Full-text resources of PSJD and other databases are now available in the new Library of Science.
Visit https://bibliotekanauki.pl


Preferences help
enabled [disable] Abstract
Number of results


2013 | 11 | 3 | 404-412

Article title

The reaction mechanism of the [2+3] cycloaddition between α-phenylnitroethene and (Z)-C,N-diphenylnitrone in the light of a B3LYP/6-31G(d) computational study


Title variants

Languages of publication



Abstract The analysis of reactivity indices suggests the polar nature of the [2+3] cycloaddition of a-phenylnitroethene to (Z)-C,N-diphenylnitrone. Similar conclusions can be drawn from the investigation of the reaction pathways using the B3LYP/6-31g(d) algorithm. This shows that the cycloaddition mechanism depends on the polarity of the reaction medium. A one-step mechanism is followed in the gas phase and toluene in all the theoretically possible pathways. In more polar media (nitromethane, water), a zwitterionic, two-step rather than a one-step mechanism occurs in the pathway leading to 3,4-trans-2,3,5-triphenyl-4-nitroisoxazolidine. Graphical abstract [...]










Physical description


1 - 3 - 2013
28 - 12 - 2012


  • Institute of Organic Chemistry and Technology, Cracow University of Technology, 31155, Cracow, Poland
  • Institute of Organic Chemistry and Technology, Cracow University of Technology, 31155, Cracow, Poland
  • Institute of Organic Chemistry and Technology, Cracow University of Technology, 31155, Cracow, Poland


  • [1] R. Jasiński, Current Chem. Lett. 1, 157 (2012) http://dx.doi.org/10.5267/j.ccl.2012.8.001[Crossref]
  • [2] R. Huisgen, in: A. Padwa (Ed.), 1,3-Dipolar Cycloaddition Chemistry (Wiley Interscience, New York, 1984)
  • [3] P. Perez, L.R. Domingo, M.J. Aurell, R. Contreras, Tetrahedron 59, 3117 (2003) http://dx.doi.org/10.1016/S0040-4020(03)00374-0[Crossref]
  • [4] R. Jasiński, Tetrahedron, (in press), DOI: 10.1016/j.tet.2012.10.095 [Crossref]
  • [5] H. Wójtowicz-Rajchel, H. Koroniak, J. Fluor. Chem. 135, 225 (2012) http://dx.doi.org/10.1016/j.jfluchem.2011.11.005[Crossref]
  • [6] S. Krompiec, P. Bujak, J. Malarz, M. Krompiec, Ł. Skórka, T. Pluta, W. Danikiewicz, M. Kania, J. Kusz, Tetrahedron 68, 6018 (2012) http://dx.doi.org/10.1016/j.tet.2012.05.027[Crossref]
  • [7] R. Jasiński, M. Kwiatkowska, A. Barański, Wiad. Chem. 67, 485 (2007) and references cited therein
  • [8] R. Huisgen, P. Pöchlauer, G. Młostoń, K. Polsborn, Helv. Chim. Acta 90, 983 (2007) http://dx.doi.org/10.1002/hlca.200790102[Crossref]
  • [9] R. Huisgen, G. Młostoń, Modern Problem Org. Chem. 14, 23 (2004) and references cited therein
  • [10] G.A. Shvekhgeimer, A. Barański, M. Grzegożek, Synthesis 612 (1976)
  • [11] R. Jasiński, A. Ciężkowska, A. Lyubimcev, A. Barański, Chem. Heterocyclic Cmpd. 40, 206 (2004)
  • [12] R. Jasiński, K. Wąsik, M. Mikulska, A. Barański, J. Phys. Org. Chem. 22, 717 (2009) http://dx.doi.org/10.1002/poc.1505[Crossref]
  • [13] R. Jasiński, M. Mikulska, A. Barański, Slov. Chim. Acta 58, 41 (2011)
  • [14] A. Barański, R. Jasiński, E. Cholewka, In: Z. Kowalski (Ed.), Postępy w inżynierii i technologii chemicznej, (Cracow University of Technology, Cracow, 2011) (In Polish)
  • [15] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Jr. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, Y. Nakajima, O. Honda, O. Kitao, H. Nakai, M. Klene, X Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, M.C. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D. J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision B.04 (Gaussian, Inc., Pittsburgh PA, 2003)
  • [16] R.G. Parr, W. Yang, Density Functional Theory of Atoms and Molecules (Oxford University, New York, 1989)
  • [17] P. Perez, L.R. Domingo, A. Aizman and R. Contreras, In: A. Toro-Labbé (Ed.), Theoretical and Computational Chemistry (Elsevier, Amsterdam, 2007) vol. 19
  • [18] L.R. Domingo, E. Chamorro, P. Perez, J. Org. Chem. 73, 4615 (2008) http://dx.doi.org/10.1021/jo800572a[Crossref]
  • [19] G. Leroy, M. Sana, L.A. Burke, M.T. Nguyen, Quantum Theory Chem. React. 1. 91 (1980)
  • [20] M. Barone, M. Cossi, J. Tomasi, Geometry J. Comp. Chem. 19, 404 (1998) http://dx.doi.org/10.1002/(SICI)1096-987X(199803)19:4<404::AID-JCC3>3.0.CO;2-W[Crossref]
  • [21] L.R. Domingo, P. Perez, Org. Biomol. Chem. 9, (2011)
  • [22] A. Barański, Wiad. Chem. 54, 53 (2000)
  • [23] R. Jasiński, O. Koifman, A. Barański, Mendeleev Commun. 21, 262 (2011) http://dx.doi.org/10.1016/j.mencom.2011.09.010[Crossref]
  • [24] R. Jasiński, A. Barański, Polish J. Chem. 81, 1441 (2007)
  • [25] L.R. Domingo, M.J. Aurell, M. Arno, J.A. Saez, J. Mol. Struct. (Theochem) 811, 125 (2007) http://dx.doi.org/10.1016/j.theochem.2006.12.051[Crossref]

Document Type

Publication order reference


YADDA identifier

JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.