Copyright (c) 2013 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Theoretical Determination of Structures of Terpenoids 18a-Oleanane and A-Neo-18a-oleanene
Corresponding Author(s) : A. Cheriti
Asian Journal of Chemistry,
Vol. 25 No. 7 (2013): Vol 25 Issue 7
Abstract
The purpose of this study was to determine which of the quantum chemistry methods PM3, HF and DFT/B3LYP evaluate more accurately the geometric parameters of two terpenoids 18a-oleanane (1) and A-neo-18a-oleanene (2). The theoretical results were compared to experimental data generated by X-ray diffraction. Compound 1, C32H52O3, crystallizes in space group C2 with a = 13.3520 (2), b = 6.54000 (10), c = 32.4439(5) Å,V = 2798.13(7) Å3 and Z = 4. The structure was refined to a final R = 0.027 for the structure factors observed with I ³ 3s(I). The second molecule 2, C30H46O2, crystallizes in the monoclinic space group with a = 13.2214 (4), b = 6.4962 (2), c = 29.8420(9) Å,V = 2558.00(13) Å3 and Z = 4. The structure was refined to a final R = 0.061 for the structure factors observed with I = 2s(I). A comparative study using ab initio calculation (HF/6-31G**), semi empirique (PM3) and DFT(B3LYP/6-31G**) shows a high correlation with the geometric data of X-ray diffraction. The difference between the calculated and experimental values is very insignificant.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- (a) J.W.H. Li and J.C. Vederas, Science, 325, 161 (2009); (b) E. Pichersky, J.P. Noel and N. Dudareva, Science, 311, 808 (2006); (c) S.A. Goff and H.J. Klee, Science, 311, 815 (2006).
- I.D. Connolly and R.A. Hill, Dictionary of Terpenoids, Chapman and Hall, London, 2 (1991).
- S. Charles, A Fragrant Introduction to Terpenoid, RCS, London (2003).
- J.A.R. Salvador, R.M.A. Pinto, R.C. Santos, C. Le Roux, A.M. Beja and J.A. Paixão, Org. Biomol. Chem., 7, 508 (2009).
- C. Seger, S. Pointinger and H. Greger, Phytochemistry, 69, 2696 (2008).
- E. Sievänen, A. Valkonen, M. Lahtinen and M. Tolonen, J. Mol. Struct., 979, 172 (2010).
- M.I.C. Choudhary, M.Z. Iqbal, A.U. Rahman, A.M. Khan, A. Farooq, B. Demirci,A. Canbas and K.H. Baser, Chem. Nat. Comp., 41, 4 (2005).
- M.C. Etter, Z. Urbanczyk-Lipowska, S. Baer and P.F. Barbara, J. Mol. Struct., 144, 155 (1986).
- A. Cheriti,A. Babadjamian and G. Balansard, J. Nat. Prod., 57, 8 (1994).
- N. Belboukhari and A. Cheriti, Chem. Nat. Comp., 45, 5 (2009).
- (a) N. Belboukhari, A. Cheriti, C. Roussel and N. Vanthuyne, Nat. Prod. Res., 24, 7 (2010); (b) H. Djeradi, A. Rahmouni and A. Cheriti, Phys. Chem. Indian J., 6, 63 (2011).
- M.J.S. Dewar, E.G. Zoebish, E.F. Healy and J.J.P. Stewart, J. Am. Chem. Soc., 107, 13 (1985).
- J.S. Binkley, J.A. Pope and W.J. Hehre, J. Am. Chem. Soc., 102, 939 (1980).
- R.G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford and New York (1989).
- (a) A.D. Becke, J. Chem. Phys., 98, 5648 (1993); (b) C. Lee, W. Yang and R.G. Parr, Phys. Rev. B, 37, 785 (1988).
- F.J.L. Santos, A.F.C. Alcântara and D. Piló-Veloso, Struct. Chem., 19, 625 (2008).
