-((3-iodo-4-methylphenylimino) methyl) phenol (II): structural, spectroscopic and quantum chemical calculations. Molecular Crystals and Liquid Crystals, 763(1), 96-113.
  • [4] Fischer, E. 1884. Phenylhydrazin als reagens auf aldehyde und ketone. Berichte der deutschen chmemischen ,Gesellschaft.
  • [5] Denya, S.F., Malan, J. 2018. Joubert, Indazole derivatives and their therapeutic applications: a patent review (2013-2017), Expert Opinion on Therapeutic Patents. 28, 441-453.
  • [6] Ghosh, S., Mondal, S., Hajra, A. 2020. Direct catalytic functionalization of indazole derivatives, Advanced Synthesis and Catalysis. 362, 3768-3794.
  • [7] Schmidt, A., Beutler, A., Snovydovych, B. 2008. Recent advances in the chemistry of indazoles, European Journal of Organic Chemistry. 2008, 24, 4073-4095.
  • [8] Chevalier, A., Ouahrouch, A., Arnaud, A., Gallavardin, T., Franck, X. 2018. An optimized procedure for direct access to 1 H-indazole-3-carboxaldehyde derivatives by nitrosation of indoles, RSC Advances. 8, 13121-13128.
  • [9] Sathe, B. S., Jaychandran, E., Jagtap, V. A., Sreenivasa, G. M. 2011. Synthesis characterization and anti-inflammatory evaluation of new fluorobenzothiazole Schiff ’s bases. International Journal of Pharmaceutical Research and Development, vol. 3, no. 3, pp. 164–169.
  • [10] Chandramouli, C., Shivanand, M. R., Nayanbhai, T. B., Bheemachari, B., Udupi, R. H. 2012. Synthesis and biological screening of certain new triazole schiff bases and their derivatives bearing substituted benzothiazole moiety. Journal of Chemical and Pharmaceutical Research, 4, 2, 1151–1159.
  • [11] Ali, S. M. M., Abul Kalam Azad, M., Jesmin, M. et al. 2012. In vivo anticancer activity of Vanillin semicarbazones. Asian Pacific Journal of Tropical Biomedicine. 2, 6, 438–442.
  • [12] Liu, Y. X. 2005. Control of spermatogenesis in primate and prospect of male contraception. Archives of andrology, 51(2), 77-92.
  • [13] Lv, Z., Chu, Y., & Wang, Y. 2015. HIV protease inhibitors: a review of molecular selectivity and toxicity. HIV/AIDS-Research and palliative care, 95-104.
  • [14] Yousif, E., Majeed, A., Al-Sammarrae, K., Salih, N., Salimon, J., & Abdullah, B. 2017. Metal complexes of Schiff base: preparation, characterization and antibacterial activity. Arabian Journal of Chemistry, 10, S1639-S1644.
  • [15] Verma, M., Pandeya, S. N., Singh, K. N., & Stables, J. P. 2004. Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharmaceutica, 54(1), 49-56.
  • [16] Al Zoubi, W., Al‐Hamdani, A. A. S., & Kaseem, M. 2016. Synthesis and antioxidant activities of Schiff bases and their complexes: a review. Applied Organometallic Chemistry, 30(10), 810-817.
  • [17] Mphahlele, M. J., Magwaza, N. M., Gildenhuys, S., Setshedi, I. B. 2020. Synthesis, α-glucosidase inhibition and antioxidant activity of the 7-carbo-substituted 5-bromo-3- methylindazoles, Bioorganic Chemistry. 97, 103702.
  • [18] Rafique, K. M., Khan, S., Chigurupati, A., Wadood, A. U., Rehman, U., Salar, V., Venugopal, S., Shamim, M., Taha, S. 2020. Synthesis, in vitroα-amylase inhibitory, and radicals (DPPH and ABTS) scavenging potentials of new N-sulfonohydrazide substituted indazoles, Bioorganic Chemistry 94, 103410.
  • [19] Mai, H. X., Zhang, Y. W., Si, R., Yan, Z. G., Sun, L. D., You, L. P., & Yan, C. H. 2006. High-quality sodium rare- earth fluoride nanocrystals: controlled synthesis and optical properties. Journal of the American Chemical Society, 128(19), 6426-6436.
  • [20] Alpaslan, Y. B., Süleymanoğlu, N., Öztekin, E., Erşahin, F., Ağar, E., & Işık, Ş. 2010. Experimental and Semi-Empirical and DFT Calculational Studies on (E)-2-[(2, 4-Dichlorophenylimino) methyl]-p-cresol. Journal of Chemical Crystallography, 40, 950-956.
  • [21] Tanak, H., Erşahin, F., Köysal, Y., Ağar, E., Işık, Ş., & Yavuz, M. 2009. Theoretical modeling and experimental studies on Nn-Decyl-2-oxo-5-nitro-1-benzylidene-methylamine. Journal of molecular modeling, 15, 1281- 1290.
