Probing the molecular and electronic structure of the lichen metabolite usnic acid: A DFT study

Chemical Physics

Volumn 374, Issue 1-3, 2010, Pages 138-145

  Galasso, V ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

Author keywords

Absorption spectrum; DFT calculations; NMR chemical shifts; Structure; Vibrational frequencies

Indexed keywords

EID: 77955923976     PISSN: 03010104     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphys.2010.07.017     Document Type: Article

References (68)

1. S. Huneck, and Y. Yoshimura Identification of Lichen Substances 1996 Springer-Verlag Berlin
2. K. Ingólfsdóttir Phytochemistry 61 2002 729
3. M. Cocchietto, N. Skert, P.L. Nimis, and G. Sava Naturwissenschaften 89 2002 137
4. A.A. Al-Robai, and D.A. Al-Jawhari Nat. Toxins 4 1996 96
5. I. Francolini, P. Norris, A. Piozzi, G. Donelli, and P. Stoodley Antimicrob. Agents Chemother. 48 2004 4360
6. J.W. Bierke, D. Gwynn-Jones, and T.V. Callaghan Environ. Exp. Bot. 53 2005 139
7. R. Nybakken, and R. Julkunen-Tiitto Lichenologist 38 2006 477
8. A. Fournet, M.E. Ferreire, A.R. Arias, S.T. Ortiz, A. Inchausti, and G. Yaluff Comp. Biochem. Physiol. 116 1997 51
9. K. Ingólfsdóttir, G.A.C. Chung, V.G. Skuúlason, S.R. Gissurarson, and M. Vilhelmsdóttir Eur. J. Pharm. Sci. 6 1998 141
10. C.S. Vijayakumara, S. Viswanathana, U.M. Kannappa, S. Reddya, A.B. Parvathavarthinia, and E. Sukumarb Fitoterapia 71 2000 564
11. R.M. Ribeiro-Costa, A.J. Alves, N.P. Santos, S.C. Nascimento, E.C.P. Gonalves, N.H. Silva, N.K. Honda, and N.S. Santos-Magalhäes J. Microencapsulation 21 2004 371
12. N.P.S. Santos, S.C. Nascimento, M.S.O. Wanderley, N.T. Pontes-Filho, J.F. Silva, and C.M. Castro J. Pharm. Biopharm. 64 2006 154
13. L. Guo, Q. Hi, J.-L. Fang, N. Mei, A.A. Ali, S.M. Lewis, and J.E.A. Leakley J. Environ. Sci. Health C 26 2008 317
14. R. Norrestam, M. von Glehn, and C.A. Wachtmeister Acta Chem. Scand. B 28 1974 1149
15. U. Behrens, G. Hencken, and J. Kopf Cryst. Struct. Commun. 5 1976 51
16. F.R. Fronczek, N.H. Fischer, Cambridge Crystallographic Data Centre, Deposition Number 297381, 2006.
17. K. Osterrothová, and J. Jehlika Spectrochim. Acta A 73 2009 576
18. H.G.M. Edwards, E.M. Newton, and D.D. Wynn-Williams J. Mol. Struct. 651-653 2003 27
19. A.D. Becke J. Chem. Phys. 98 1993 5648
20. E.B. Wilson, J.C. Decius, and P.C. Cross Molecular Vibrations 1945 McGraw-Hill New York
21. G. Rauhut, and P. Pulay J. Phys. Chem. 99 1995 3093
22. T.A. Keith, and R.F.W. Bader Chem. Phys. Lett. 210 1993 223
23. R.E. Stratmann, G.E. Scuseria, and M.J. Frisch J. Chem. Phys. 109 1998 8218
24. J. Tomasi, B. Mennucci, and R. Cammi Chem. Rev. 105 2005 2999
25. M.J. Frisch et al., GAUSSIAN'03, Revision D.01, Gaussian Inc., Wallingford, CT, 2004.
26. C. Peng, P.Y. Ayala, H.B. Schlegel, and M.J. Frisch J. Comput. Chem. 17 1996 49
27. C. Peng, and H.B. Schlegel Israel J. Chem. 33 1994 449
28. G. Buemi, and F. Zuccarello J. Mol. Struct. THEOCHEM 209 1990 89
