Electronic absorption spectroscopy of the benzimidazolic analogs of chalcone
Abstract
The electronic absorption spectra of the benzimidazolic analogs of chalcone were analyzed theoretically in the framework of ESSA approach. The benzimidazole moiety was shown to influence the spectral characteristics of the investigated compounds via the intensification of intramolecular donor-acceptor interactions at their electronic excitation.
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S.V. Kostanecki, G. Rossbach. Uever die sechs isomeren Monooxybenzalacetophenone (Monooxychalkone). Berichte der deutschen chemischen Gesellschaft 29 (1896) 1488-1494.
S.V. Kostanecki, J. Tambor. Uever die Einwirkung von Benzaldehyd auf Acetophenon. Berichte der deutschen chemischen Gesellschaft 32 (1899) 1921-1926.
N.D. Dhar. The chemistry of chalcones and related compounds. N-Y: A Wiley-Interscience publication, 1981. 285 p.
S.M. Desenko, V.D. Orlov. Azageterocikly' na osnove aromaticheskih nepredel'ny'h ketonov. Har'kov: Folio, 1998. 148 s.
V.A. Сhebanov, S.M. Desenko, T.W.Gurley. Azaheterocycles based on α,β-unsaturated car-bonyls. Berlin: Springer, 2008. 210 p.
J-C. Le Bail, C. Pouget, C. Fagnere, J-P. Basly, A-J. Chulia, G. Habrioux. Chalcones are po-tent inhibitors of aromatase and 17β-hydroxysteroid dehydrogenase activities. Life Sciences 68 (2001) 751-761.
D.K. Mahapatra, S.K. Bharti. Anti-cancer chalcones: Structural and molecular target perspec-tives. European Journal of Medicinal Chemistry 98 (2015) 69-114.
D.K. Mahapatra, V. Asati, S.K. Bharti. Chalcones and their therapeutic targets for the man-agement of diabetes: Structural and pharmacological perspectives. European Journal of Me-dicinal Chemistry 98 (2015) 839-865.
D.K. Mahapatra, S.K. Bharti. Therapeutic potential of chalcones as cardiovascular agents. Life Sciences. 148 (2016) 154-172.
A. Roque, J.C. Lima, A.J. Parola, F. Pina. Substitution and solvent effects in the chalcones isomerization barrier of flavylium photochromic systems. Photochem. Photobiol. Sci. 6 (2007) 381-385.
J.H. Kim, S.Y. Ban, Q. Zhang, G.W. Kim, M.J. Cho, D.H. Choi. Effect of Photocrosslinking on Photochromism of Chalcone-based Polymeric Materials bearing Spiropyran Dye. Molecu-lar Crystals and Liquid Crystals. 445 (2006) 307-314.
L. Ming, Z.K. Si, Q. Zhang, Q.R. Sheng, M.Z. Xue,Y.G. Liu. Photochemical characterization of bi-functional compounds containing indolinospiropyran and chalcone groups. Research on Chemical Intermediates. 41 (2015) 3017-3029.
V.G. Mitina, L.A. Kutulya, A.A. Suhorukov. Problemy' fizicheskoy organicheskoy himii. Har'kov: Visch'a shkola, 1989. 152 s.
A.V. Luzanov. Struktura e`lektronnogo voz-bujdeniya molekul v kvantovo-himicheskih modelyah. Uspehi himii 64 (1980) 2086-2095.
A.D. Becke. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98 (1993) 5648-5652.
D.E. Woon, T.H. Dunning. Gaussian basis sets for use in correlated molecular calculations. III. The atoms aluminum through argon, J. Chem. Phys. 98 (1993) 1358-1371.
M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox. Gaussian, Inc., Wallingford CT, 2010. Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford CT, 2010.
T. Steiner. The Hydrogen Bond in the Solid State. Angew. Chem. Int. Ed. 41 (2002) 48-76.
R.F.W. Bader, Atoms in molecules, Acc. Chem. Res. 18 (1985) 9-15.
R.F.W. Bader, A quantum theory of molecular structure and its applications, Chem. Rev. 91 (1991) 893-928.
R.F.W. Bader, A bond path: a universal indicator of bonded interactions, J. Phys. Chem. A 102 (1998) 7314-7323.
R.F.W. Bader, Bond paths are not chemical bonds, J. Phys. Chem. A 113 (2009) 10391-10396.
A. Gordon, R. Ford. Sputnik himika. M.:Mir, 1976. 541 s.
A.V. Luzanov, O.A. Zhikol, Electron invariants and excited state structural analysis for elec-tronic transitions within CIS, RPA, and TDDFT models, Int. J. Quant. Chem. 110 (2010) 902-924.
E.J. Bylaska, W.A. de Jong, N. Govind, K. Kowalski, T.P. Straatsma, M. Valiev, D. Wang, E. Apra, T.L. Windus, J. Hammond, P. Nichols, S. Hirata, M.T. Hackler, Y. Zhao, P.-D. Fan, R.J. Harrison, M. Dupuis, D.M.A. Smith, J. Nieplocha, V. Tipparaju, M. Krishnan, Q. Wu, T. Van Voorhis, A.A. Auer, M. Nooijen, E. Brown, G. Cisneros, G.I. Fann, H. Fruchtl, J. Garza, K. Hirao, R. Kendall, J.A. Nichols, K. Tsemekhman, K. Wolinski, J. Anchell, D. Bernholdt, P. Borowski, T. Clark, D. Clerc, H. Dachsel, M. Deegan, K. Dyall, D. Elwood, E. Glendening, M. Gutowski, A. Hess, J. Jaffe, B. Johnson, J. Ju, R. Kobayashi, R. Kutteh, Z. Lin, R. Littlefield, X. Long, B. Meng, T. Nakajima, S. Niu, L. Pollack, M. Rosing, G. San-drone, M. Stave, H. Taylor, G. Thomas, J. van Lenthe, A. Wong, Z. Zhang. "NWChem, A Computational Chemistry Package for Parallel Computers, Version 5.1" (2007), Pacific Northwest National Laboratory, Richland, Washington 99352-0999, USA.
B.I. Stepanov. Vvedenie v himiyu i tehnologiyu organicheskih krasiteley. M: Himiya, 1984. 592 s.
