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

• Autorzy: Yunsheng Xue , Jie Mou , Yi Liu , Xuedong Gong , Yihua Yang , Lin An
• 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

EN

Chalcones; TD-DFT; PCM; Absorption spectrum; Substituent effect

• Czasopismo: Open Chemistry
• Rocznik: 2010
• Tom: 8
• Numer: 4
• Strony: 928-936

Daty

wydano

2010-08-01

online

2010-06-17

Twórcy

autor

Yunsheng Xue

• Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China,

autor

Jie Mou

• Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China

autor

Yi Liu

• Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China

autor

Xuedong Gong

• Department of Chemistry, Nanjing University of Science and Technology, Nanjing, 210094, China

autor

Yihua Yang

• Chemical and Biological Pharmaceutical Engineering Research Center, School of Pharmacy, Xuzhou Medical College, Xuzhou, Jiangsu, 221004, China

autor

Lin An

• 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]

Identyfikatory

DOI

10.2478/s11532-010-0058-3