- A.F.C. Alcântara, D. Piló-Veloso, W.B. Almeira, C.R.A. Maltha and L.C.A. Barbosa, J. Mol. Struct., 791, 180 (2006).
- A. Pérez-Rebolledo, I.C. Mendes, N.L. Speziali, P. Bertani, J.M. Resende, A.F. de Carvalho Alcântara and H. Beraldo, Polyhedron, 26, 1449 (2007).
- M.J. Frisch et al., J.A. Gaussian 98, Revision A.9, Gaussian, Inc., Pittsburgh, PA (1998).
- A.C.G. Marigliano and E.L. Varetti, J. Phys. Chem. A, 106, 1100 (2002).
- F. Sim, A.S. Amant, I. Papai and D.R. Salahub, J. Am. Chem. Soc., 114, 4391 (1992).
References
(a) J.W.H. Li and J.C. Vederas, Science, 325, 161 (2009); (b) E. Pichersky, J.P. Noel and N. Dudareva, Science, 311, 808 (2006); (c) S.A. Goff and H.J. Klee, Science, 311, 815 (2006).
I.D. Connolly and R.A. Hill, Dictionary of Terpenoids, Chapman and Hall, London, 2 (1991).
S. Charles, A Fragrant Introduction to Terpenoid, RCS, London (2003).
J.A.R. Salvador, R.M.A. Pinto, R.C. Santos, C. Le Roux, A.M. Beja and J.A. Paixão, Org. Biomol. Chem., 7, 508 (2009).
C. Seger, S. Pointinger and H. Greger, Phytochemistry, 69, 2696 (2008).
E. Sievänen, A. Valkonen, M. Lahtinen and M. Tolonen, J. Mol. Struct., 979, 172 (2010).
M.I.C. Choudhary, M.Z. Iqbal, A.U. Rahman, A.M. Khan, A. Farooq, B. Demirci,A. Canbas and K.H. Baser, Chem. Nat. Comp., 41, 4 (2005).
M.C. Etter, Z. Urbanczyk-Lipowska, S. Baer and P.F. Barbara, J. Mol. Struct., 144, 155 (1986).
A. Cheriti,A. Babadjamian and G. Balansard, J. Nat. Prod., 57, 8 (1994).
N. Belboukhari and A. Cheriti, Chem. Nat. Comp., 45, 5 (2009).
(a) N. Belboukhari, A. Cheriti, C. Roussel and N. Vanthuyne, Nat. Prod. Res., 24, 7 (2010); (b) H. Djeradi, A. Rahmouni and A. Cheriti, Phys. Chem. Indian J., 6, 63 (2011).
M.J.S. Dewar, E.G. Zoebish, E.F. Healy and J.J.P. Stewart, J. Am. Chem. Soc., 107, 13 (1985).
J.S. Binkley, J.A. Pope and W.J. Hehre, J. Am. Chem. Soc., 102, 939 (1980).
R.G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford and New York (1989).
(a) A.D. Becke, J. Chem. Phys., 98, 5648 (1993); (b) C. Lee, W. Yang and R.G. Parr, Phys. Rev. B, 37, 785 (1988).
F.J.L. Santos, A.F.C. Alcântara and D. Piló-Veloso, Struct. Chem., 19, 625 (2008).
A.F.C. Alcântara, D. Piló-Veloso, W.B. Almeira, C.R.A. Maltha and L.C.A. Barbosa, J. Mol. Struct., 791, 180 (2006).
A. Pérez-Rebolledo, I.C. Mendes, N.L. Speziali, P. Bertani, J.M. Resende, A.F. de Carvalho Alcântara and H. Beraldo, Polyhedron, 26, 1449 (2007).
M.J. Frisch et al., J.A. Gaussian 98, Revision A.9, Gaussian, Inc., Pittsburgh, PA (1998).
A.C.G. Marigliano and E.L. Varetti, J. Phys. Chem. A, 106, 1100 (2002).
F. Sim, A.S. Amant, I. Papai and D.R. Salahub, J. Am. Chem. Soc., 114, 4391 (1992).