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Synthesis, Characterization, DFT Studies of Novel Phase Transfer Catalyst and Application in O-Propargylation Reaction
Corresponding Author(s) : S. Rani
Asian Journal of Chemistry,
Vol. 35 No. 4 (2023): Vol 35 Issue 4, 2023
Abstract
The present work reports the synthesis and characterization of 1-benzyl-1,4-diazoniabicyclo[2.2.1]hepta-2,4(7)-diene dibromide for phase transfer catalyst (PTC) applications. The derived quaternary salt was characterized by UV, FTIR and NMR spectral techniques. The structure has been optimized by density functional theory (DFT) in water and diethyl ether solvation conditions. The DFT outcomes showed the good chemical potential of the compound between 2.15 eV and 6.8 eV in both media. Extended research examined the nature of phase transfer by adjusting dosage, temperature and solvents in the O-propargylation reaction under normal conditions for useful precursor synthesis. The kinetic data revealed that the novel bisite quaternary amine bromide salt was effective in a variety of conditions. The chlorobenzene and water biphasic system yielded 88% of bioactive molecule precursor when compare to other immiscible systems.
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- O.V. Kharissova, B.I. Kharisov, C.M. Oliva-González, Y. Peña-Méndez and I. López, R. Soc. Open Sci., 6, 191378 (2019); https://doi.org/10.1098/rsos.191378
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- T.T. Adejumo, N.V. Tzouras, L.P. Zorba, D. Radanovic, S. Grubisic, A. Pevec, D. Mitic, K.K. Andelkovic, G.C. Vougioukalakis, B. Cobeljic and I. Turel, Molecules, 25, 4043 (2020); https://doi.org/10.3390/molecules25184043
- M. Boz and S.S. Basturk, J. Surfactants Deterg., 19, 663 (2016); https://doi.org/10.1007/s11743-016-1821-z
- R. Jayaprakash, S.K. Sha, S. Hemalatha and D. Easwaramoorthy, Int. J. Chemtech Res., 9, 48 (2016).
- V. Selvaraj and V. Rajendran, Ultrason. Sonochem., 21, 612 (2014); https://doi.org/10.1016/j.ultsonch.2013.09.013
- N. Ayashi, M. Fallah-Mehrjardi and A.R. Kiasat, Russ. J. Org. Chem., 53, 846 (2017); https://doi.org/10.1134/S1070428017060069
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References
O.V. Kharissova, B.I. Kharisov, C.M. Oliva-González, Y. Peña-Méndez and I. López, R. Soc. Open Sci., 6, 191378 (2019); https://doi.org/10.1098/rsos.191378
T.A. Hamlin, M. Swart and F.M. Bickelhaupt, ChemPhysChem, 19, 1315 (2018); https://doi.org/10.1002/cphc.201701363
G. Pupo, F. Ibba, D.M.H. Ascough, A.C. Vicini, K.E. Christensen, P. Ricci, L. Pfeifer, J.R. Morphy, J.M. Brown, R.S. Paton and V. Gouverneur, Science, 360, 638 (2018); https://doi.org/10.1126/science.aar7941
M. M¹kosza and M. Fedoryñski, Catal. Rev., Sci. Eng., 45, 321 (2003); https://doi.org/10.1081/CR-120025537
S. Shirakawa and K. Maruoka, Angew. Chem. Int. Ed. Engl., 52, 4312 (2013); https://doi.org/10.1002/anie.201206835
C.M. Starks, J. Am. Chem. Soc., 93, 195 (1971); https://doi.org/10.1021/ja00730a033
K. Urata and N. Takaishi, J. Am. Oil Chem. Soc., 73, 831 (1996); https://doi.org/10.1007/BF02517983
S.D. Naik and L.K. Doraiswamy, AIChE J., 44, 612 (1998); https://doi.org/10.1002/aic.690440312
S. Liu and W. Zhu, Biomed. J. Sci. Technol. Res., 45, 36691 (2022); https://doi.org/10.26717/BJSTR.2022.45.007237
S.P. Neofotistos, A. Tzani and A. Detsi, Catalysts, 13, 474 (2023); https://doi.org/10.3390/catal13030474
D.R. Fandrick, J. Saha, K.R. Fandrick, S. Sanyal, H. Lee, F. Roschangar, J. Ogikubo, J.J. Song and C.H. Senanayake, Org. Lett., 13, 5616 (2011); https://doi.org/10.1021/ol202343c
G. Zweifel, S.J. Backlund and T. Leung, J. Am. Chem. Soc., 100, 5561 (1978); https://doi.org/10.1021/ja00485a049
J. Xiao, M. Khan, A. Singh, E. Suljoti, L. Spiccia and E.F. Aziz, ChemSusChem, 8, 872 (2015); https://doi.org/10.1002/cssc.201403219
T.T. Adejumo, N.V. Tzouras, L.P. Zorba, D. Radanovic, S. Grubisic, A. Pevec, D. Mitic, K.K. Andelkovic, G.C. Vougioukalakis, B. Cobeljic and I. Turel, Molecules, 25, 4043 (2020); https://doi.org/10.3390/molecules25184043
M. Boz and S.S. Basturk, J. Surfactants Deterg., 19, 663 (2016); https://doi.org/10.1007/s11743-016-1821-z
R. Jayaprakash, S.K. Sha, S. Hemalatha and D. Easwaramoorthy, Int. J. Chemtech Res., 9, 48 (2016).
V. Selvaraj and V. Rajendran, Ultrason. Sonochem., 21, 612 (2014); https://doi.org/10.1016/j.ultsonch.2013.09.013
N. Ayashi, M. Fallah-Mehrjardi and A.R. Kiasat, Russ. J. Org. Chem., 53, 846 (2017); https://doi.org/10.1134/S1070428017060069
P.A. Vivekanand and T. Balakrishnan, Appl. Catal. A Gen., 364, 27 (2009); https://doi.org/10.1016/j.apcata.2009.05.014
C. Li and J. Wang, J. Org. Chem., 72, 7431 (2007); https://doi.org/10.1021/jo0709192