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Molecular Physics
An International Journal at the Interface Between Chemistry and Physics
Volume 118, 2020 - Issue 6
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Research Articles

Mechanistic study of the formation of quercetine cycloadducts under microwave conditions: a theoretical approach

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Article: e1643509 | Received 08 Mar 2019, Accepted 04 Jul 2019, Published online: 14 Oct 2019

References

  • A.N. Panche, A.D. Diwan and S.R. Chandra, J. Nutr. Sci. 5, 1–15 (2016). doi: 10.1017/jns.2016.41
  • N. Masuoka, M. Matsuda and I. Kubo, Food Chem. 131, 541–545 (2012). doi: 10.1016/j.foodchem.2011.09.020
  • A. Zhou and O.A. Sadik, J. Agric. Food Chem. 56, 12081–12091 (2008). doi: 10.1021/jf802413v
  • V. Krishnamachari, L.H. Levine, C. Zhou and P.W. Paré, Chem. Res. Toxicol. 17, 795–804 (2004). doi: 10.1021/tx034242z
  • E.M. Cherviakovsky, D.A. Bolibrukh, A.V. Baranovsky, T.M. Vlasova, V.P. Kurchenko, A.A. Gilep and S.A. Usanov, Biochem. Biophys. Res. Commun. 342, 459–464 (2006). doi: 10.1016/j.bbrc.2006.02.001
  • A. Gülşen, D.P. Makris and P. Kefalas, Food Res. Int. 40, 7–14 (2007). doi: 10.1016/j.foodres.2006.07.009
  • A. Osman and D.P. Makris, Int. J. Food Sci. Technol. 45, 2265–2271 (2010). doi: 10.1111/j.1365-2621.2010.02408.x
  • J. Kaizer, G. Speier, E. Osz, M. Giorgi and M. Réglier, Tetrahedron Lett. 45, 8011–8013 (2004). doi: 10.1016/j.tetlet.2004.09.009
  • A. De La Hoz, A. Díaz-Ortis, A. Moreno and F. Langa, European J. Org. Chem. 2000, 3659–3673 (2000). doi: 10.1002/1099-0690(200011)2000:22<3659::AID-EJOC3659>3.0.CO;2-0
  • A. De la Hoz, A. Díaz-Ortiz and A. Moreno, Curr. Org. Chem. 8, 903–918 (2004). doi: 10.2174/1385272043370429
  • F. Langa, P. de la Cruz, A. de la Hoz, A. Díaz-Ortiz and E. Díez-Barra, Contemp. Org. Synth. 4, 373–386 (1997). doi: 10.1039/CO9970400373
  • D. Cáceres-Castillo, F. Moguel-Pardío, R.F. Quijano-Quiñones, G. Mirón-López and G.J. Mena-Rejón, Lett. Org. Chem. 13, 107–112 (2016). doi: 10.2174/1570178612666151008014708
  • R.E. Plata and D.A. Singleton, J. Am. Chem. Soc. 137, 3811–3826 (2015). doi: 10.1021/ja5111392
  • Y. Tobe, J.-Y. Kishi, I. Ohki and M. Sonoda, J. Org. Chem. 68, 3330–3332 (2003). doi: 10.1021/jo0268299
  • L.R. Domingo and J. Andre, J. Org. Chem. 68, 8662–8668 (2003). doi: 10.1021/jo030156s
  • Y. Zhao and D.G. Truhlar, Acc. Chem. Res. 41, 157–167 (2008). doi: 10.1021/ar700111a
  • S.N. Pieniazek, F.R. Clemente and K.N. Houk, Angew. Chemie. Int. Ed. 47, 7746–7749 (2008). doi: 10.1002/anie.200801843
  • E.G. Hohenstein, S.T. Chill, C.D. Sherrill and J. Chem, Theory Comput. 4, 1996–2000 (2008). doi: 10.1021/ct800308k
  • K. Ramírez-Gualito, N. López-Mora, H.A. Jiménez-Vázquez, J. Tamariz and G. Cuevas, J. Mex. Chem. Soc. 57, 267–275 (2013).
  • K. Fukui, Acc. Chem. Res. 14, 363–368 (1981). doi: 10.1021/ar00072a001
  • J. Tomasi, B. Mennucci and R. Cammi, Chem. Rev. 105, 2999–3094 (2005). doi: 10.1021/cr9904009
  • M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, G.A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B.G. Janesko, R. Gomperts, B. Mennucci, H.P. Hratchian, J.V. Ortiz, A.F. Izmaylov, J.L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V.G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, J.M. Millam, M. Klene, C. Adamo, R. Cammi, J.W. Ochterski, R.L. Martin, K. Morokuma, O. Farkas, J.B. Foresman and D.J. Fox. Gaussian 09, Revision A.1 (Gaussian, Inc. Wallingford, CT, 2009).
