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2010 | 8 | 4 | 928-936
Tytuł artykułu

An ab initio simulation of the UV/Visible spectra of substituted chalcones

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The electronic absorption spectra of 29 phenyl-ring substituted chalcones have been investigated with the time-dependent density functional theory (TD-DFT) and polarizable continuum TD-DFT (PCM-TD-DFT). It turns out that the hybrid PBE1PBE functional with the 6-31G basis set provide reliable λmax when the solvent effects are included in the model. Comparisons with experimental values lead to a mean absolute error of 12 nm (0.136 eV). Moreover, the observed substituent effects are reproduced by calculation qualitatively. The λmax of substituted chalcone in phenyl ring A is less sensitive to substitution than that in ring B. The linear correlation of Hammett’s substituent constants (σP) with LUMO energies is better with respect to HOMO energies. The calculation reveals that the maximum absorption band mainly results from the π→π* transition from HOMO to LUMO. The analysis of the electron density plots of frontier molecular orbitals show that most transitions should be of valence excitation nature. [...]
Słowa kluczowe
Wydawca

Czasopismo
Rocznik
Tom
8
Numer
4
Strony
928-936
Opis fizyczny
Daty
wydano
2010-08-01
online
2010-06-17
Twórcy
autor
  • Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China, xzmcysxue@sina.com
autor
  • Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China
autor
  • Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China
autor
  • Department of Chemistry, Nanjing University of Science and Technology, Nanjing, 210094, China
autor
  • Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China
autor
  • Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China
Bibliografia
  • [1] S. Murakami, M. Muramatsu, H. Aihara, Biochem. Pharmacol. 42, 1447 (1991) http://dx.doi.org/10.1016/0006-2952(91)90458-H[Crossref]
  • [2] R.J. Anto, et al., Cancer Lett. 97, 33 (1995) http://dx.doi.org/10.1016/0304-3835(95)03945-S[Crossref]
  • [3] N.J. Lawrence, A.T. McGown, Curr. Pharm. Design, 11, 1679 (2005) http://dx.doi.org/10.2174/1381612053764733[Crossref]
  • [4] Z. Nowakowska, Eur. J. Med. Chem. 42, 125 (2007) http://dx.doi.org/10.1016/j.ejmech.2006.09.019[Crossref]
  • [5] M. Liu, P. Wilairat, M.L. Go, J. Med. Chem. 44, 4443 (2001) http://dx.doi.org/10.1021/jm0101747[Crossref]
  • [6] D. Batovska, Eur. J. Med. Chem. 42, 87 (2007) http://dx.doi.org/10.1016/j.ejmech.2006.08.012[Crossref]
  • [7] J.H. Wu, X.H. Wang, Y.H. Yi, Bioorg. Med. Chem. Lett. 13, 1813 (2003) http://dx.doi.org/10.1016/S0960-894X(03)00197-5[Crossref]
  • [8] L. Mathiesen, K.E. Malterud, R.B. Sund, Planta Med. 61, 515 (1995) http://dx.doi.org/10.1055/s-2006-959360[Crossref]
  • [9] M.P. Cockerham, C.C. Frazier, S. Guha, E.A. Chauchard, Appl. Phys. B53, 275 (1991).
