1H and 13C NMR Spectra of Natural Products Laurene-Type Sesquiterpenes: Theoretical and Experimental Studies

Walied Mohamed Alarif; Mohamed Hassan Abdel-Rhman; Ahmed Abdel-Lateff; Sultan Samran Al-Lihaibi

doi:10.14233/ajchem.2014.17016

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Issue Published : September 16, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

1H and 13C NMR Spectra of Natural Products Laurene-Type Sesquiterpenes: Theoretical and Experimental Studies

https://doi.org/10.14233/ajchem.2014.17016

Walied Mohamed Alarif

Marine Chemistry Department, Faculty of Marine Sciences, King Abdulaziz University, Jeddah, Saudi Arabia; Permanent Address: Forensic Chemistry Laboratory at Mansoura, Ministry of Justice, Egypt

Mohamed Hassan Abdel-Rhman

Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt

Ahmed Abdel-Lateff

Natural Products and Alternative Medicine Department, Faculty of Pharmacy, King Abdulaziz University, Jeddah, Saudi Arabia; Permanent Address: Department of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia, Egypt

Sultan Samran Al-Lihaibi

Marine Chemistry Department, Faculty of Marine Sciences, King Abdulaziz University, Jeddah, Saudi Arabia

Corresponding Author(s) : Mohamed Hassan Abdel-Rhman

mhassan2371@yahoo.com

Asian Journal of Chemistry, Vol. 26 No. 19 (2014): Vol 26 Issue 19
Article Published : September 19, 2014

Abstract

Quantum chemical calculations for geometrical optimization of the natural products laurene-type sesquiterpenes, 12-hydroxy isolaurene (1), 8,11-dihydro-12-hydroxy isolaurene (2) and isolauraldehyde (3) isolated from the red alga Laurencia obtusa using density functional theory (DFT) were carried out. A comparable study between experimental ¹H and ¹³C NMR spectral data and calculated with DFT and ab initio Hartree-Fock (HF) methods were used to confirm the spectral data assignments of compounds 1-3. The calculated NMR spectral data showed good agreement with the experimental data supporting the obtained geometries. Among the studied methods, DFT/B3LYP method is most convenient one for prediction of ¹H and ¹³C NMR spectra of such compounds.

Keywords

Terpenoids Isolaurenes NMR spectroscopy DFT/B3LYP DFT/LSDA ab initio Calculation

Mohamed Alarif, W., Hassan Abdel-Rhman, M., Abdel-Lateff, A., & Samran Al-Lihaibi, S. (2014). 1H and 13C NMR Spectra of Natural Products Laurene-Type Sesquiterpenes: Theoretical and Experimental Studies. Asian Journal of Chemistry, 26(19), 6623–6629. https://doi.org/10.14233/ajchem.2014.17016

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References

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References

G.V.J. da Silva and A.C. Neto, Tetrahedron, 61, 7763 (2005); doi:10.1016/j.tet.2005.05.101.

E. Oldfield, Annu. Rev. Phys. Chem., 53, 349 (2002); doi:10.1146/annurev.physchem.53.082201.124235.

K. Wolinski, J.F. Hinton and P. Pulay, J. Am. Chem. Soc., 112, 8251 (1990); doi:10.1021/ja00179a005.

G. Barone, L. Gomez-Paloma, D. Duca, A. Silvestri, R. Riccio and G. Bifulco, Chem. Eur. J., 8, 3233 (2002); doi:10.1002/1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO;2-0.

R.C. Mawhinney and G. Schreckenbach, Magn. Reson. Chem., 42(S1), S88 (2004); doi:10.1002/mrc.1446.

P. Cimino, L. Gomez-Paloma, D. Duca, R. Riccio and G. Bifulco, Magn. Reson. Chem., 42(S1), S26 (2004); doi:10.1002/mrc.1410.

W.M. Alarif, S.S. Al-Lihaibi, S.N. Ayyad, M.H. Abdel-Rhman and F.A. Badria, Eur. J. Med. Chem., 55, 462 (2012); doi:10.1016/j.ejmech.2012.06.060.

M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr, T. 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, T. Nakajima, Y. 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, O. 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 and J.A. Pople, Gaussian 03W, Revision C.01, Gaussian Inc., Wallingford CT (2004).

R. Ditchfield, Mol. Phys., 27, 789 (1974); doi:10.1080/00268977400100711.

A.D. Becke, J. Chem. Phys., 98, 5648 (1993); doi:10.1063/1.464913.

C. Lee, W. Yang and R.G. Parr, Phys. Rev. B, 37, 785 (1988); doi:10.1103/PhysRevB.37.785.

J.P. Perdew and Y. Wang, Phys. Rev. B, 45, 13244 (1992); doi:10.1103/PhysRevB.45.13244.

R.G. Parr and W. Yang, Density-Functional Theory of Atoms and Mole-cules, Oxford University Press (1989).

S. Sadhukhan, D. Muñoz, C. Adamo and G.E. Scuseria, Chem. Phys. Lett., 306, 83 (1999); doi:10.1016/S0009-2614(99)00442-X.

I.S. Lim and G.E. Scuseria, Chem. Phys. Lett., 460, 137 (2008); doi:10.1016/j.cplett.2008.06.008.

T. Cai, H. Han, Y. Yu, T. Gao, J. Du and L. Hao, J. Phys. B, 404, 89 (2009); doi:10.1016/j.physb.2008.10.009.

R.D. Dennington, T.A. Keith and J.M. Millam, GaussView 5, Gaussian Inc., Wallingford CT (2008).

J.A. Gascon, E.M. Sproviero and V.S. Batista, J. Chem. Theory Comput., 1, 674 (2005); doi:10.1021/ct0500850.

A.E. Aliev, D. Courtier-Murias and S. Zhou, J. Mol. Struct. (THEO), 893, 1 (2009); doi:10.1016/j.theochem.2008.09.021.

F.L.P. Costa, A.C.F. de Albuquerque, F.M. dos SantosJr. and M.B. de Amorim, J. Phys. Org. Chem., 23, 972 (2010); doi:10.1002/poc.1749.

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

1H and 13C NMR Spectra of Natural Products Laurene-Type Sesquiterpenes: Theoretical and Experimental Studies

Corresponding Author(s) : Mohamed Hassan Abdel-Rhman

Abstract

Keywords

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