29. E.R. Correché, M. Carrasco, M.E. Escudero, L. Velázquez, A.M.S. de Guzmán, F. Giannini, R.D. Enriz, E.A. Jáuregui, J.P. Ceñal, and O.S. Giordano Fitoterapia 69 1998 493
30. G.A. Jeffrey, and W. Saenger Hydrogen Bonding in Biological Structures 1991 Springer-Verlag Berlin
31. M. Garcia-Viloca, A.G. Lafont, and J.M. Lluch J. Am. Chem. Soc. 118 1997 1081
32. B. Schiøtt, B.B. Iversen, G.K.H. Madsen, and T.C. Bruice J. Am. Chem. Soc. 120 1998 12117
33. R.F.W. Bader Atoms in Molecules: A Quantum Theory 1990 Clarendon Press Oxford
34. E. Espinosa, E. Molins, and C. Lecomte Chem. Phys. Lett. 285 1998 170
35. S. Jenkins, and I. Morrison Chem. Phys. Lett. 317 2000 97
36. R.K. Sharma, and P. Jannke J. Indian J. Chem. 4 1966 16
37. M.J. Frisch et al., GAUSSIAN'98, Revision A.6, Gaussian Inc., Pittsburgh, PA, 1998.
38. J. Tomasi, and M. Persico Chem. Rev. 94 1994 2027
39. C. Cramer, and D.G. Truhlar Chem. Rev. 99 1999 2161
40. M. Orozco, and F.J. Luque Chem. Rev. 100 2000 4187
41. N. Rega, G. Scalmani, and V. Barone J. Comput. Chem. 24 2003 669
42. M. Suci, and M. Jing J. Phys. Chem. B 111 2007 4128
43. Z. Rappoport CRC Handbook of Tables for Organic Compound Identification 1967 The Chemical Rubber Co. Cleveland, OH
44. O.S. Wolfbeis Zeit. Phys. Chem. N.F. 125 1981 15
45. H. Terada Chem. Pharma. Bull. 20 1972 765
46. D.K. Palit, T. Mukherjee, and J.P. Mittal J. Indian Chem. Soc. 63 1986 35
47. M. Hauck, and S.-R. Jürgens Environ. Pollut. 156 2008 115
48. N. Valencia-Islas, A. Zambrano, and J.L. Rojas J. Chem. Ecol. 33 2007 1619
49. J.S. Wright, E.R. Johnson, and G.A. DiLabio J. Am. Chem. Soc. 123 2001 1173
50. H.-Y. Zhang, Y.-M. Sun, and X.-L. Wang J. Org. Chem. 67 2002 2709
51. J. Overend, and J.R. Scherer J. Chem. Phys. 32 1960 1289
52. M.V. Vener, and S. Scheiner J. Phys. Chem. 99 1995 642
53. H. Lee, and J.K. Wilmshurst Aust. J. Chem. 19 1966 1529
54. T. Meikle, and R. Stevens J. Chem. Soc., Perkin I 1978 1303
55. G.M. König, and A.D. Wright Phytochem. Anal. 10 1999 279
56. G.E. Langford, H. Auski, J.A. Gosbee, F.N. MacLachlan, and P. Yates Tetrahedron 37 1981 1091
57. B.F. Bowden, D.W. Cameron, M.J. Crossley, G.J. Feutrill, P.J. Griffiths, and D.P. Kelly Aust. J. Chem. 32 1979 769
58. P. Äyräs, S. Lötjönen, and C.-J. Widén Planta Med. 42 1981 187
59. H. Lampert, W. Mikenda, A. Karpfen, and J. Kählig J. Phys. Chem. A 110 1997 9610
60. T.J. Lillie, and O.C. Musgrave J. Chem. Soc., Perkin I 1977 355
61. M. McEvoy, L. Nybakken, K.A. Solhaug, and Y. Gauslaa Mycol. Prog. 5 2006 221
62. C. Reichardt Chem. Rev. 94 1994 2319
63. N.S. Hush, and J.R. Reimers Chem. Rev. 100 2000 775
64. M. Suci, and M. Jing J. Phys. Chem. B 112 2008 4313
65. E.E. Barnes, and W.T. Simpson J. Chem. Phys. 39 1963 670
66. S. Bell, T.L. Ng, and A.D. Walsh J. Chem. Soc., Faraday Trans. II 1975 393
67. F.R. Conde, M.S. Churio, and C.M. Previtali Photochem. Photobiol. Sci. 3 2004 960
68. E. Schultz, E. Samoylova, W. Radloff, I.V. Hertel, A.L. Sobolewski, and W. Domcke Science 306 2004 1765