Yıl 2018, Cilt 14, Sayı 3, Sayfalar 261 - 269 2018-09-30

A Computational Study on the Nucleophilic Substitution Reaction between 2-Bromoacetophenone and Azole Derivatives

Taner Erdoğan [1]

40 53

In this study, it was aimed to investigate the reaction of 2-bromoacetophenone with various azole derivatives, such as imidazole, benzimidazole, 1,2,4-triazole and benzotriazole computationally. For this purpose, some Density Functional Theory (DFT) calculations have been carried out on the reactants and products at B3LYP (Becke, three-parameter, Lee-Yang-Parr) level of theory using various basis sets, including 6-31G(d), 6-31G(d,p), 6-311G(d,p) and 6-311+G(2d,p). Geometry optimizations, Single Point Energy (SPE) calculations, frequency analysis, frontier molecular orbital calculations, molecular electrostatic potential (MEP) map calculations, and determination of global reactivity descriptors have been carried out at the same levels of theory. In NMR calculations, both Continuous Set of Gauge Transformations (CSGT) and Gauge-Independent Atomic Orbital (GIAO) methods have been used and computationally obtained data have been compared with the experimental data.
Computational chemistry, DFT, 2-bromoacetophenone, azole
  • 1. Porretta, G.C, Fioravanti, R, Biava, M, Cirilli, R, Simonetti, N, Villa, A, Bello, U, Faccendini, P, Tita, B, research on antibacterial and antifungal agents.10. synthesis and antimicrobial activities of 1-phenyl-2-(1H-azol-1-yl) ethane derivatives - anticonvulsant activity of 1-(4-methylphenyl)-2-(1H-imidazol-1-yl) ethanol, European Journal of Medicinal Chemistry, 1993, 28, 749-760.
  • 2. Guven, O.O, Erdogan, T, Goker, H, Yildiz, S, Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers, Bioorganic & Medicinal Chemistry Letters, 2007, 17, 2233-2236.
  • 3. Rad, M.N.S, Khalafi-Nezhad, A, Behrouz, S, Design and Synthesis of Some Novel Oxiconazole-Like Carboacyclic Nucleoside Analogues, as Potential Chemotherapeutic Agents, Helvetica Chimica Acta, 2009, 92, 1760-1774.
  • 4. Dogan, I.S, Sarac, S, Sari, S, Kart, D, Gokhan, S.E, Vural, I, Dalkara, S, New azole derivatives showing antimicrobial effects and their mechanism of antifungal activity by molecular modeling studies, European Journal of Medicinal Chemistry, 2017, 130, 124-138.
  • 5. Guven, O.O, Erdogan, T, Coles, S.J, Hokelek, T, 2-(1H-benzimidazol-1-yl)-1-phenylethanone, Acta Crystallogr. Sect. E.-Struct Rep. Online, 2008, 64, O1358-U2746.
  • 6. Guven, O.O, Tahtaci, H, Coles, S.J, Hokelek, T, 1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanone, Acta Crystallogr. Sect. E.-Struct Rep. Online, 2008, 64, O1604-U3253.
  • 7. Oh, K, Nakai, K, Yamada, K, Yoshizawa, Y, Synthesis of novel triazole derivatives as potent inhibitor of allene oxide synthase (CYP74A), a key enzyme in jasmonic acid biosynthesis, Journal of Pesticide Science, 2012, 37, 80-84.
  • 8. Chen, S.Q, Liu, F.M, Synthesis and Crystal Structure of Compound 1-Phenyl-2-(1H-1,2,4-triazolo-yl)-3-phenyl-propen-1-one and 1-Diphenyl-3-(1,2,4-triazolo-yl)-1H,4H-1,5-benzothiazepine, Journal of Chemical Crystallography, 2011, 41, 485-490.
  • 9. Katritzky, A.R, Wrobel, L, Savage, G.P, Deyrupdrewniak, M, The formation of ketones by a reaction equivalent to R-+R'COCH2+- R'COCH2R, Australian Journal of Chemistry, 1990, 43, 133-139.
  • 10. Yousefi, R, Khalafi-Nezhad, A, Rad, M.N.S, Behrouz, S, Panahi, F, Esmaili, M, Ghaffari, S.M, Niazi, A, Moosavi-Movahedi, A.A, Structure-cytotoxicity relationship of a novel series of miconazole-like compounds, Medical Chemistry Research, 2012, 21, 1921-1928.
  • 11. Frisch, M.J, Trucks, G.W, Schlegel, H.B, Scuseria, G.E, Robb, M.A, Cheeseman, J.R, Scalmani, G, Barone, V, Mennucci, B, Petersson, G.A, Nakatsuji, H, Caricato, M, Li, X, Hratchian, H.P, Izmaylov, A.F, Bloino, J, Zheng, G, Sonnenberg, J.L, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Vreven, T, Montgomery, J, J. A. , Peralta, JE, Ogliaro, F, Bearpark, M, Heyd, J.J, Brothers, E, Kudin, K.N, Staroverov, V.N, Keith, T, Kobayashi, R, Normand, J, Raghavachari, K, Rendell, A, Burant, J.C, Iyengar, S.S, Tomasi, J, Cossi, M, Rega, N, Millam, J.M, Klene, M, Knox, JE, Cross, J.B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R.E, Yazyev, O, Austin, A.J, Cammi, R, Pomelli, C, Ochterski, J.W, Martin, R.L, Morokuma, K, Zakrzewski, V.G, Voth, G.A, Salvador, P, Dannenberg, J.J, Dapprich, S, Daniels, A.D, Farkas, O, Foresman, J.B, Ortiz, J.V, Cioslowski, J, Fox, DJ, Gaussian 09. 2013, Gaussian Inc.: Wallingford CT.
  • 12. Hanwell, M.D, Curtis, D.E, Lonie, D.C, Vandermeersch, T, Zurek, E, Hutchison, G.R, Avogadro: An advanced semantic chemical editor, visualization, and analysis platform, Journal of Cheminformatics, 2012, 4, 17.
  • 13. Dennington, R, Keith, T, Millam, J, GaussView, Version 5. 2009, Semichem Inc.: Shawnee Mission, KS.
  • 14. Prasad, P.K, Reddi, R.N, Sudalai, A, Regioselective Oxo-Amination of Alkenes and Enol Ethers with N-Bromosuccinimide–Dimethyl Sulfoxide Combination: A Facile Synthesis of α-Amino-Ketones and Esters, Organic Letters, 2016, 18, 500-503.
  • 15. Chattaraj, P.K, Sarkar, U, Roy, D.R, Electrophilicity index, Chemistry Reviews, 2006, 106, 2065-2091.
  • 16. Mulliken, R.S, A New Electroaffinity Scale; Together with Data on Valence States and on Valence Ionization Potentials and Electron Affinities, Journal of Chemistry. Physics, 1934, 2, 782.
  • 17. Parr, R.G, Pearson, R.G, Absolute Hardness-Companion Parameter to Absolute Electronegativity, Journal of the American Chemical Society, 1983, 105, 7512-7516.
  • 18. Parr, R.G, Von Szentpaly, L, Liu, S.B, Electrophilicity index, Journal of the American Chemical Society, 1999, 121, 1922-1924.
  • 19. Pearson, R.G, Hard and Soft Acids and Bases HSAB.1.Fundamental Principles, Journal of Chemistry Education, 1968, 45, 581-587.
  • 20. Pearson, R.G, Maximum chemical and physical hardness, Journal of Chemistry Education, 1999, 76, 267-275.
Birincil Dil en
Konular Mühendislik
Dergi Bölümü Makaleler
Yazarlar