  • [10] B.K. Sarojinia, B. Narayanab, B.V. Ashalathab, J. Indirac, K.G. Lobo, J. Cryst. Growth 295, 54 (2006) http://dx.doi.org/10.1016/j.jcrysgro.2006.07.013[Crossref]
  • [11] H.J. Ravindra, K. Chandrashekaran, W.T.A. Harrison, S.M. Dharmaprakash, Appl. Phys. B94, 503 (2009)
  • [12] P. Poornesh, et al., Opt. Mater. 31, 854 (2009) http://dx.doi.org/10.1016/j.optmat.2008.09.007[Crossref]
  • [13] S. Shettigar, K. Chandrasekharan, G. Umesh, B.K. Sarojini, B. Narayana, Polymer 47, 3565 (2006) http://dx.doi.org/10.1016/j.polymer.2006.03.062[Crossref]
  • [14] P.S. Patila, et al., J. Cryst. Growth 303, 520 (2007) http://dx.doi.org/10.1016/j.jcrysgro.2006.12.068[Crossref]
  • [15] P.S. Patila, S.M. Dharmaprakasha, H.K. Funb, M.S. Karthikeyan, J. Cryst. Growth 297, 111 (2006) http://dx.doi.org/10.1016/j.jcrysgro.2006.09.017[Crossref]
  • [16] A.A. Sukhorukov, B.A. Zadorozhnyi, V.F. Lavrushin, Theor. Exp. Chem. 6, 490 (1973) http://dx.doi.org/10.1007/BF00530061[Crossref]
  • [17] M. Reinkhardt, A.A. Sukhorukov, A. Raushal, V.F. Lavrushin, Chem. Heterocyclic. Comp. 13, 969 (1977) http://dx.doi.org/10.1007/BF00472448[Crossref]
  • [18] V.G. Mitina, A.O. Doroshenko, A.A. Sukhorukov, V.F. Lavrushin, Theor. Exp. Chem. 20, 141 (1984) http://dx.doi.org/10.1007/BF00592798[Crossref]
  • [19] V.L. Gineitite, G.A. Gasperavichene, Theor. Exp. Chem. 25, 247(1989) http://dx.doi.org/10.1007/BF01298999[Crossref]
  • [20] K. Ohno, Y. Itoh, T. Harnada, M. Isogai, A. Kakuta, Mol. Cryst. Liq. Cryst. A182, 17 (1990) http://dx.doi.org/10.1080/00268949008047784[Crossref]
  • [21] K. Gustav, R. Colditz, A. Jabs, J. Prakt. Chem. 332, 645 (1990) http://dx.doi.org/10.1002/prac.19903320509[Crossref]
  • [22] M. Oumi, D. Maurice, M.H. Gordon, Spectrochim. Acta A55, 525 (1999)
  • [23] K.S. David, et al., J. Am. Chem. Soc. 128, 12243 (2006) http://dx.doi.org/10.1021/ja063586j[Crossref]
  • [24] I. Ciofini, P.P. Lainé, F. Bedioui, C. Adamo, J. Am. Chem. Soc. 126, 10763 (2004) http://dx.doi.org/10.1021/ja0482278[Crossref]
  • [25] D. Jacquemin, et al., J. Chem. Phys. 121, 1736 (2004) http://dx.doi.org/10.1063/1.1764497[Crossref]
  • [26] D. Jacquemin, J. Preat, V. Wathelet, M. Fontaine, E.A. Perpete, J. Am. Chem. Soc. 128, 2072 (2006) http://dx.doi.org/10.1021/ja056676h[Crossref]
  • [27] B.B. Koleva, T. Kolev, R. Nikolova, Y. Zagraniarsky, M. Spiteller, Cent. Eur. J. Chem. 6, 592 (2008 http://dx.doi.org/10.2478/s11532-008-0061-0[Crossref]
  • [28] D. Jacquemin, E.A. Perpte, I. Ciofini, C. Adamo, Acc. Chem. Res. 42, 326 (2009) http://dx.doi.org/10.1021/ar800163d[Crossref]
  • [29] N. Santhanamoorthi, K. Senthilkumar, P. Kolandaivel, Mol. Phys. 107, 1629 (2009) http://dx.doi.org/10.1080/00268970902997858[Crossref]
  • [30] Z.W. Qu, H. Zhu, V. May, J. Phys. Chem. B113, 4817 (2009)
  • [31] S. Lunak Jr. et al., Dyes Pigments 85, 27 (2010) http://dx.doi.org/10.1016/j.dyepig.2009.09.014[Crossref]
  • [32] I.F. Janczareka et al., Spectrochim. Acta A72, 394 (2009)
  • [33] A. Amat, C. Clementi, F. De Angelis, A. Sgamellotti, S. Fantacci, J. Phys. Chem. A113, 15118 (2009)