  • [22] Kurt, M., Sertbakan, T. R., & Özduran, M. 2008. An experimental and theoretical study of molecular structure and vibrational spectra of 3-and 4-pyridineboronic acid molecules by density functional theory calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 70(3), 664-673.
  • [23] Farrugia, L. J. 1999. WinGX suite for small-molecule single-crystal crystallography. journal of Applied Crystallography, 32(4), 837-838.
  • [24] Sheldrick, G. M. 2015. SHELXT–Integrated space-group and crystal-structure determination. Acta Crystallographica Section A: Foundations and Advances, 71(1), 3-8.
  • [25] Sheldrick, G. M. 2015. Crystal structure refinement with SHELXL. Acta Crystallographica Section C: Structural Chemistry, 71(1), 3-8.
  • [26] Farrugia, L. J. 1997. ORTEP-3 for Windows-a version of ORTEP-III with a Graphical User Interface (GUI). Applied Crystallography, 30(5), 565-565.
  • [27] Merrick, J. P., Moran, D. ve Radom, L. 2007. An evaluation of harmonic vibrational frequency scale factors. The Journal of Physical Chemistry A, 111(45): 11683-11700. doi: 10.1021/jp073974n
  • [28] Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, …, and Pople, J. A. 2004. Gaussian 03W, Revision E 01, Gaussian, Inc , Wallingford CT.
  • [29] Becke, A. D. 1993. Density functional thermochemistry. III. The role of exact exchange. The Journal of Chemical Physics, 98: 5648. doi: 10.1063/1.464913
  • [30] Lee, C., Yang, W. ve Parr, R. G. 1988, Development of the Colle-Salvetti correlation energy formula into a functional of the electron density, Physical Review B, 37 (2): 785-789. doi: 10.1103/PhysRevB.37.785
  • [31] Güzel, E., Macit, M., & Yavuz, M. 2023. (E)-2, 4-di-tert bütil-6-((4-florofenilimino) metil) fenol ve (E)-2, 4-di-tert-bütil-6-((3-iyodo-4-metilfenilimino) metil) fenol Bileşikleri için Moleküler Docking ve ADME Çalışmaları. Karadeniz Fen Bilimleri Dergisi, 13(3), 997-1011.
  • [32] Demircioğlu, Z., Kaştaş, G., Kaştaş, Ç. A., & Frank, R. 2019. Spectroscopic, XRD, Hirshfeld surface and DFT approach (chemical activity, ECT, NBO, FFA, NLO, MEP, NPA& MPA) of (E)-4-bromo-2-[(4-bromophenylimino) methyl]-6-ethoxyphenol. Journal of Molecular Structure, 1191, 129-137.
  • [33] Güzel, E., Macit, M., Ergüzeloğlu, E., & Yavuz, M. 2023. 3, 5-Di-Tert-Bütil-2-Hidroksibenzaldehit Bileşiğinin Kimyasal Aktivite ve Spektroskopik Çalışmaları. Journal of the Institute of Science and Technology, 13(1), 285-297.
  • [34] Kalecik, S., Güzel, E., Doğan, O. E., Ağar, E., & Yavuz, M. 2022. (E)-4-bromo-5-floro-2-(((4-(fenilamino) fenil) imino) metil) fenol Bileşiğinin Kimyasal Aktivite ve Spektroskopik Çalışmaları. Karadeniz Fen Bilimleri Dergisi, 12(2), 821-840.
  • [35] Hadjoudis, E., & Mavridis, I. M. 2004. Photochromism and thermochromism of Schiff bases in the solid state: structural aspects. Chemical Society Reviews, 33(9), 579-588.
  • [36] Kaynar, N. K., Yavuz, M., Tanak, H., Şahin, S., Büyükgüngör, O., & Ağar, E. 2018. Crystal Structure of 2-((E)-(5-Bromo-2-hydroxybenzylidene) hydrazono)-1, 2-diphenylethanone. Crystallography Reports, 63, 375-378.
  • [37] Demircioğlu, Z., Albayrak, Ç., & Büyükgüngör, O. 2014. Theoretical and experimental investigation of (E)-2-([3, 4-dimethylphenyl) imino] methyl)-3-methoxyphenol: Enol–keto tautomerism, spectroscopic properties, NLO, NBO and NPA analysis. Journal of Molecular Structure, 1065, 210-222.
  • [38] Ulu, Ö. D., Serin, S., Özdemir, N., & Özdemir, İ. 2024. Synthesis, Crystal Structure, and DFT Studies of NHC Mediated Pd-PEPPSI Complex: Application for Suzuki Reaction. Journal of Molecular Structure, 139479.
  • [39] Kucuk, C., Celik, S., Yurdakul, S., Özdemir, N., & Bülbül, H. 2024. Characterization of the synthesized diaqua-bis (indazole-κN2) bis (nitrato-κO) zinc (II) complex and DFT calculations. Journal of Molecular Structure, 1304, 137666.

