DFT Yöntemi Kullanılarak 1,3-Bis- {(2-Aminobenzoil) Amino} Propanın Teorik Hesaplamaları Ve Bu Değerlerin Literatürdeki Deneysel Değerler İle Karşılaştırılması

Bu çalışmada, 1,3-Bis-{(2-aminobenzoil)amino}propan (1) molekülünün geometrik özellikleri (bağ uzunluğu, bağ açısı ve burulma açısı), elektronik özellikleri (elektronegatiflik, kimyasal potansiyel), en yüksek dolu moleküler orbital (HOMO) ve en düşük boş moleküler orbitallerin (LUMO) enerjileri ve Mulliken atomik yükleri Gaussian 09 programı kullanılarak incelenmiştir. Yoğunluk fonksiyonel metodu (DFT/B3LYP) ile 6-311++G(2d,p) baz seti kullanılarak molekül (1)’in yapısal ve spektroskopik değerleri hesaplanarak literatürdeki deneysel verilerle karşılaştırılmıştır.

Anahtar Kelimeler:

İsatoik anhidrid, Gaussian 09, 6-311++G(2d.p), DFT/B3LYP

Theoretical Calculations Of 1,3-Bis- {(2-Aminobenzoyl) Amino} Propane Using DFT Method And Comparison Of These Values With Experimental Values İn Literatüre