  • M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, G.A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A.V. Marenich, J. Bloino, B.G. Janesko, R. Gomperts, B. Mennucci, H.P. Hratchian, J.V. Ortiz, A.F. Izmaylov, J.L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V.G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M.J. Bearpark, J.J. Heyd, E.N. Brothers, K.N. Kudin, V.N. Staroverov, T.A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A.P. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, J.M. Millam, M. Klene, C. Adamo, R. Cammi, J.W. Ochterski, R.L. Martin, K. Morokuma, O. Farkas, J.B. Foresman and D.J. Fox, Gaussian 16, Revision A.03 (Gaussian, Inc., Wallingford, CT, 2016).
  • J. Contreras-García, E.R. Johnson, S. Keinan, R. Chaudret, J.-P. Piquemal, D.N. Beratan and W. Yang, J. Chem. Theory Comput. 7, 625–632 (2011). doi: 10.1021/ct100641a
  • W. Humphrey, A. Dalke and K. Schulten, J. Mol. Graph. 14, 33–38 (1996). doi: 10.1016/0263-7855(96)00018-5
  • R.G. Parr, L.V. Szentpály and S. Liu, J. Am. Chem. Soc. 121, 1922–1924 (1999). doi: 10.1021/ja983494x
  • L.R. Domingo, E. Chamorro and P. Pérez, J. Org. Chem. 73, 4615–4624 (2008). doi: 10.1021/jo800572a
  • L.R. Domingo, M. Ríos-Gutiérrez and P. Pérez, Molecules. 21, 1–22 (2016).
  • N. Mardirossian and M. Head-Gordon, Mol. Phys. 115, 2315–2372 (2017). doi: 10.1080/00268976.2017.1333644
  • L. Goerigk, A. Hansen, C. Bauer, S. Ehrlich, A. Najibi and S. Grimme, Phys. Chem. Chem. Phys. 19, 32184–32215 (2017). doi: 10.1039/C7CP04913G
  • A. De Cózar, M.C. Millán, C. Cebrián, P. Prieto, A. Díaz-Ortiz, A. de la Hoz and F.P. Cossío, Org. Biomol. Chem. 8, 1000–1009 (2010). doi: 10.1039/b922730j
  • L. Perreux and A. Loupy, Tetrahedron. 57, 9199–9223 (2001). doi: 10.1016/S0040-4020(01)00905-X
  • M.V. Gómez, A.I. Aranda, A. Moreno, F.P. Cossío, A. de Cózar, Á Díaz-Ortiz, A. de la Hoz and P. Prieto, Tetrahedron. 65, 5328–5336 (2009). doi: 10.1016/j.tet.2009.04.065
  • K. Huang, X. Yang, W. Hua, G. Jia and L. Yang, New J. Chem. 33, 1486–1489 (2009). doi: 10.1039/b821970b
  • F. Weinhold and C.R. Landis, Chem. Educ. Res. Pract. Eur. 2, 91–104 (2001). doi: 10.1039/B1RP90011K
  • L.R. Domingo, M.J. Aurell, P. Pérez and R. Contreras, Tetrahedron. 58, 4417–4423 (2002). doi: 10.1016/S0040-4020(02)00410-6
  • L.R. Domingo, M. Ríos-Gutiérrez, B. Silvi and P. Pérez, European J. Org. Chem. 2018, 1107–1120 (2018). doi: 10.1002/ejoc.201701350
  • C.B. Shinisha and R.B. Sunoj, Org. Biomol. Chem. 6, 3921–3929 (2008). doi: 10.1039/b810901j
  • M. Terada, K. Soga and N. Momiyama, Angew. Chemie. Int. Ed. 47, 4122–4125 (2008). doi: 10.1002/anie.200800232
  • D. Janardanan and R.B. Sunoj, J. Org. Chem. 73, 8163–8174 (2008). doi: 10.1021/jo800652c
  • M.P. Patil, A.K. Sharma and R.B. Sunoj, J. Org. Chem. 75, 7310–7321 (2010). doi: 10.1021/jo101592b
  • C.B. Shinisha and R.B. Sunoj, Org. Lett. 12, 2868–2871 (2010). doi: 10.1021/ol100969f
  • A.K. Sharma and R.B. Sunoj, Chem. Commun. 47, 5759–5761 (2011). doi: 10.1039/c1cc11063b
  • A.Z. González, D. Benitez, E. Tkatchouk, W.A. Goddard and F.D. Toste, J. Am. Chem. Soc. 133, 5500–5507 (2011). doi: 10.1021/ja200084a
  • H. Yang and M.W. Wong, J. Am. Chem. Soc. 135, 5808–5818 (2013). doi: 10.1021/ja4005893
  • I. Čorić, J.H. Kim, T. Vlaar, M. Patil, W. Thiel and B. List, Angew. Chemie. Int. Ed. 52, 3490–3493 (2013). doi: 10.1002/anie.201209983
  • I.A. Sanhueza, A.M. Wagner, M.S. Sanford and F. Schoenebeck, Chem. Sci. 4, 2767–2775 (2013). doi: 10.1039/c3sc00017f
  • M. Orlandi, J.A.S. Coelho, M.J. Hilton, F.D. Toste and M.S. Sigman, J. Am. Chem. Soc. 139, 6803–6806 (2017). doi: 10.1021/jacs.7b02311

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