Structure Characterization of Schiff-Based Indazole Compound and Investigation with Theoretical Calculations

Year 2024, , 472 - 482, 23.12.2024
https://doi.org/10.19113/sdufenbed.1523523

Abstract

E)-4-Methoxy-2-(((4-methoxy-1H-indazol-3-yl)imino)methyl)phenol compound was structurally characterized using IR, UV-Vis, 13C-NMR / 1H-NMR and X-ray diffraction methods and it was determined that the compound structure was in the enol-imine form. Hirshfeld surface analysis was used to visualize the 3-dimensional surface properties of the molecular structure. The 6-311G(d,p) basis set of Density Functional Theory was used to determine the theoretical properties of the molecular structure. The UV-Vis spectra of the title compound were prepared in DMSO at a concentration of 5x10-5 M. 13C-NMR and 1H-NMR characterization analyses were given comparatively experimentally and theoretically. Detailed studies were made on the electrophilic nature, nucleophilic nature and chemical activities of the molecular structure with the help of theoretical calculations. As a result of these studies, we reached information on frontier molecular orbitals, hardness, softness, mulliken population analysis charges, MEP and contour surfaces. In addition, we combined our molecular structure theoretically with the basic building blocks of DNA, adenine, cytosine, guanine and thymine bases and made calculations. As a result of these calculations, ECT (electrophilic based charge transfer) method and DN (charge transfer) were used to investigate the charge transfer and electrophilic and nucleophilic nature of the molecular structure.

