DFT Evaluation of Reactivity of -Substituted meso-Bromoporphyrins towards Nucleophilic Substitution

Kirill P. Birin,^a@ Yulia G. Gorbunova,^a,b and Aslan Yu. Tsivadze^a,b

Dedicated to Full member of RAS Irina P. Beletskaya on occasion of her Anniversary

^aA.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS, 119071 Moscow, Russia

^bN.S. Kurnakov Institute of General and Inorganic Chemistry RAS, 119991 Moscow, Russia

^@Corresponding author E-mail: kirill.birin@gmail.com

DOI: 10.6060/mhc180280b

Macroheterocycles 2018 11(2) 150-154

The electronic structure of 15 model 5-bromoporphyrins was investigated by means of DFT B3LYP method. The comparison of the relative energy and the frontier molecular orbitals localization allowed the elucidation of the influence of the β-substituents electronic origin onto the electronic structure of the molecule. The obtained data is valuable for the evaluation of the relative reactivity of the 5-bromoporphyrins in the nucleophilic substitution reactions.

References:

Click here to expand or collapse this section

1. Alonso C.M.A., Barata J.F.B., Cavaleiro J.A.S., Faustino M.A.F., Monti D., Nardis S., Neves M.G.P.M.S., Pires S.M.G., Santos C.I.M., Smith K.M., Tome A.C., Serra V.I.V., Wojaczynski J. In: Synthesis and Modifications of Porphyrinoids (Paolesse R., Ed.) Springer Berlin Heidelberg, 2014. p. 1–301.

2. Beletskaya I.P., Tyurin V.S., Uglov A., Stern C., Guilard R. In: Handbook of Porphyrin Science (Guilard R., Kadish K.M., Smith K.M., Eds.) World Scientific Publishing, 2012. p. 81–279.

3. Senge M.O., Bischoff I. Tetrahedron Lett. 2004, 45, 1647–1650.
https://doi.org/10.1016/j.tetlet.2003.12.121

4. Senge M.O. Acc. Chem. Res. 2005, 38, 733–743.
https://doi.org/10.1021/ar0500012

5. Crossley M.J., King L.G. J. Chem. Soc., Perkin Trans. 1 1996, 1251.
https://doi.org/10.1039/p19960001251

6. Kalisch W.W., Senge M.O. Angew. Chem. Int. Ed. 1998, 37, 1107–1109.
https://doi.org/10.1002/(SICI)1521-3773(19980504)37:8<1107::AID-ANIE1107>3.0.CO;2-Z

7. Senge M.O., Kalisch W.W., Bischoff I. Chem. Eur. J. 2000, 6, 2721–2738.
https://doi.org/10.1002/1521-3765(20000804)6:15<2721::AID-CHEM2721>3.0.CO;2-Z

8. Feng X., Senge M.O. Tetrahedron 2000, 56, 587–590.
https://doi.org/10.1016/S0040-4020(99)01055-8

9. Feng X., Senge M.O. J. Chem. Soc., Perkin Trans. 1 2001, 1030–1038.
https://doi.org/10.1039/b100012h

10. Senge M.O., Hatscher S.S., Wiehe A., Dahms K., Kelling A. J. Am. Chem. Soc. 2004, 126, 13634–13635.
https://doi.org/10.1021/ja045223u

11. Fazekas M., Pintea M., Senge M.O., Zawadzka M. Tetrahedron Lett. 2008, 49, 2236–2239.
https://doi.org/10.1016/j.tetlet.2008.02.029

12. Ryan A.A., Plunkett S., Casey A., McCabe T., Senge M.O. Chem. Commun. 2014, 50, 353–355.
https://doi.org/10.1039/C3CC46828C

13. Crossley M.J., King L.G., Simpson J.L. J. Chem. Soc., Perkin Trans. 1 1997, 4, 3087–3096.
https://doi.org/10.1039/a701673e

14. Crossley M.J., King L.G., Pyke S.M., Tansey C.W. J. Porphyrins Phthalocyanines 2002, 6, 685–694.
https://doi.org/10.1142/S1088424602000816

15. Balaban M.C., Eichhöfer A., Buth G., Hauschild R., Szmytkowski J., Kalt H., Balaban T.S. J. Phys. Chem. B 2008, 112, 5512–5521.
https://doi.org/10.1021/jp801510b

16. Balaban M.C., Chappaz-Gillot C., Canard G., Fuhr O., Roussel C., Balaban T.S. Tetrahedron 2009, 65, 3733–3739.
https://doi.org/10.1016/j.tet.2009.02.039

17. Ostrowski S., Grzyb S. Tetrahedron Lett. 2012, 53, 6355–6357.
https://doi.org/10.1016/j.tetlet.2012.09.024

18. Grzyb S., Ostrowski S. Jordan J. Chem. 2012, 7, 231–237.

19. Devillers C.H., Hebié S., Lucas D., Cattey H., Clément S., Richeter S. J. Org. Chem. 2014, 79, 6424–6434.
https://doi.org/10.1021/jo5005586

20. Chen Q., Zhu Y., Fan Q., Zhang S., Zheng J. Org. Lett. 2014, 16, 1590–1593.
https://doi.org/10.1021/ol500191j

21. Chappaz-Gillot C., Canard G., Andreoli F., Vanthuyne N., Giorgi M., Naubron J.-V., Monnier V., Rosas R., Roussel C., Balaban T.S. Eur. J. Org. Chem. 2012, 2012(33), 6526–6536.
https://doi.org/10.1002/ejoc.201200985

22. Yamashita K., Kataoka K., Asano M.S., Sugiura K. Org. Lett. 2012, 14, 190–193.
https://doi.org/10.1021/ol202973z

23. Birin K.P., Gorbunova Y.G., Tsivadze A.Y., Bessmertnykh-Lemeune A.G., Guilard R. Macroheterocycles 2012, 5, 338–342.
https://doi.org/10.6060/mhc2012.121101b

24. Bruhn T., Witterauf F., Götz D.C.G., Grimmer C.T., Würtemberger M., Radius U., Bringmann G. Chem. Eur. J. 2014, 20, 3998–4006.
https://doi.org/10.1002/chem.201304169

25. Michalak J., Birin K.P., Muniappan S., Ranyuk E., Enakieva Y.Y., Gorbunova Y.G., Stern C., Bessmertnykh-Lemeune A., Guilard R. J. Porphyrins Phthalocyanines 2014, 18, 35–48.
https://doi.org/10.1142/S1088424614500084

26. Birin K.P., Gorbunova Y.G., Tsivadze A.Y., Bessmertnykh-Lemeune A.G., Guilard R. Eur. J. Org. Chem. 2015, 2015(25), 5610–5619.
https://doi.org/10.1002/ejoc.201500628

27. Abdulaeva I.A., Birin K.P., Michalak J., Romieu A., Stern C., Bessmertnykh-Lemeune A., Guilard R., Gorbunova Y.G., Tsivadze A.Y. New J. Chem. 2016, 40, 5758–5774.
https://doi.org/10.1039/C5NJ03247D

28. Birin K.P., Gorbunova Y.G., Tsivadze A.Y. RSC Adv. 2015, 5, 67242–67246.
https://doi.org/10.1039/C5RA13532J

29. Birin K.P., Poddubnaya A.I., Abdulaeva I.A., Gorbunova Y.G., Tsivadze A.Y. Dye. Pigm. 2018, in press.

Attachment	Size
mhc180280b.pdf	1.23 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

DFT Evaluation of Reactivity of -Substituted meso-Bromoporphyrins towards Nucleophilic Substitution

References: