2-((1H-indol-1-il)(naftalen-1-il)metil)fenol Bileşiğinin Sentezi ve NLO Özelliklerinin Quantum Kimyasal Hesaplamalarla İncelenmesi

Bu çalışmada, 2-((1H-indol-1-il)(naftalen-1-il)metil)fenol bileşiği ilk kez sentezlenmiş olup, yapısal analizi 1H-NMR, 13C-NMR, FT-IR gibi spektroskopik yöntemlerle deneysel ve teorik olarak incelenmiştir. Bileşiğe ait birçok özellik; spektral veriler, bağ uzunluğu, bağ açısı, dihedral açıları, molekül yüzeyi, FMO analizi ve doğrusal olmayan optik (NLO) özellikleri de teorik olarak araştırılmıştır. Hesaplamalar; HF ve DFT/B3LYP metotları ile 6-311++G(d,p) temel seti kullanılarak gerçekleştirilmiştir. Elde edilen veriler ışığında, alkilaminofenollerin, medikal uygulamalar haricinde optoelektronik alanda da kullanılabileceği ön görülmüştür

Anahtar Kelimeler:

Alkilaminofenol; NLO; DFT

Synthesis of 2-((1H-indol-1-yl)(naphthalen-1-yl)methyl)phenol Compound and Investigation of NLO Properties by Quantum Chemical Calculations

Keywords:

