1D AND 2D NMR STUDIES OF BENZYL O–VANILLIN

https://doi.org/10.22146/ijc.21598

Mohammed Hadi Al–Douh(1), Shafida Abd Hamid(2*), Hasnah Osman(3)

(1) School of Chemical Sciences, Universiti Sains Malaysia (USM), Minden 11800, Pinang
(2) School of Chemical Sciences, Universiti Sains Malaysia (USM), Minden 11800, Pinang
(3) School of Chemical Sciences, Universiti Sains Malaysia (USM), Minden 11800, Pinang
(*) Corresponding Author

Abstract


The reaction of o-vanillin A with benzyl bromide B2 in acetone as the solvent and K2CO3 as a base in the presence of tetra-n-butylammonium iodide (TBAI) as catalyst formed benzyl o-vanillin, C. The complete assignments of C using PROTON, APT, DEPT-135, COSY, NOESY, HMQC and HMBC NMR in both CDCl3 and acetone-d6 are discussed, and the coupling constants J are reported in Hertz (Hz).


Keywords


1H NMR; 13C NMR; 2D NMR; Benzyl o-Vanillin

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References

[1] McOmie, J.F.W., 1963, "Protective Groups" in Advance in Org. Chem. Method and Results. Eds. Raphael, R.A., Taylor E.C., and Wynberg, H., John Wiley and Sons, Inc., New York, Vol. 3, Ch. 4, 191–294.

[2] Feuer, H., and Hooz, J., 1967, "Methods of Formation of The Ether Linkage" in The Chemistry of the Ether Linkage. Ed. Patai, S., John Wiley and Sons, Inc., New York, Ch. 10, 446–498.

[3] Zaugg, R.H., Walder, J.A. and Klotz, I.M., 1977, J. Biol. Chem., 252, 23, 8542–8548.

[4] Magnus, P. and Sebhat, I.K., 1998, Tetrahedron, 54, 15509–15524.

[5] Scott, J.L. and Raston, C.L., 2000, Green Chem., 2, 245–247.

[6] Juhasz, L., Dinya, Z., Antus, S. and Gunda, T.E., 2000, Tetrahedron Lett., 41, 2491–2494.

[7] Baker, K., Marcus, C.B., Huffman, K., Kruk, H., Malfroy, B. and Doctrow, S.R., 1998, J. Pharm. Exp. Therap., 284, 215–221.

[8] Dessolin, J., Schuler, M., Quinart, A., Giorgi, F.D., Ghosez, L. and Ichas, F., 2002, Eur. J. Pharma., 447, 155–161.

[9] Hudlicky, T., Rinner, U., Gonzalez, D., Akgun, H., Schilling, S., Siengalewicz, P., Martinot, T.A. and Pettit, G.R., 2002, J. Org. Chem., 67, 8726–8743.

[10] Gonzalez, D., Martinot, T. and Hudlicky, T., 1999, Tetrahedron Lett., 40, 3077–3080.

[11] Smil, D.V., Laurent, A., Spassova, N.S. and Fallis, A.G., 2003, Tetrahedron Lett., 44, 5129–5132.

[12] Kim, E., Kim, J.Y. and Rhee, H., 2004, Bull. Korean Chem. Soc., 25, 1720–1722.

[13] Barik, A., Priyadarsini, K.I. and Mohan, H., 2004, Rad. Phy. Chem., 70, 687–696.

[14] Merz, K.W. and Fink, J., 1956, Arch. Pharm. Ber. dtsch. Pharm. Ges., 289, 347–358.

[15] Profft, E., 1957, J. Praks. Chem., 5, 175–181.

[16] Cotterill, A.S., Hartopp, P., Jones, G.B., Moody, C.J., Norton, C.L., O'Sullivan, N. and Swann, E., 1994, Tetrahedron, 50, 7857–7874.

[17] Krohn, K., Loock, U., Paavilainen, K., Hausen, B.M., Schmalle, H.W. and Kiesele, H., 2001, ARKIVOC, i, 88–130.

[18] Berger, J.M., 2001, "Isolation, Characterization, and Synthesis of Bioactive Natural Products from Rainforest Flora", Ph. D. Thesis, Virginia Polytechnic Institute and State University, Pennsylvania, USA.

[19] Lin, C.F., Yang, J.S., Chang, C.Y., Kuo, S.C., Lee, M.R. and Huang, L.J., 2005, Bioorg. Med. Chem., 13, 1537–1544.

[20] Al–Douh, M.H., Hamid, S.A., Osman, H., Ng, S.L. and Fun, H.K., 2006, Acta Cryst. E, 62, 10, o4767–o4770.

[21] Crystal data for C: C15H14O3, M = 242.26, monoclinic, space group P21/c, a = 13.7203(3), b = 4.6599(10), c = 19.1552(5) Ǻ, b = 97.736(1)°, V = 1213.55(5) Ǻ3, Z = 4, Dc = 1.326 g cm–3, m(Mo–Ka) = 0.092 mm–1, F(000) = 512, T = 297 K, 3905 independent reflections. Data were collected on Bruker SMART APEX2 CCD areadetector using w–scans [27], and the non–hydrogen atoms were refined anisotropically using full matrix least squares based on F2 to give R1 = 0.0514, wR2 = 0.1878 for 2949 independent observed reflections [F2 > 2s (F2), 2q = 31.2°] and 164 parameters. The structure was solved and refined by SHELXTL against F2 [28]. The software was used SHELXTL [28] and PLATON [29]. These data can be obtained free of charge from International Union of Crystallography IUCr ci2177 or The Cambridge Crystallographic Data Centre CCDC 627450. (Reference: doi:10.1107/S1600536806039250).

[22] Al–Douh, M.H., Hamid, S.A. and Osman, H., 2008, J. Nat. Appl. Sci., 12, 1, xxx–xxx. Accepted.

[23] Bruker program 1D WIN–NMR (release 6. 0) and 2D WIN–NMR (release 6.1).

[24] Berger, S. and Braun, S., 2004, 200 and More NMR Experiments, A Practical Course, Wiley–VCH, Weinheim.

[25] Al–Douh, M.H., Hamid, S.A. and Osman, H., 2008, J. Nat. Appl. Sci. Manuscript submmited.

[26] Balci, M., 2005, "Basic 1H– and 13C–NMR Spectroscopy", Elsevier, Ch. 4, 129–130.

[27] APEX2 (Version 1.27), SAINT (Version 7.12A), and SADABS (Version 2004/1), 2005, Bruker AXS Inc., Madison, Wisconsin, USA.

[28] Sheldrick, G.M., SHELXTL. (Version 5.1), 1998, Program for the Solution of Crystal Structures, Bruker AXS Inc., Madison, Wisconsin, USA.

[29] Spek, A.L., 2003, J. Appl. Crystallogr., 36, 7–13.



DOI: https://doi.org/10.22146/ijc.21598

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