PL EN


Preferences help
enabled [disable] Abstract
Number of results
Journal
2010 | 8 | 4 | 928-936
Article title

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

Content
Title variants
Languages of publication
EN
Abstracts
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. [...]
Publisher
Journal
Year
Volume
8
Issue
4
Pages
928-936
Physical description
Dates
published
1 - 8 - 2010
online
17 - 6 - 2010
References
  • [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]
Document Type
Publication order reference
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-010-0058-3
Identifiers
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.