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2- (azepan-1-il (naftalen-1-il) metil)fenol Bileşiğinin Sentezi ve Kuantum Kimyasal Hesaplamaları

Yıl 2020, Sayı: 18, 574 - 582, 15.04.2020
https://doi.org/10.31590/ejosat.682673

Öz

2- (azepan-1-il (naftalen-1-il) metil) fenol bileşiği bir alkilaminofenol bileşiğidir ve petasis reaksiyonu ile deneysel olarak sentezlenmiştir. Bu çalışmada yapısal analizler FT-IR, NMR, UV-Vis spektroskopisi ile yapılmıştır. Deneysel verilerin, teorik veriler ile desteklenmesi için bileşiğe ait birçok fizikokimyasal parametre 6-311G ++ (d,p) seti ve DFT (B3LYP) yöntemi ile araştırılmıştır. Bileşiğin elektronik ve yapısal özellikleri (bağ uzunlukları, bağ açıları ve dihedral açılar), HOMO (en yüksek dolu moleküler orbital) ve LUMO (en düşük boş moleküler orbital) enerjileri, elektrostatik potansiyel (MEP), titreşim frekansları, Mulliken atom yükleri, uyarım enerjileri ve osilatör kuvvetleri gibi özellikleri hesaplanmıştır. Teorik değerler ve deneysel değerler uyumlu olduğu görülmüş, mevcut sapmaların kaynağı ve nedenleri hakkında bilgi verilmiştir.