  • [34] L. Serrano-Andres, M. Merchan, J. Mol. Struct. (Theochem.) 729, 99 (2005) http://dx.doi.org/10.1016/j.theochem.2005.03.020[Crossref]
  • [35] Y.S. Xue, X.D. Gong, J. Mol. Struct. (Theochem.) 901, 226 (2009) http://dx.doi.org/10.1016/j.theochem.2009.01.034[Crossref]
  • [36] L.D. Hicks, A.J. Fry, V.C. Kurzweil, Electrochim. Acta. 50, 1039 (2004) http://dx.doi.org/10.1016/j.electacta.2004.08.003[Crossref]
  • [37] D. Kozlowski et al., J. Phys. Chem. A, 111, 1138 (2007) http://dx.doi.org/10.1021/jp066496+[Crossref]
  • [38] S.E. Blanco, F.H. Ferretti, Tetrahedron Lett. 48, 2577 (2007) http://dx.doi.org/10.1016/j.tetlet.2007.02.012[Crossref]
  • [39] M. J. Frisch et al. Gaussian 03, Revision B.03 (Gaussian, Inc., Pittsburgh PA, 2003)
  • [40] J.P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 78, 1396 (1997) http://dx.doi.org/10.1103/PhysRevLett.78.1396[Crossref]
  • [41] C. Amovilli et al., Adv. Quantum Chem. 32, 227 (1998) http://dx.doi.org/10.1016/S0065-3276(08)60416-5[Crossref]
  • [42] M. Cossi, V. Barone, J. Chem. Phys. 115, 4708 (2001) http://dx.doi.org/10.1063/1.1394921[Crossref]
  • [43] C. Adamo, V. Barone, Chem. Phys. Lett. 330, 152 (2000) http://dx.doi.org/10.1016/S0009-2614(00)01082-4[Crossref]
  • [44] H.H. Szmant, A.J. Basso, J. Am. Chem. Soc. 74, 4397 (1952) http://dx.doi.org/10.1021/ja01137a047[Crossref]
  • [45] E.R. Katzenellenbogen, G.E.K. Branch, J. Am. Chem. Soc. 69, 1615 (1947) http://dx.doi.org/10.1021/ja01199a013[Crossref]
  • [46] P.W. Shen, C. Zheng, D. Zhang, Y.X. Che, J. Synth. Cryst. 21, 280 (1992)
  • [47] I.F. Verpuson, R.P. Barnes, J. Am. Chem. Soc. 70, 3907 (1948) http://dx.doi.org/10.1021/ja01191a112[Crossref]
  • [48] A. Russel, J. Todd, C.L. Wilson, J. Chem. Soc. 1940 (1934) [Crossref]
  • [49] M.K. Seikel, T.A. Geissman J. Am. Chem. Soc. 72, 5720 (1950) http://dx.doi.org/10.1021/ja01168a094[Crossref]
  • [50] D. Jacquemin, J. Preat, V. Wathelet, E.A. Perpète, J.Chem.Phys. 124, 074104 (2006) http://dx.doi.org/10.1063/1.2166018[Crossref]
  • [51] D. Jacquemin, E.A. Perpète, Theor. Chem. Account 120, 405 (2008). http://dx.doi.org/10.1007/s00214-008-0424-9[Crossref]
  • [52] D.J. Tozer, R.D. Amos, N.C. Handy, B.O. Roos, L. Serrano-Andres, Mol. Phys. 97, 859 (1999) http://dx.doi.org/10.1080/00268979909482888[Crossref]
  • [53] A. Dreuw, M.H. Gordon, J. Am. Chem. Soc. 126, 4007 (2004) http://dx.doi.org/10.1021/ja039556n[Crossref]
  • [54] A. Dreuw, M.H. Gordon, Chem. Rev. 105, 4009 (2005) http://dx.doi.org/10.1021/cr0505627[Crossref]
  • [55] M.A. De Oliveira, H.A. Duarte, J.M. Pernaut, W.B. De Almeida, J. Phys. Chem. A104, 8256 (2000)
  • [56] C. Hansch, A. Leo, R.W. Taft, Chem. Rev. 91, 165 (1991) http://dx.doi.org/10.1021/cr00002a004[Crossref]
  • [57] D. Jacquemin, E.A. Perpète, G.E. Scuseria, I. Ciofini, C. Adamo, J. Chem. Theory Comput. 4, 123 (2008) http://dx.doi.org/10.1021/ct700187z[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-010-0058-3
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