Experimental and theoretical study on solvent and substituent effect in 3-(4-substituted)phenylamino)isobenzofuran-1(3H)-ones

Nevena Prlainović, Milica Rančić, Ivana Stoiljković, Jasmina Nikolic, Saša Drmanić, Ismail Ajaj, Aleksandar Marinković

Abstract


The substituent and solvent effect on solvatochromism in3-((4-substituted)phenylamino)isobenzofuran-1(3H)-ones were studied using experimental and theoretical methodology. The effect of specific and non-specific solvent–solute interactions on the UV-Vis absorption maxima shifts were evaluated by using the Kamlet-Taft and Catalán solvent parameter sets. The experimental results were studied by DFT and TD-DFT methods. The HOMO/LUMO energies (EHOMO/ELUMO) and energy gap (Egap) values, as well as the mechanism of electronic excitations and the changes in the electron density distribution in both ground and excited states of the investigated molecules were studied by the calculation in the gas phase. The electronic excitations were calculated by TD-DFT method in solvent methanol. It was found that both substituents and solvents influence the degree of π-electron conjugation of the synthesized molecules and affect the intramolecular charge transfer character. 


Keywords


phthalides; solvatochromism; substituent effect; LSER; quantum chemical calculation.

Full Text:

PDF (2,260 kB)

References


G. Lin, S. S.-K. Chan, H.-S. Chung, S.-L. Li, Stud. Nat. Prod. Chem.32 (2005) 611

R. Karmakar, P. Pahari, D. Mal, Chem. Rev. 114 (2014) 6213

Y.-Q.Zhu, J.-X. Li, T.-F.Han, J.-L. He,K. Zhu, Eur. J. Org. Chem. 2017 (2017) 806

T. Saito, T. Itabashi, D. Wakana, H, Takeda, T. Yaguchi, K. Kawai, T. Hosoe, J. Antibiot. 69 (2016) 89

R. A. Limaye, V. B. Kumbhar, A. D. Natu, M. V. Paradkar, V. S. Honmore, R. R. Chauhan, S. P. Gample, D. Sarkar, Bioorg. Med. Chem. Lett .23 (2013) 711

G. Strobel, E. Ford, J. Worapong, J. K. Harper, A. M. Arif, D. M. Grant, P. C. W. Fung, R. M. W. Chau, Phytochemistry 60 (2002) 179

S.F. Brady, M.M. Wagenaar, M.P. Sing, J.E. Janso, Org. Lett. 2 (2000) 4043

T. H. Chou, I. S. Chen, T. L. Hwang, T. C. Wang, T. H. Lee, L. Y. Cheng, Y. C. Chang, J. Y. J. Y. Cho, J. J. Chen, J. Nat. Prod., 71 (2008) 1692

L. P. L. Logrado, C. O. Santos, L. A. S. Romeiro, A. M. Costa, J. R. O. Ferreira, B. C. Cavalcanti, O. M. de Moraes, L. V. Costa-Lotufo, C. Pessoa, M. L. dos Santos, Eur. J. Med. Chem. 45 (2010) 3480

M.Rančić,N. Trišović, M. Milčić, G. Ušćumlić, A. Marinković,Spectrochim. Acta A 86 (2012)500

A. Sarkar, P. Banerjee, S. U. Hossain, S. Bhattacharya, S. C. Bhattacharya, Spectrochim. Acta A 72 (2009) 1097

C.Reichardt, Solvents and Solvent Effects in Organic Chemistry,3rd, Updated and Enlarged Edition, Wiley-VCH, Weinheim, Germany, 2003, p. 432

M. J. Kamlet, J. L. M. Abbound, R. W. Taft, An examination of linear solvation energy relationships,inProgress in Physical Organic Chemistry,vol. 13, R.W. Taft, Ed(s).,Wiley, New York, USA, 1981, p. 485

J. Catalán, J. Phys. Chem. B 113 (2009) 5951

T. Yanai, D. Tew, N. Handy,Chem. Phys. Lett. 393 (2004) 51

Gaussian 09, Revision C.01, Gaussian Inc., 2009, Wallingford, CT

M. S. Masoud, R. M. I. Elsamra, S. S. Hemdan, J. Serb. Chem. Soc. 82 (2017), doi: 10.2298/JSC170204032M

M. Faraji, A. Farajtabar, J. Serb. Chem. Soc. 81 (2016) 1161

D. R. Brkić, J. B. Nikolić, A. R. Božić, V. D. Nikolić, A. D. Marinković, H. Elshaflu, S. Ž. Drmanić, J. Serb. Chem. Soc. 81 (2016) 979

A. Amer, H. Zimmer, J. Heterocyclic Chem. 18 (1981) 1625

S. N. Khattab, S. Y. Hassan, A. El-Faham, A. M. M. El Massry, A. Amer, J. Heterocyclic Chem. 44 (2007) 617

D. Jacquemin, A. Planchat, C. Adamo, B. Mennucci, J. Chem. Theory Comput., 8 (2012) 2359.




DOI: http://dx.doi.org/10.2298/JSC170408003P

Refbacks

  • There are currently no refbacks.


Copyright (c) 2018 J. Serb. Chem. Soc.

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

IMPACT FACTOR 0.822 (131 of 166 journals)
5 Year Impact Factor 1.015 (118 of 166 journals)