Destekleyen Kurum

Bursa Uludağ Üniversitesi Bilimsel Araştırma Projeleri Birimi

Proje Numarası

KUAP(F)-2016/5

Teşekkür

Bursa Uludağ Üniversitesi Bilimsel Araştırma Projeleri Birimi

Kaynakça

  • Becke, A. D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38(6), 3098–3100.
  • Beisel, T., & Manolikakes, G. (2015). Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Substituted Amines. Organic Letters, 17(12), 3162–3165.
  • Borisov, Y. A., & Akhrem, I. S. (2019). DFT B3LYP/6-311+G* calculation study of a new nonclassical mechanism of electrophilic functionalization of aromatic C–H bond via aryl cation formation. Mendeleev Communications, 29(3), 343–345.
  • Candeias, N. R., Montalbano, F., Cal, P. M. S. D., & Gois, P. M. P. (2010). Boronic acids and esters in the petasis-borono mannich multicomponent reaction. Chemical Reviews, 110(10), 6169–6193.
  • Chouguiat, L., Boulcina, R., Carboni, B., Demonceau, A., & Debache, A. (2014). A new and efficient one-pot synthesis of 2-hydroxy-1,4-dihydrobenzoxazines via a three-component Petasis reaction. Tetrahedron Letters, 55(37), 5124–5128.
  • Cicerale, S., Lucas, L. J., & Keast, R. S. J. (2012). Antimicrobial, antioxidant and anti-inflammatory phenolic activities in extra virgin olive oil. Current Opinion in Biotechnology, 23(2), 129–135. https://doi.org/10.1016/j.copbio.2011.09.006
  • Cuenú, F., Restrepo-Acevedo, A., Isabel-Murillo, M., Eduard Torres, J., Moreno-Fuquen, R., Abonia, R., … Lehmann, C. W. (2019). Synthesis, structural characterization, and theoretical studies of new pyrazole (E)-2-{[(5-(tert-butyl)-1H-pyrazol-3-yl)imino]methyl}phenol and (E)-2-{[(1-(4-bromophenyl)-3-(tert-butyl)-1H-pyrazol-5-yl]imino]methyl}phenol. Journal of Molecular Structure, 1184, 59–71.
  • Doan, P., Nguyen, T., Yli-Harja, O., Kandhavelu, M., Yli-Harja, O., Doan, P., … Candeias, N. R. (2017). Effect of alkylaminophenols on growth inhibition and apoptosis of bone cancer cells. European Journal of Pharmaceutical Sciences, 107(July), 208–216.
  • Gomes, C. A., Girão Da Cruz, T. G., Andrade, J. L., Milhazes, N., Borges, F., & Marques, M. P. M. (2003). Anticancer Activity of Phenolic Acids of Natural or Synthetic Origin: A Structure-Activity Study. Journal of Medicinal Chemistry, 46(25), 5395–5401.
  • Hosseinzadeh, R., Lasemi, Z., Oloub, M., & Pooryousef, M. (2017). A green protocol for the one-pot multicomponent Petasis boronic Mannich reaction using ball milling. Journal of the Iranian Chemical Society, 14(2), 347–355.
  • Jesus, A. J. L., Rosado, M. T. S., Reva, I., Fausto, R., Eusébio, M. E., & Redinha, J. S. (2006). Conformational study of monomeric 2,3-butanediols by matrix-isolation infrared spectroscopy and DFT calculations. Journal of Physical Chemistry A, 110(12), 4169–4179.
  • Klopfenstein, S. R., Chen, J. J., Golebiowski, A., Li, M., Peng, S. X., & Shao, X. (2000). A practical synthesis of peptide mimetics via the solid-phase Petasis reaction. Tetrahedron Letters.
  • Kotan, G., Albayrak, Ö., & Yüksek, H. (2018). Investigation of electronic , geometric and spectroscopic properties of triazol-5-one molecule. Karadeniz Chem.Sci. Tech., 03(I), 1–7.
  • KOTAN, G., Medetalibeyoğlu, H., Beytur, M., Akyıldırım, O., & Yüksek, H. (2019). Synthesis and Theoretical Analyses of Novel 5 mercapto 2--(5 methyl furan 2 yl 1,3,4 thiadiazole Molecule. Journal of the Institute of Science and Technology, 9(2), 1023–1034. Kotan, G., & Yüksek, H. (2019). Araştırma Makalesi Research Article Spektroskopik , Geometrik , Termodinamik ve Elektronik Analizi DFT ( B3LYP / B3PW91 )/ HF of 3-Phenyl-5- ( 4-pyridyl ) -1 , 2 , 4-triazole Molecule. European Journal of Science and Technology, (17), 933–943.