Project Number

PYO.FEN.1904.22.026

References

  • [1] Schiff, H. 1864. Mittheilungen aus dem Universitatslaboratorium in ¨ Pisa: eine neue reihe organischer Basen. Justus Liebigs Annalen der Chemie, 131, 1, 118–119.
  • [2] Dominiak, P. M., Grech, E., Barr, G., Teat, S., Mallinson, P., Wozniak, K., 2003. Neutral and ionic hydrogen bonding in Schiff bases. Chem. Eur. J., 9(4), 963- 970.
  • [3] Güzel, E., Macit, M., Ergüzeloğlu, E., Kalecik, S., Keleşoğlu, Z., & Yavuz, M. 2023. Two new Schiff bases of (E)-2, 4-di-tert-butyl-6-((4-fluorophenylimino) methyl) phenol (I) and (E)-2, 4-di-tert-butyl-6-((3-iodo-4-methylphenylimino) methyl) phenol (II): structural, spectroscopic and quantum chemical calculations. Molecular Crystals and Liquid Crystals, 763(1), 96-113.
  • [4] Fischer, E. 1884. Phenylhydrazin als reagens auf aldehyde und ketone. Berichte der deutschen chmemischen ,Gesellschaft.
  • [5] Denya, S.F., Malan, J. 2018. Joubert, Indazole derivatives and their therapeutic applications: a patent review (2013-2017), Expert Opinion on Therapeutic Patents. 28, 441-453.
  • [6] Ghosh, S., Mondal, S., Hajra, A. 2020. Direct catalytic functionalization of indazole derivatives, Advanced Synthesis and Catalysis. 362, 3768-3794.
  • [7] Schmidt, A., Beutler, A., Snovydovych, B. 2008. Recent advances in the chemistry of indazoles, European Journal of Organic Chemistry. 2008, 24, 4073-4095.
  • [8] Chevalier, A., Ouahrouch, A., Arnaud, A., Gallavardin, T., Franck, X. 2018. An optimized procedure for direct access to 1 H-indazole-3-carboxaldehyde derivatives by nitrosation of indoles, RSC Advances. 8, 13121-13128.
  • [9] Sathe, B. S., Jaychandran, E., Jagtap, V. A., Sreenivasa, G. M. 2011. Synthesis characterization and anti-inflammatory evaluation of new fluorobenzothiazole Schiff ’s bases. International Journal of Pharmaceutical Research and Development, vol. 3, no. 3, pp. 164–169.
  • [10] Chandramouli, C., Shivanand, M. R., Nayanbhai, T. B., Bheemachari, B., Udupi, R. H. 2012. Synthesis and biological screening of certain new triazole schiff bases and their derivatives bearing substituted benzothiazole moiety. Journal of Chemical and Pharmaceutical Research, 4, 2, 1151–1159.
  • [11] Ali, S. M. M., Abul Kalam Azad, M., Jesmin, M. et al. 2012. In vivo anticancer activity of Vanillin semicarbazones. Asian Pacific Journal of Tropical Biomedicine. 2, 6, 438–442.
  • [12] Liu, Y. X. 2005. Control of spermatogenesis in primate and prospect of male contraception. Archives of andrology, 51(2), 77-92.
  • [13] Lv, Z., Chu, Y., & Wang, Y. 2015. HIV protease inhibitors: a review of molecular selectivity and toxicity. HIV/AIDS-Research and palliative care, 95-104.
  • [14] Yousif, E., Majeed, A., Al-Sammarrae, K., Salih, N., Salimon, J., & Abdullah, B. 2017. Metal complexes of Schiff base: preparation, characterization and antibacterial activity. Arabian Journal of Chemistry, 10, S1639-S1644.
  • [15] Verma, M., Pandeya, S. N., Singh, K. N., & Stables, J. P. 2004. Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharmaceutica, 54(1), 49-56.
  • [16] Al Zoubi, W., Al‐Hamdani, A. A. S., & Kaseem, M. 2016. Synthesis and antioxidant activities of Schiff bases and their complexes: a review. Applied Organometallic Chemistry, 30(10), 810-817.
  • [17] Mphahlele, M. J., Magwaza, N. M., Gildenhuys, S., Setshedi, I. B. 2020. Synthesis, α-glucosidase inhibition and antioxidant activity of the 7-carbo-substituted 5-bromo-3- methylindazoles, Bioorganic Chemistry. 97, 103702.
  • [18] Rafique, K. M., Khan, S., Chigurupati, A., Wadood, A. U., Rehman, U., Salar, V., Venugopal, S., Shamim, M., Taha, S. 2020. Synthesis, in vitroα-amylase inhibitory, and radicals (DPPH and ABTS) scavenging potentials of new N-sulfonohydrazide substituted indazoles, Bioorganic Chemistry 94, 103410.
  • [19] Mai, H. X., Zhang, Y. W., Si, R., Yan, Z. G., Sun, L. D., You, L. P., & Yan, C. H. 2006. High-quality sodium rare- earth fluoride nanocrystals: controlled synthesis and optical properties. Journal of the American Chemical Society, 128(19), 6426-6436.
  • [20] Alpaslan, Y. B., Süleymanoğlu, N., Öztekin, E., Erşahin, F., Ağar, E., & Işık, Ş. 2010. Experimental and Semi-Empirical and DFT Calculational Studies on (E)-2-[(2, 4-Dichlorophenylimino) methyl]-p-cresol. Journal of Chemical Crystallography, 40, 950-956.
