1H NMR, 13C NMR and Computational Study of the Structure of Salicylaldehyde Anion in Solution

• Autorzy: Horbaczewski M. , Szczeciński P. , Gryff-Keller A. , Molchanov S.
• Języki publikacji: EN

Abstrakty

EN

1H NMR and 13C NMR spectra of salicylaldehyde potassium salt in DMF-d7 solution with addition of kryptofix 222 were mea sured. Quantitative comparison of car bon chemical shifts with shielding constants calculated for syn and anti con form ers of salicyl aldehyde an ion [GIAO DFT B3LYP/6-311G(2d,p) PCM] re vealed that in the applied conditions the anti form prevailed. Similar correla tion performed for salicylaldehyde lith ium salt indicated that in this case the syn conformer dominated. Analysis of experimental and calculated J(1H,13C) and J(1H,1H) values supported above conclusions.

Słowa kluczowe

EN

salicylaldehyde salts; NMR; DFT study

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 12
• Strony: 2089--2096
• Opis fizyczny: Bibliogr. 12 poz., rys.

Twórcy

autor

Horbaczewski M.

autor

Szczeciński P.

autor

Gryff-Keller A.

autor

Molchanov S.

• Faculty of Chemistry, Warsaw Unive sity of Technology, Noakowskiego 3, 00-664 Warszawa, Poland Fax: [phone],

Bibliografia

• 1. Mitchell G., Bartlett D. W., Fraser T.E.M., Hawkes T.R., Holt D.C., Towson J.K. and Wichert R.A., Pest. Manag. Sci., 57, 120 (2001).
• 2. Secor J., Plant Physiol, 106,1429 (1994).
• 3. (a) Linstedt S. and Holme E., Lancet, 340, 813 (1992); (b) Pronicka E., Rowińska E., Zawadzki J.,Holme E. and Linstedt S., J. Inherit. Metab. Dis., 19,234 (1996); (c) Lock E.A., Ellis M.K., Gaskin P.,Robinson M., Auton T.R., Provan W.M., Smith L.L., Prisbylla M.P., Mutter L.C. and Lee D.L., ibid. ,21,498 (1998); (d) Holme E. and Lindstedt S., ibid., 21, 507 (1998).
• 4. Kavana M. and Moran G.R., Biochemistry, 42,10238 (2003).
• 5. (a) Brownlee J.M., Johnson-Winters K., Harrison D.H.T. and Moran G.R., Biochemistry, 43, 6370 (2004); (b) Neidig M.L., Decker A., Kavana M., Moran G.R. and Solomon E.I., Biochem. Biophys. Res. Commun., 338, 206 (2005).
• 6. Szczeciński P., Gryff-Keller A. and Molchanov S., J. Org. Chem., 71, 4636 (2006).
• 7. Bugaj M. and Kamieńska-Trela K., Polish J. Chem., 80(7), 1217 (2006).
• 8.  Diez E., Casanueva J., San Fabian J., Esteban A.L., Galache M.P., Barone V., Peralta J.E. and Contreras R.H., Mol. Phys., 103(9), 1307 (2005).
• 9. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr.J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., FukudaR., Hasegawa J., Ishida M., Nakajima T, Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E.,Hratchian H.P., Cross J.B., Adamo C., J arami l lo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P.,Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K.,Rabuck A.D., Raghavachari K, Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi L, Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gili P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C. and Pople J.A., Gaussian 03, Revision B.05, Gaussian, Inc.: Pittsburgh, PA, 2003.
• 10. Tomasi J., Mennucci B. and Cammi R., Chem. Rev., 105,2999 (2005).
• 11. Mennucci B. and Tomasi J., J, Chem. Phys., 106, 5151 (2005).
• 12. Rappé A.K., Casewit C.J., Colwell K.S., Goddard III W.A. and Skiff W.M., J. Am. Chem. Soc., 114, 10024(1992).