  • Kucuk, I., Kaya, Y., & Kaya, A. A. (2017). Structural, spectroscopic (FT-IR, NMR, UV–visible), nonlinear optical (NLO), cytotoxic and molecular docking studies of 4-nitro-isonitrosoacetophenone (ninapH) by DFT method. Journal of Molecular Structure, 1139, 308–318.
  • Liu, Y., Wang, L., Sui, Y., & Yu, J. (2010). Solvent-free synthesis of alkylaminophenols via petasis Boronic Mannich reaction in one pot without catalysts. Chinese Journal of Chemistry, 28(10), 2039–2044.
  • Nageswari, G., George, G., Ramalingam, S., & Govindarajan, M. (2019a). Molecular analyses using FT-IR, FT-Raman and UV spectral investigation; quantum chemical calculations of dimethyl phthalate. Journal of Molecular Structure, 1195, 331–343.
  • Naseem, S., Khalid, M., Tahir, M. N., Halim, M. A., Braga, A. A. C., Naseer, M. M., & Shafiq, Z. (2017). Synthesis, structural, DFT studies, docking and antibacterial activity of a xanthene based hydrazone ligand. Journal of Molecular Structure, 1143, 235–244.
  • Neogi, S., Roy, A., & Naskar, D. (2010). One-pot synthesis of new substituted 1,2,3,4-tetrahydrocarbazoles via petasis reaction. Journal of Combinatorial Chemistry, 12(5), 617–629.
  • Petasis, N. A., & Akritopoulou, I. (1993). The boronic acid mannich reaction: A new method for the synthesis of geometrically pure allylamines. Tetrahedron Letters, 34(4), 583–586.
  • Prasad Reddy, B. R., Govardhana Reddy, P. V., Kumar, D. P., Reddy, B. N., & Shankar, M. V. (2016). Rapid synthesis of alkylaminophenols via the Petasis borono-Mannich reaction using protonated trititanate nanotubes as robust solid-acid catalysts. RSC Advances, 6(18), 14682–14691.
  • Raja, M., Muhamed, R. R., Muthu, S., & Suresh, M. (2017a). Synthesis, spectroscopic (FT-IR, FT-Raman, NMR, UV–Visible), first order hyperpolarizability, NBO and molecular docking study of (E)-1-(4-bromobenzylidene)semicarbazide. Journal of Molecular Structure, 1128, 481–492.
  • Shi, X., Hebrault, D., Humora, M., Kiesman, W. F., Peng, H., Talreja, T., … Xin, Z. (2012). Acceleration of Petasis reactions of salicylaldehyde derivatives with molecular sieves. Journal of Organic Chemistry, 77(2), 1154–1160.
  • Sundaraganesan, N., Ilakiamani, S., Saleem, H., Wojciechowski, P. M., & Michalska, D. (2005). FT-Raman and FT-IR spectra, vibrational assignments and density functional studies of 5-bromo-2-nitropyridine. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 61(13–14), 2995–3001.
  • Tremblay-Morin, J. P., Raeppel, S., & Gaudette, F. (2004). Lewis acid-catalyzed Mannich type reactions with potassium organotrifluoroborates. Tetrahedron Letters, 45(17), 3471–3474.
  • Ulaş, Y. (2019). Akıllı Malzemelerin Hazırlanmasında Kullanılacak Amin Türevi Monomerlerin Sentez ve Karakterizasyonu. European Journal of Science and Technology, 16, 242–246.
  • Ulaş, Y., Özkan, A. İ., & Tolan, V. (2019). Yeni p-alkilaminofenol Bileşiklerinin Sentezi ve Antimikrobiyal ve Antioksidan Aktivitelerinin Araştırılması. European Journal of Science and Technology, 16, 701–706.
  • Wang, J., Li, P., Shen, Q., & Song, G. (2014). Concise synthesis of aromatic tertiary amines via a double Petasis-borono Mannich reaction of aromatic amines, formaldehyde, and organoboronic acids. Tetrahedron Letters, 55(29), 3888–3891.
  • Wolinski, K., Hinton, J. F., & Pulay, P. (1990). Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. Journal of the American Chemical Society, 112(23), 8251–8260.
  • Wu, P., Givskov, M., & Nielsen, T. E. (2019). Reactivity and Synthetic Applications of Multicomponent Petasis Reactions. Chemical Reviews, 119(20), 11245–11290.
  • Yu, A., Wu, Y., Cheng, B., Wei, K., & Li, J. (2009). A mild, one-pot synthesis of arylamines via palladium-catalyzed addition of aryl aldehydes with amines and arylboronic acids in water. Advanced Synthesis and Catalysis, 351(5), 767–771.