  • [21] Tanak, H., Erşahin, F., Köysal, Y., Ağar, E., Işık, Ş., & Yavuz, M. 2009. Theoretical modeling and experimental studies on Nn-Decyl-2-oxo-5-nitro-1-benzylidene-methylamine. Journal of molecular modeling, 15, 1281- 1290.
  • [22] Kurt, M., Sertbakan, T. R., & Özduran, M. 2008. An experimental and theoretical study of molecular structure and vibrational spectra of 3-and 4-pyridineboronic acid molecules by density functional theory calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 70(3), 664-673.
  • [23] Farrugia, L. J. 1999. WinGX suite for small-molecule single-crystal crystallography. journal of Applied Crystallography, 32(4), 837-838.
  • [24] Sheldrick, G. M. 2015. SHELXT–Integrated space-group and crystal-structure determination. Acta Crystallographica Section A: Foundations and Advances, 71(1), 3-8.
  • [25] Sheldrick, G. M. 2015. Crystal structure refinement with SHELXL. Acta Crystallographica Section C: Structural Chemistry, 71(1), 3-8.
  • [26] Farrugia, L. J. 1997. ORTEP-3 for Windows-a version of ORTEP-III with a Graphical User Interface (GUI). Applied Crystallography, 30(5), 565-565.
  • [27] Merrick, J. P., Moran, D. ve Radom, L. 2007. An evaluation of harmonic vibrational frequency scale factors. The Journal of Physical Chemistry A, 111(45): 11683-11700. doi: 10.1021/jp073974n
  • [28] Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, …, and Pople, J. A. 2004. Gaussian 03W, Revision E 01, Gaussian, Inc , Wallingford CT.
  • [29] Becke, A. D. 1993. Density functional thermochemistry. III. The role of exact exchange. The Journal of Chemical Physics, 98: 5648. doi: 10.1063/1.464913
  • [30] Lee, C., Yang, W. ve Parr, R. G. 1988, Development of the Colle-Salvetti correlation energy formula into a functional of the electron density, Physical Review B, 37 (2): 785-789. doi: 10.1103/PhysRevB.37.785
  • [31] Güzel, E., Macit, M., & Yavuz, M. 2023. (E)-2, 4-di-tert bütil-6-((4-florofenilimino) metil) fenol ve (E)-2, 4-di-tert-bütil-6-((3-iyodo-4-metilfenilimino) metil) fenol Bileşikleri için Moleküler Docking ve ADME Çalışmaları. Karadeniz Fen Bilimleri Dergisi, 13(3), 997-1011.
  • [32] Demircioğlu, Z., Kaştaş, G., Kaştaş, Ç. A., & Frank, R. 2019. Spectroscopic, XRD, Hirshfeld surface and DFT approach (chemical activity, ECT, NBO, FFA, NLO, MEP, NPA& MPA) of (E)-4-bromo-2-[(4-bromophenylimino) methyl]-6-ethoxyphenol. Journal of Molecular Structure, 1191, 129-137.
  • [33] Güzel, E., Macit, M., Ergüzeloğlu, E., & Yavuz, M. 2023. 3, 5-Di-Tert-Bütil-2-Hidroksibenzaldehit Bileşiğinin Kimyasal Aktivite ve Spektroskopik Çalışmaları. Journal of the Institute of Science and Technology, 13(1), 285-297.
  • [34] Kalecik, S., Güzel, E., Doğan, O. E., Ağar, E., & Yavuz, M. 2022. (E)-4-bromo-5-floro-2-(((4-(fenilamino) fenil) imino) metil) fenol Bileşiğinin Kimyasal Aktivite ve Spektroskopik Çalışmaları. Karadeniz Fen Bilimleri Dergisi, 12(2), 821-840.
  • [35] Hadjoudis, E., & Mavridis, I. M. 2004. Photochromism and thermochromism of Schiff bases in the solid state: structural aspects. Chemical Society Reviews, 33(9), 579-588.
  • [36] Kaynar, N. K., Yavuz, M., Tanak, H., Şahin, S., Büyükgüngör, O., & Ağar, E. 2018. Crystal Structure of 2-((E)-(5-Bromo-2-hydroxybenzylidene) hydrazono)-1, 2-diphenylethanone. Crystallography Reports, 63, 375-378.
  • [37] Demircioğlu, Z., Albayrak, Ç., & Büyükgüngör, O. 2014. Theoretical and experimental investigation of (E)-2-([3, 4-dimethylphenyl) imino] methyl)-3-methoxyphenol: Enol–keto tautomerism, spectroscopic properties, NLO, NBO and NPA analysis. Journal of Molecular Structure, 1065, 210-222.
  • [38] Ulu, Ö. D., Serin, S., Özdemir, N., & Özdemir, İ. 2024. Synthesis, Crystal Structure, and DFT Studies of NHC Mediated Pd-PEPPSI Complex: Application for Suzuki Reaction. Journal of Molecular Structure, 139479.
  • [39] Kucuk, C., Celik, S., Yurdakul, S., Özdemir, N., & Bülbül, H. 2024. Characterization of the synthesized diaqua-bis (indazole-κN2) bis (nitrato-κO) zinc (II) complex and DFT calculations. Journal of Molecular Structure, 1304, 137666.
There are 39 citations in total.