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[1] A. F. Hegarty, E. P. Ahern, L. N. Frostb and C. N. Hegartyb, “Reactions of lsatoic Anhydride as a Masked Isocyanate with Oxygen and Nitrogen Nucleophiles-Kinetics and Mechanism,” J. Chem. Soc. Perkın Trans. 2, pp. 1935-1941, 1990.
[2] Y. N. Mabkhot, A. M. Al-Majid, A. Barakat, S. S. Al-Showiman, M. S. Al-Har, S. Radi, M. M. Naseer and T. B. Hadda, “Synthesis and Biological Evaluation of 2-Aminobenzamide Derivatives as Antimicrobial Agents: Opening/Closing Pharmacophore Site,” Int. J. Mol. Sci., vol. 15, pp. 5115-5127, 2014.
[3] S. M. Ebrahimi, M. Mahdavi, S. Emami, M. Saeedi, M. Asadi, L. Firoozpour, M. Khoobi, K. Divsalar, A. Shafiee, and A. Foroumadi, “Green and Catalyst-Free One-Pot Synthesis of Anthranilamide Schiff Bases: An Approach Toward Sirtinol,” Synth. Commun., vol. 44, pp. 665–673, 2014.
[4] I. Khan, A. Ibrar, N. Abbas, A. Saeed, “Recent advances in the structural library of functionalized quinazoline and quinazolinone scaffolds: Synthetic approaches and multifarious applications,” Eur. J. Med. Chem., vol. 76, pp. 193-244, 2014.
[5] N. Menges, Ö. Sarı, Y. Abdullayev, S. S. Erdem, and M. Balcı, “Design and Synthesis of Pyrrolotriazepine Derivatives: An Experimental and Computational Study,” J. Org. Chem., vol. 78, pp. 5184−5195, 2013.
[6] M. Zora, İ. Özkan, “Substituent effects on the transannular ring closure of 2,4-cylooctadienones to 5,5-fused ring systems: AM1 study,” J. Mol. Struct.(Theochem), vol. 583, pp. 233-239, 2002.
[7] S. D. Kanmazalp, “Investigation of Theoretical Calculations of 2-(1-Phenylethylideneamino) Guanidine Compound: NBO, NLO, HOMO-LUMO and MEP Analysis by DFT Method,” Karaelmas Fen ve Müh. Derg., vol. 7, no. 2, pp. 491-496, 2017.
[8] P. I. Nagy, “The syn–anti equilibrium for the ACOOH group reinvestigated. Theoretical conformation analysis for acetic acid in the gas phase and in solution,” Comput. Theor. Chem., vol. 1022, pp. 59–69, 2013.
[9] M. Ateş, H. Kolancılar, S. Çalışkan and D. Çınar, “The electropolymerization of N,N0-(propane-1,3-diyl)bis(2-aminobenzamide) characterization, and capacitor study,” High Perform. Polym., vol. 30, no. 1, pp. 82–93, 2018.
[10] N. Hunter and K. Vaughan, “Synthesis and Characterization of a Series of 1,x-bis-(4-Oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)alkanes,” J. Heterocyclic Chem., c. 43, ss. 731-738, 2006.
[11] S. J. Swamy, K. Suresh, P. Someshwar, and D. Nagaraju, “Synthesis of Novel Schiff’s Bases Containing Pyridine Rings,” Synth. Commun., voll. 34, no. 10, pp. 1847–1853, 2004.
[12] İ. Şen, “Bazı Aromatik Amit Bileşiklerinin ve Metal Komplekslerinin Sentezi ve Hesapsal Yöntemlerle İncelenmesi,” Doktora Tezi, Kimya Bölümü, Balıkesir Üniversitesi, Balıkesir, Türkiye, 2011.
[13] A. D. Becke, “Density‐functional thermochemistry. III. The role of exact Exchange,” J. Chem. Phys., vol. 98, pp. 5648-5652, 1993.
[14] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr. J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, T. Keith, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Rev D.1, Gaussian, Inc., Wallingford CT, 2013.
[15] A. D. Becke, “Density‐functional thermochemistry. III. The role of exact Exchange,” The Journal of Chemical Physics,” vol. 98, pp. 5648-5652, 1993.
[16] C. Lee, W. Yang, R. G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Phys. Rev. B, vol. 37, pp. 785–789, 1988.
[17] G. Uluçam, S. E. Okan, Ş. Aktaş and G. P. Ögretmen, “Characterization of dinaphthosulfoxide molecule,” J. Mol. Struct., vol. 1102, pp. 146-152, 2015.
[18] J. S. Sreedasyam, J. Sunkari, S. Kundha, R. R. Gundapaneni, “N,N΄-(Propane-1,3-diyl)bis(2-aminobenzamide),” Acta Cryst. E69, 673, 2013.
[19] S. Altürk, “1,3-Tiyazolidin-2,4-Dikarboksilat-Mn(II) Kompleksinin 1,10-Fenantrolin ile Sentezi, Spektroskopik Karakterizasyonu ve DFT Metoduyla İncelenmesi,” Yüksek Lisans Tezi, Kimya Bölümü, Sakarya Üniversitesi, Sakarya, Türkiye, 2015.
[20] S. Altürk, D. Avcı, Ö. Tamer, Y. Atalay, O. Şahin, “A cobalt (II) complex with 6-methylpicolinate: Synthesis, characterization, second- and third-order nonlinear optical properties, and DFT calculations,” J. Phys. Chem. Solids, vol. 98, pp. 71–80, 2016.
[21] H. N. Mishra, S. R. Kumar, N. Vijay, C. Satish, S. Alok Kumar, S. V. Kuamr, P. Onkar and S. Leena, “Electronic structure, Non-inear properties and Vibrational analysis of ortho, meta and para -Hydroxybenzaldehyde by Density Functional Theory,” Res. J. Rec. Sci., vol. 2, pp. 150-157, 2013.
[22] Ö. Tamer, D. Avcı, Y. Atalay, “Synthesis, X-Ray Crystal Structure, Photophysical Characterization and Nonlinear Optical Properties of The Unique Manganese Complex with Picolinate and 1,10 Phenantroline: Toward The Designing of New High NLO Response Crystal,” J. Phys. Chem. Solids, vol. 99, pp. 124–133, 2016.
[23] R. G. Pearson, “Absolute electronegativity and hardness correlated with molecular orbital theory,” Proc. Natl. Acad. Sci. USA, c. 83, ss. 8440-8441, 1986.
[24] A. Vela and J. L. Gizquez, A Relationship between the Static Dipole Polarizability, the Global Softness, and the Fukui Function, J. Am. Chem. Soc., vol. 112, pp. 1490-1492, 1990.
[25] S. Altürk, Ö. Tamer, D. Avcı, Y. Atalay, “Synthesis, Spectroscopic Characterization, Second and Third-Order Nonlinear Optical Properties, and DFT Calculations of a Novel Mn(II) Complex,” J. Organometal. Chem., vol. 797, pp. 110-119, 2015.
[26] S. Altürk, D. Avcı, Ö. Tamer, Y. Atalay, “1H-pyrazole-3-carboxylic acid: Experimental and Computational Study,” J. Mol. Struct., vol. 1164, pp. 28-36, 2018.