Structure Determination of Some Nitro-5,10,15,20-tetrakis(3-methoxyphenyl)porphyrins Using Simple NMR Techniques

• Autorzy: Ostrowski S. , Łopuszyńska B. , Mikus A.
• Konferencja: 1st Symp. on NMR in Chemistry, Biology and Medicine; 8-10 Semptember, Warsaw, Poland. Issue dedicated to honour Prof. Witanowski
• Języki publikacji: EN

Abstrakty

EN

The structures of some nitrosubstituted meso-tetraarylporphyrins were determined by a simple comparison of their 1H NMRspectra, and confirmed by NOE experiments. On the basis of these investigations it was found that in the meso-tetraphenylporphyrin (meso-TPP) and its 3-methoxy, 3-methyl, and 3-chloro-substituted derivatives (in the meso-aryl rings), the electrophilic nitration occurred in position 4-.

Słowa kluczowe

EN

meso-tetraarylporphyrins; nitration; 1H NMR; nuclear Overhauser effect; chemical shift increments

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2006
• Tom: Vol. 80, nr 7
• Strony: 1209--1215
• Opis fizyczny: Bibliogr. 16 poz., rys.

Twórcy

autor

Ostrowski S.

autor

Łopuszyńska B.

autor

Mikus A.

• Institute of Chemistry, University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland

Bibliografia

• 1.Kadish K.M., Smith K.M. and Guilard R., Eds.; In The Porphyrin Handbook, Academic Press: San Diego, CA, 2000; Vol. l and Vol. 13.
• 2.(a) Sternberg E.D., Dolphin D. and Bruckner Ch., Tetrahedron, 54, 4151 (1998); (b) Bourre L., Simonneaux G., Ferrand Y., Thibaut S., Lajat Y. and Patrice T., J. Photochem. Photobiol B, 69, 179 (2003); (c) Nyman E.S. and Hynninen P.H., J. Photochem. Photobiol. B, 73, l (2004).
• 3.Wei L., Padmaja K., Youngblood W.J., Lysenko A.B., Lindsey J.S. and Bocian D.F., J. Org. Chem., 69, 1461 (2004); and refs. cited therein.
• 4.(a) Imahori H., Hagiwara K., Aoki M., Akiyama T., Taniguchi S., Okada T., Shirakawa M. and Sakata Y, J. Am. Chem. Soc., 118,11771 (1996); (b) Cheng R, Wilson S.R. and Schuster D.I., Chem. Commun., 89 (1999); (c) Zheng G., Dougherty T.J. and Pandey R.K., Chem. Commun., 2469 (1999); (d) Lee J.-Ch., Kim T.-Y, Kang S.H. and Shim Y.K., Bull. Korean Chem. Soc., 22, 257 (2001); (e) Ostrowski S. and Mikus A., Mol. Divers., 6, 315 (2003).
• 5.Ruzie Ch., Gueyrard D. and Boitrel B., Tetrahedron Lett., 45, 1713 (2004); and refs. cited therein.
• 6.Kruper W.J., Jr., Chamberlin T.A. and Kochanny M., J. Org. Chem., 54,2753 (1989).
• 7.(a) Meng G.G., James B.R., Skov K.A. and Korbelik M., Canadian J. Chem., 72, 1894 (1994);(b) Matthews S.E., Pouton C.W. and Threadgill M.D., J. Chem. Soc., Chem. Commun., 1809 (1995);(c)  Faustino M.A.F., Neves M.G.P.M.S., Cavaleiro J.A.S., Neumann M., Brauer H.-D. and Jori G., Photochem. Photobiol, 72, 217 (2000).
• 8.(a) Ostrowski S. and Shim Y.K., Bull. Korean Chem. Soc., 22, 9 (2001); (b) Ostrowski S., Mikus A., Shim Y.K., Lee J.-Ch., Seo E.-Y., Lee K.-I. and Olejnik M., Heterocycles, 57,615 (2002).
• 9.Data from our laboratory (the spectrum was recorded in CDC^, 200 MHz); see also: Fuhrhop J.-H. and Smith K.M., In Porphyrins and Metalloporphyrins, Smith K.M., Ed.; Elsevier: Amsterdam, 1975, p. 413.
• 10.Günther H., NMR Spectroscopy. An Introduction, John Wiley & Sons, Chichester - New York, 1980,p. 104.
• 11.Clerc R and Simon S., In Tables of Spectral Data for Structure Determination of Organic Compounds', Boschke F.L., Fresenius W., Huber J.F.K., Pungor E., Rechnitz G.A., Simon W. and West Th.S., Eds.; Springer: Berlin, 1983, p. C120.
• 12.(a) Bookser B.C. and Bruice T.C., J. Am. Chem. Soc., 113, 4208 (1991); (b) Ref. (9), p. 442.
• 13.(a) Ostrowski S., Mikus A. and Borkowska A., Proceedings of 7th International Electronic Conference on Synthetic Organic Chemistry, Basel, Switzerland, A002 (2003); (b) Ostrowski S. and Mikus A., ibid.tA003 (2003).
• 14.Ostrowski S. and Łopuszyńska B., Synth. Commun., 33,4101 (2003).
• 15.(a) Rothemund R, J. Am. Chem. Soc., 58, 625 (1936); 63, 267 (1941); (b) Adler A.D., Longo F.R., Finarelli J.D., Goldmacher J., Assour J. and Korsakoff L., J. Org. Chem., 32, 476 (1967); (c) Lindsey J.S., Schreiman I.C., Hsu H.C., Kearney RC. and Marguerettaz A.M., J. Org. Chem., 52, 827 (1987).
• 16.Ostrowski S. and Mikus A., Heterocycles, 65, 2339 (2005).