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

Year 2022, Volume: 9 Issue: 2, 184 - 195, 31.12.2022
https://doi.org/10.48138/cjo.1205002

Abstract

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

References

  • 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.

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

Year 2022, Volume: 9 Issue: 2, 184 - 195, 31.12.2022
https://doi.org/10.48138/cjo.1205002

Abstract

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.

References

  • 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.
There are 25 citations in total.

Details

Primary Language Turkish
Subjects Environmental Sciences
Journal Section Articles
Authors

Yeliz Ulaş 0000-0003-2038-1851

Publication Date December 31, 2022
Submission Date November 15, 2022
Acceptance Date December 29, 2022
Published in Issue Year 2022 Volume: 9 Issue: 2

Cite

APA Ulaş, Y. (2022). 2-((1H-indol-1-il)(naftalen-1-il)metil)fenol Bileşiğinin Sentezi ve NLO Özelliklerinin Quantum Kimyasal Hesaplamalarla İncelenmesi. Caucasian Journal of Science, 9(2), 184-195. https://doi.org/10.48138/cjo.1205002

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