Alkylaminophenol, NLO, DFT Alkilaminofenol; NLO; DFT,

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Becke, A.D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A., 38, 3098–3100.
Bouillon, A., Lancelot, J.C., Collot, V., Bovy, P.R., Rault, S.( 2002). Synthesis of novel halopyridinylboronic acids and esters., Part 3: 2, or 3-Halopyridin-4-yl-boronic acids and esters. Tetrahedron, 58, 4369–4373.
Candeias, N.R., Montalbano, F., Cal, Pedro M.S.D., Gois, Pedro M.P. (2010). Boronic acids and esters in the petasis-borono mannich multicomponent reaction, Chem. Rev., 110, 6169–6193.
Doan, P., Nguyen, T., Yli-Harja, O., Kandhavelu, M., Yli-Harja, O., Doan, P., Nguyen, T., Tien, Y., Olli, C., Nuno R. (2017). Effect of alkylaminophenols on growth inhibition and apoptosis of bone cancer cells. Eur. J. Pharm. Sci., 107, 208–216.
Govindarajan, M., Karabacak, M, Periandy, S., Tanuja, D. (2012). Spectroscopic (FT-IR, FT-Raman, UV and NMR) investigation and NLO, HOMO-LUMO, NBO analysis of organic 2,4,5-trichloroaniline. Spectrochim. Acta - Part A Mol. Biomol. Spectrosc., 97, 231–245.
Guidara, S., Feki, H., Abid, Y. (2015). Structural, vibrational, NLO, MEP, NBO analysis and DFT calculation of bis 2,5-dimethylanilinium sulfate.J. Mol. Struct., 1080, 176–187.
Han, W.Y., Wu, Z.J., Zhang, X.M., Yuan, W.C. (2012). Enantioselective organocatalytic three-component petasis reaction among salicylaldehydes, amines, and organoboronic acids. Org. Lett., 14, 976–979.
Koç, E., Yüksek, H., Beytur, M., Akyıldırım, O., Akçay, M., Beytur, C. (2020). In vivo determination of antioxidant property of heterocyclic 4,5 dihydro-1H-1, 2, 4- triazol 5-one derivate in male rats (wistar albino). Bitlis Eren University Journal of Science, 9, 542-548.
Koolmeister, T., Södergren, M., Scobie, M. (2002). Pinacolyl boronic esters as components in the Petasis reaction. Tetrahedron Lett., 43, 5965–5968.
Mathammal, R., Sangeetha, K., Sangeetha, M., Mekala, R., Gadheeja,S. (2016). Molecular structure, vibrational, UV, NMR, HOMO-LUMO, MEP, NLO, NBO analysis of 3,5 di tert butyl 4 hydroxy benzoic acid. J. Mol. Struct., 1120, 1-14.
Muthu, S., Elamurugu Porchelvi, E., Karabacak, M., Asiri, A. M., Swathi, S.S. (2015). Synthesis, structure, spectroscopic studies (FT-IR, FT-Raman and UV), normal coordinate, NBO and NLO analysis of salicylaldehyde p-chlorophenylthiosemicarbazone. J. Mol. Struct., 1081, 400–412.
Neto, İ., Andrade, J., Fernandes, A. S., Pinto Reis, C., Salunge, J. K., Priimagi, A., Candeias, N. R., Rijo, P. (2016). Multicomponent Petasis-borono Mannich Preparation of Alkylaminophenols and Antimicrobial Activity Studies. ChemMedChem., 11, 2015–2023.
Petasis, N.A., Goodman, A., Zavialov, I.A. (1997). A new synthesis of α-arylglycines from aryl boronic acids. Tetrahedron, 53,16463–16470.
Portlock, D. E., Naskar, D.,West, L.,Li, M. (2002). Petasis boronic acid-Mannich reactions of substituted hydrazines: Synthesis of α-hydrazinocarboxylic acids. Tetrahedron Lett., 43, 6845–6847.
Raja, M., Muhamed, R. R., Muthu, S., Suresh, M. (2017). Synthesis, spectroscopic (FT-IR, FT-Raman, NMR, UV–Visible), NLO, NBO, HOMO-LUMO, Fukui function and molecular docking study of (E)-1-(5-bromo-2-hydroxybenzylidene)semicarbazide. J. Mol. Struct., 1141, 284–298.
Shi, X., Hebrault, D., Humora, M., Kiesman, W.F. Peng, H., Talreja, T., Wang, Z., Xin, Z. (2012). Acceleration of Petasis reactions of salicylaldehyde derivatives with molecular sieves. J. Org. Chem., 77, 1154–1160.
Souza, R. Y., Bataglion, G. A., Ferreira, D.A.C., Gatto, C. C., Eberlin, M.N., Neto, B.A.D. (2015). Insights on the Petasis Borono-Mannich multicomponent reaction mechanism. RSC Adv., 5, 76337–76341.
Takahashi, N., Ohba, T., Yamauchi, T., Higashiyama, K. (2006). Antioxidant and anticancer activities of novel p-alkylaminophenols and p-acylaminophenols (aminophenol analogues). Bioorganic Med. Chem., 14 (17), 6089–6096.
Tao, C.Z., Zhang, Z.T., Wu, J.W., Li, R.H., Cao, Z.L. (2014). Synthesis of unnatural N-glycosyl α-amino acids via Petasis reaction. Chinese Chem. Lett., 25, 532–534.
Ulaş, Y. (2021). Synthesis, Spectroscopic Characterization (FT-IR, NMR, UV), NPA, NBO, NLO, Thermochemical Analysis and Molecular Docking Studies of 2-((4-hydroxyphenyl)(piperidin-1-yl)methyl)phenol, Journal Of Theoretical & Computational Chemistry, 20, 323-335.
Ulaş, Y. (2022). Use of Anilines in the Petasis Reaction: DFT Mechanistic Study, Russian Journal Of Organic Chemistry, 58, 419-427.
Wang, R., Xu, J. (2010). Selective alkylation of aminophenols. Arkivoc, 2010, 293–299.
Wu, P., Givskov, M., Nielsen, T.E. (2019). Reactivity and Synthetic Applications of Multicomponent Petasis Reactions. Chem. Rev., 119, 11245–11290.
Xu, L., Zhang, S., Li, P. (2015). Boron-selective reactions as powerful tools for modular synthesis of diverse complex molecules. Reviews, 44 (24.), 8848–8858.
Yang, X., Cao, Z.H. Zhou, Y., Cheng, F., Lin, Z.W., Ou, Z., Yuan, Y.,Huang, Y.Yong (2018). Petasis-Type gem-Difluoroallylation Reactions Assisted by the Neighboring Hydroxyl Group in Amines: rapid-communication. Org. Lett, 20, 2585–2589.