Synthesis of 2-(Azepan-1-yl(naphthalen-1-yl)methyl)phenol Compound and Quantum Chemical Calculations

Yıl 2020, Sayı: 18, 574 - 582, 15.04.2020
https://doi.org/10.31590/ejosat.682673

Öz

The 2-(Azepan-1-yl(naphthalen-1-yl)methyl)phenol compound is an alkylaminophenol compound and has been experimentally synthesized by the petasis reaction. In this study, structural analysis was done by FT-IR, NMR, UV-Vis spectroscopy. In order to support experimental data with theoretical data, many physicochemical parameters of the compound were investigated with 6-311G ++ (d, p) set and DFT (B3LYP) method. Electronic and structural properties of the compound (bond lengths, bond angles and dihedral angles), HOMO (highest occupied molecular orbital) and LUMO (lowest empty molecular orbital) energies, electrostatic potential (MEP), vibration frequencies, Mulliken atomic charges, excitation energies and oscillator strengths were calculated. Theoretical values and experimental values were found to be compatible, and information was given about the source and causes of existing deviations.

Proje Numarası

KUAP(F)-2016/5

Kaynakça

  • Becke, A. D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38(6), 3098–3100.
  • Beisel, T., & Manolikakes, G. (2015). Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Substituted Amines. Organic Letters, 17(12), 3162–3165.
  • Borisov, Y. A., & Akhrem, I. S. (2019). DFT B3LYP/6-311+G* calculation study of a new nonclassical mechanism of electrophilic functionalization of aromatic C–H bond via aryl cation formation. Mendeleev Communications, 29(3), 343–345.
  • Candeias, N. R., Montalbano, F., Cal, P. M. S. D., & Gois, P. M. P. (2010). Boronic acids and esters in the petasis-borono mannich multicomponent reaction. Chemical Reviews, 110(10), 6169–6193.
  • Chouguiat, L., Boulcina, R., Carboni, B., Demonceau, A., & Debache, A. (2014). A new and efficient one-pot synthesis of 2-hydroxy-1,4-dihydrobenzoxazines via a three-component Petasis reaction. Tetrahedron Letters, 55(37), 5124–5128.
  • Cicerale, S., Lucas, L. J., & Keast, R. S. J. (2012). Antimicrobial, antioxidant and anti-inflammatory phenolic activities in extra virgin olive oil. Current Opinion in Biotechnology, 23(2), 129–135. https://doi.org/10.1016/j.copbio.2011.09.006
  • Cuenú, F., Restrepo-Acevedo, A., Isabel-Murillo, M., Eduard Torres, J., Moreno-Fuquen, R., Abonia, R., … Lehmann, C. W. (2019). Synthesis, structural characterization, and theoretical studies of new pyrazole (E)-2-{[(5-(tert-butyl)-1H-pyrazol-3-yl)imino]methyl}phenol and (E)-2-{[(1-(4-bromophenyl)-3-(tert-butyl)-1H-pyrazol-5-yl]imino]methyl}phenol. Journal of Molecular Structure, 1184, 59–71.
  • Doan, P., Nguyen, T., Yli-Harja, O., Kandhavelu, M., Yli-Harja, O., Doan, P., … Candeias, N. R. (2017). Effect of alkylaminophenols on growth inhibition and apoptosis of bone cancer cells. European Journal of Pharmaceutical Sciences, 107(July), 208–216.
  • Gomes, C. A., Girão Da Cruz, T. G., Andrade, J. L., Milhazes, N., Borges, F., & Marques, M. P. M. (2003). Anticancer Activity of Phenolic Acids of Natural or Synthetic Origin: A Structure-Activity Study. Journal of Medicinal Chemistry, 46(25), 5395–5401.
  • Hosseinzadeh, R., Lasemi, Z., Oloub, M., & Pooryousef, M. (2017). A green protocol for the one-pot multicomponent Petasis boronic Mannich reaction using ball milling. Journal of the Iranian Chemical Society, 14(2), 347–355.
  • Jesus, A. J. L., Rosado, M. T. S., Reva, I., Fausto, R., Eusébio, M. E., & Redinha, J. S. (2006). Conformational study of monomeric 2,3-butanediols by matrix-isolation infrared spectroscopy and DFT calculations. Journal of Physical Chemistry A, 110(12), 4169–4179.
  • Klopfenstein, S. R., Chen, J. J., Golebiowski, A., Li, M., Peng, S. X., & Shao, X. (2000). A practical synthesis of peptide mimetics via the solid-phase Petasis reaction. Tetrahedron Letters.
  • Kotan, G., Albayrak, Ö., & Yüksek, H. (2018). Investigation of electronic , geometric and spectroscopic properties of triazol-5-one molecule. Karadeniz Chem.Sci. Tech., 03(I), 1–7.
  • KOTAN, G., Medetalibeyoğlu, H., Beytur, M., Akyıldırım, O., & Yüksek, H. (2019). Synthesis and Theoretical Analyses of Novel 5 mercapto 2--(5 methyl furan 2 yl 1,3,4 thiadiazole Molecule. Journal of the Institute of Science and Technology, 9(2), 1023–1034. Kotan, G., & Yüksek, H. (2019). Araştırma Makalesi Research Article Spektroskopik , Geometrik , Termodinamik ve Elektronik Analizi DFT ( B3LYP / B3PW91 )/ HF of 3-Phenyl-5- ( 4-pyridyl ) -1 , 2 , 4-triazole Molecule. European Journal of Science and Technology, (17), 933–943.