Details

Primary Language Turkish
Subjects Atomic and Molecular Physics, Condensed Matter Modelling and Density Functional Theory
Journal Section Articles
Authors

Enis Güzel 0000-0001-8068-2934

Aliye Ertürk 0000-0003-0831-7056

Metin Yavuz 0000-0002-1262-9135

Project Number PYO.FEN.1904.22.026
Publication Date December 23, 2024
Submission Date July 28, 2024
Acceptance Date August 29, 2024
Published in Issue Year 2024

Cite

APA Güzel, E., Ertürk, A., & Yavuz, M. (2024). Schiff Bazlı İndazol Bileşiğinin Yapı Karakterizasyonu ve Kuramsal Hesaplamalarla İncelenmesi. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 28(3), 472-482. https://doi.org/10.19113/sdufenbed.1523523
AMA Güzel E, Ertürk A, Yavuz M. Schiff Bazlı İndazol Bileşiğinin Yapı Karakterizasyonu ve Kuramsal Hesaplamalarla İncelenmesi. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. December 2024;28(3):472-482. doi:10.19113/sdufenbed.1523523
Chicago Güzel, Enis, Aliye Ertürk, and Metin Yavuz. “Schiff Bazlı İndazol Bileşiğinin Yapı Karakterizasyonu Ve Kuramsal Hesaplamalarla İncelenmesi”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 28, no. 3 (December 2024): 472-82. https://doi.org/10.19113/sdufenbed.1523523.
EndNote Güzel E, Ertürk A, Yavuz M (December 1, 2024) Schiff Bazlı İndazol Bileşiğinin Yapı Karakterizasyonu ve Kuramsal Hesaplamalarla İncelenmesi. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 28 3 472–482.
IEEE E. Güzel, A. Ertürk, and M. Yavuz, “Schiff Bazlı İndazol Bileşiğinin Yapı Karakterizasyonu ve Kuramsal Hesaplamalarla İncelenmesi”, Süleyman Demirel Üniv. Fen Bilim. Enst. Derg., vol. 28, no. 3, pp. 472–482, 2024, doi: 10.19113/sdufenbed.1523523.
ISNAD Güzel, Enis et al. “Schiff Bazlı İndazol Bileşiğinin Yapı Karakterizasyonu Ve Kuramsal Hesaplamalarla İncelenmesi”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 28/3 (December 2024), 472-482. https://doi.org/10.19113/sdufenbed.1523523.
JAMA Güzel E, Ertürk A, Yavuz M. Schiff Bazlı İndazol Bileşiğinin Yapı Karakterizasyonu ve Kuramsal Hesaplamalarla İncelenmesi. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. 2024;28:472–482.
MLA Güzel, Enis et al. “Schiff Bazlı İndazol Bileşiğinin Yapı Karakterizasyonu Ve Kuramsal Hesaplamalarla İncelenmesi”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, vol. 28, no. 3, 2024, pp. 472-8, doi:10.19113/sdufenbed.1523523.
Vancouver Güzel E, Ertürk A, Yavuz M. Schiff Bazlı İndazol Bileşiğinin Yapı Karakterizasyonu ve Kuramsal Hesaplamalarla İncelenmesi. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. 2024;28(3):472-8.

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