Yazar: Taner Erdoğan (Sorumlu Yazar)
Kurum: Kocaeli University, Kocaeli Vocational School, Department of Chemistry and Chemical Processing Technologies, Kocaeli, Turkey
Ülke: Turkey


Bibtex @araştırma makalesi { cbayarfbe415975, journal = {Celal Bayar Üniversitesi Fen Bilimleri Dergisi}, issn = {1305-130X}, eissn = {1305-1385}, address = {Celal Bayar Üniversitesi}, year = {2018}, volume = {14}, pages = {261 - 269}, doi = {10.18466/cbayarfbe.415975}, title = {A Computational Study on the Nucleophilic Substitution Reaction between 2-Bromoacetophenone and Azole Derivatives}, key = {cite}, author = {Erdoğan, Taner} }
APA Erdoğan, T . (2018). A Computational Study on the Nucleophilic Substitution Reaction between 2-Bromoacetophenone and Azole Derivatives. Celal Bayar Üniversitesi Fen Bilimleri Dergisi, 14 (3), 261-269. DOI: 10.18466/cbayarfbe.415975
MLA Erdoğan, T . "A Computational Study on the Nucleophilic Substitution Reaction between 2-Bromoacetophenone and Azole Derivatives". Celal Bayar Üniversitesi Fen Bilimleri Dergisi 14 (2018): 261-269 <http://dergipark.gov.tr/cbayarfbe/issue/39486/415975>
Chicago Erdoğan, T . "A Computational Study on the Nucleophilic Substitution Reaction between 2-Bromoacetophenone and Azole Derivatives". Celal Bayar Üniversitesi Fen Bilimleri Dergisi 14 (2018): 261-269
RIS TY - JOUR T1 - A Computational Study on the Nucleophilic Substitution Reaction between 2-Bromoacetophenone and Azole Derivatives AU - Taner Erdoğan Y1 - 2018 PY - 2018 N1 - doi: 10.18466/cbayarfbe.415975 DO - 10.18466/cbayarfbe.415975 T2 - Celal Bayar Üniversitesi Fen Bilimleri Dergisi JF - Journal JO - JOR SP - 261 EP - 269 VL - 14 IS - 3 SN - 1305-130X-1305-1385 M3 - doi: 10.18466/cbayarfbe.415975 UR - http://dx.doi.org/10.18466/cbayarfbe.415975 Y2 - 2018 ER -
EndNote %0 Celal Bayar Üniversitesi Fen Bilimleri Dergisi A Computational Study on the Nucleophilic Substitution Reaction between 2-Bromoacetophenone and Azole Derivatives %A Taner Erdoğan %T A Computational Study on the Nucleophilic Substitution Reaction between 2-Bromoacetophenone and Azole Derivatives %D 2018 %J Celal Bayar Üniversitesi Fen Bilimleri Dergisi %P 1305-130X-1305-1385 %V 14 %N 3 %R doi: 10.18466/cbayarfbe.415975 %U 10.18466/cbayarfbe.415975
ISNAD Erdoğan, Taner . "A Computational Study on the Nucleophilic Substitution Reaction between 2-Bromoacetophenone and Azole Derivatives". Celal Bayar Üniversitesi Fen Bilimleri Dergisi 14 / 3 (Eylül 2018): 261-269. http://dx.doi.org/10.18466/cbayarfbe.415975