  • Kucuk, I., Kaya, Y., & Kaya, A. A. (2017). Structural, spectroscopic (FT-IR, NMR, UV–visible), nonlinear optical (NLO), cytotoxic and molecular docking studies of 4-nitro-isonitrosoacetophenone (ninapH) by DFT method. Journal of Molecular Structure, 1139, 308–318.
  • Liu, Y., Wang, L., Sui, Y., & Yu, J. (2010). Solvent-free synthesis of alkylaminophenols via petasis Boronic Mannich reaction in one pot without catalysts. Chinese Journal of Chemistry, 28(10), 2039–2044.
  • Nageswari, G., George, G., Ramalingam, S., & Govindarajan, M. (2019a). Molecular analyses using FT-IR, FT-Raman and UV spectral investigation; quantum chemical calculations of dimethyl phthalate. Journal of Molecular Structure, 1195, 331–343.
  • Naseem, S., Khalid, M., Tahir, M. N., Halim, M. A., Braga, A. A. C., Naseer, M. M., & Shafiq, Z. (2017). Synthesis, structural, DFT studies, docking and antibacterial activity of a xanthene based hydrazone ligand. Journal of Molecular Structure, 1143, 235–244.
  • Neogi, S., Roy, A., & Naskar, D. (2010). One-pot synthesis of new substituted 1,2,3,4-tetrahydrocarbazoles via petasis reaction. Journal of Combinatorial Chemistry, 12(5), 617–629.
  • Petasis, N. A., & Akritopoulou, I. (1993). The boronic acid mannich reaction: A new method for the synthesis of geometrically pure allylamines. Tetrahedron Letters, 34(4), 583–586.
  • Prasad Reddy, B. R., Govardhana Reddy, P. V., Kumar, D. P., Reddy, B. N., & Shankar, M. V. (2016). Rapid synthesis of alkylaminophenols via the Petasis borono-Mannich reaction using protonated trititanate nanotubes as robust solid-acid catalysts. RSC Advances, 6(18), 14682–14691.
  • Raja, M., Muhamed, R. R., Muthu, S., & Suresh, M. (2017a). Synthesis, spectroscopic (FT-IR, FT-Raman, NMR, UV–Visible), first order hyperpolarizability, NBO and molecular docking study of (E)-1-(4-bromobenzylidene)semicarbazide. Journal of Molecular Structure, 1128, 481–492.
  • Shi, X., Hebrault, D., Humora, M., Kiesman, W. F., Peng, H., Talreja, T., … Xin, Z. (2012). Acceleration of Petasis reactions of salicylaldehyde derivatives with molecular sieves. Journal of Organic Chemistry, 77(2), 1154–1160.
  • Sundaraganesan, N., Ilakiamani, S., Saleem, H., Wojciechowski, P. M., & Michalska, D. (2005). FT-Raman and FT-IR spectra, vibrational assignments and density functional studies of 5-bromo-2-nitropyridine. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 61(13–14), 2995–3001.
  • Tremblay-Morin, J. P., Raeppel, S., & Gaudette, F. (2004). Lewis acid-catalyzed Mannich type reactions with potassium organotrifluoroborates. Tetrahedron Letters, 45(17), 3471–3474.
  • Ulaş, Y. (2019). Akıllı Malzemelerin Hazırlanmasında Kullanılacak Amin Türevi Monomerlerin Sentez ve Karakterizasyonu. European Journal of Science and Technology, 16, 242–246.
  • Ulaş, Y., Özkan, A. İ., & Tolan, V. (2019). Yeni p-alkilaminofenol Bileşiklerinin Sentezi ve Antimikrobiyal ve Antioksidan Aktivitelerinin Araştırılması. European Journal of Science and Technology, 16, 701–706.
  • Wang, J., Li, P., Shen, Q., & Song, G. (2014). Concise synthesis of aromatic tertiary amines via a double Petasis-borono Mannich reaction of aromatic amines, formaldehyde, and organoboronic acids. Tetrahedron Letters, 55(29), 3888–3891.
  • Wolinski, K., Hinton, J. F., & Pulay, P. (1990). Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. Journal of the American Chemical Society, 112(23), 8251–8260.
  • Wu, P., Givskov, M., & Nielsen, T. E. (2019). Reactivity and Synthetic Applications of Multicomponent Petasis Reactions. Chemical Reviews, 119(20), 11245–11290.
  • Yu, A., Wu, Y., Cheng, B., Wei, K., & Li, J. (2009). A mild, one-pot synthesis of arylamines via palladium-catalyzed addition of aryl aldehydes with amines and arylboronic acids in water. Advanced Synthesis and Catalysis, 351(5), 767–771.
Toplam 31 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Yeliz Ulaş 0000-0003-2038-1851

Proje Numarası KUAP(F)-2016/5
Yayımlanma Tarihi 15 Nisan 2020
Yayımlandığı Sayı Yıl 2020 Sayı: 18

Kaynak Göster

APA Ulaş, Y. (2020). 2- (azepan-1-il (naftalen-1-il) metil)fenol Bileşiğinin Sentezi ve Kuantum Kimyasal Hesaplamaları. Avrupa Bilim Ve Teknoloji Dergisi(18), 574-582. https://doi.org/10.31590/ejosat.682673