Research Article
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Theoretical study of the effect of heteroatom on the electronic and molecular properties of isoindoline monomers

Year 2018, Volume: 2 Issue: 1, 31 - 38, 15.06.2018

Abdelkader Ladjarafı , Hacène Meghezzı

Abstract

Theoretical calculations
were carried out in the gas phase and in solution in order to study the
influence of the heteroatom on the electronic and structural properties of some
isoindoline derivatives and likewise to demonstrate the effect of the
solvent on the tautomeric process encountered in this type of equilibrium. The
most stable structures are analyzed and the possible equilibrium displacements
are studied. Results of the total energies obtained with the HF, MP2 and DFT
methods show firstly, that the isoindoline forms are the most stable,
and secondly, that the replacement of the NH heteroatom by an oxygen heteroatom
increases the stability of the compound. Calculations in solution indicate that
the electronic properties of the heterocycle are influenced by the nature of
the solvent which is used. However, all tautomeric forms are more stable in
DMSO than in THF. The predominance of the isoindoline form in gas phase
and in solution is confirmed as experimentally observed.

Keywords

isoindoline isoindole heterocycle heteroatom solvent effect MP2 DFT

References

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Year 2018, Volume: 2 Issue: 1, 31 - 38, 15.06.2018

Abdelkader Ladjarafı , Hacène Meghezzı

Abstract

References

  • (a) M. Iman, A. Saadabadi, A. Davood, H. Shafaroodi, A. Nikbakht, A. Ansari and M. Abedini, Iran. J. Pharm. Res., 16 (2017) 586-595 (b) A. Abastiyan and M. Yosuva Suvaikin, Adv. Appl. Sci. Res., 3 (2012) 45-50 (c) H. Mujagia, A.C. Bruce, Z. Mujagiæ, Croatian Med., 43 (2002) 274-285 (d) D. Berger, R. Citarella, M. Dutia, L. Grenberger, W. Hallet, D. Poweel, J. Med. Chem., 42 (1999) 2145-2161 (e) P. Sanna, G. Cignarella, V. Ananiaa, R.M.S. Siri, M.S. Desole, Farmaco. Ed. Sci., 40 (1985) 777-785 (f) G. Cignarella, P. Sanna, J. Med. Chem. 24 (1981) 1003-1006.
  • M. Lı´dia, L.P. Castro, A.L. Machado, A.M. Carlos, F.C. Lugnier, V.L.C. Gonc, A.D. Moraesc, J. Eliezer, Bioorg. Med. Chem., 10 (2002) 3067-3073.
  • (a) A. Davood, M. Amini, L. Azimidoost, S. Rahmatpour, A. Nikbakht, M. Iman, H. Shafaroodi and A. Ansari, Med. Chem. Res., 22 (2013) 3177-3184 (b) A. AbdeI-Monem, A. Hafez, Arch. Pharm. Res., 27 (2004) 495-501.
  • S. Kumar, N. Kumar, P. Roy, S.M. Sondhi, Mol. Divers., 17 (2013) 753-766.
  • L.M. Ching, W.L. Browne, R. Tchernegovski, T. Gregory, B.C. Baguley & B.D. Palmer, Brtish. J. Cancer, 78 (1998) 336-343.
  • H. Stanton, L.K. Roberto, G. Chui, C.H. Marcus, C.W. Yuen, L. Cheung, E.F. Tanga, S.C. Chana, Bioorg. Med. Chem., 16 (2008) 3626-3631.
  • L. Min, S. Wan, Y. Yang, Y. Wen-yuan, L. Zhong-jun & C. Jing-rong, Acta. Pharmacol. Sin., 30 (2009) 134-140.
  • R.K. Bhatia, Curr. Top. Med. Chem., 17 (2017) 189-207.
  • (a) S. Desai, V. Girija Sastry, World J. Pharm. Pharm. Sci., 5 (2016) 1543-1549 (b) P.M. Shivakumar, S.M. Geetha Babu, D. Mukesh, Chem. Pharm. Bull., 55 (2007) 44-49.
  • M. Durand, V. Molinier, W. Kunz et J.M. Aubry, Chem. Eur. J., 17 (2011) 5155-5164.
  • F.P. Miller, A.F. Vandome, J. McBrewster, Méthode Ab Initio de Chimie Quantique, Alpha script Publishing, UK, 2010.
  • (a) D.R. Hartree, Proc. Cambridge Phil. Soc., 24 (1928) 89-110 (b) V. Fock, Z. Physik., 61 (1930) 126-148.
  • (a) P. Hohenberg, W. Kohn, Phys. Rev. B, 136 (1964) 864-871 (b) W. Kohn, L.J. Sham, Phys. Rev. A, 140 (1965) 1133-1138.
  • W. Koch, M.C. Holthausen, A Chemist’s Guide to Density Functional Theory. Wiley-VCH, Weinheim, 2000, 33-89.
  • A.D. Becke, J. Chem. Phys., 98 (1993) 1372-1377.
  • C. Lee, W. Yang, R.G. Parr, Phys. Rev. B, 37 (1988) 785-789.
  • J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev., 105 (2005) 2999-3094.
  • M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant and al., Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004. http://www.gaussian.com
  • ChemOffice 8.0, CambridgeSoft.Com, Cambridge, M.A., USA, 2008.
  • R.S. Mulliken, J. Chem. Phys., 23 (1955) 1833-1840.
  • B. Kripli, G. Baráth, É. Balogh-Hergovich, M. Giorgi, A.J. Simaan, L. Párkányi, J.S. Pap, J. Kaizer, G. Speier, Inorg. Chem. Commun., 14 (2011) 205-209.
  • R. Baharfar and S. Mohajer, Helvetica. Chimica. Acta., 95 (2012) 185-190.
  • J. Singh, T. Singha, A. Naskar, M. Kundu, R.K. Harwansh, A. Mondal, T. Ghosh and T.K. Maity, Pharmacologyonline, 2 (2011) 976-987.
There are 23 citations in total.

Details

Journal Section Research Article
Authors

Abdelkader Ladjarafı

Hacène Meghezzı This is me

Publication Date June 15, 2018
Submission Date November 28, 2017
Published in Issue Year 2018 Volume: 2 Issue: 1

Cite

APA Ladjarafı, A., & Meghezzı, H. (2018). Theoretical study of the effect of heteroatom on the electronic and molecular properties of isoindoline monomers. Turkish Computational and Theoretical Chemistry, 2(1), 31-38.
AMA Ladjarafı A, Meghezzı H. Theoretical study of the effect of heteroatom on the electronic and molecular properties of isoindoline monomers. Turkish Comp Theo Chem (TC&TC). June 2018;2(1):31-38.
Chicago Ladjarafı, Abdelkader, and Hacène Meghezzı. “Theoretical Study of the Effect of Heteroatom on the Electronic and Molecular Properties of Isoindoline Monomers”. Turkish Computational and Theoretical Chemistry 2, no. 1 (June 2018): 31-38.
EndNote Ladjarafı A, Meghezzı H (June 1, 2018) Theoretical study of the effect of heteroatom on the electronic and molecular properties of isoindoline monomers. Turkish Computational and Theoretical Chemistry 2 1 31–38.
IEEE A. Ladjarafı and H. Meghezzı, “Theoretical study of the effect of heteroatom on the electronic and molecular properties of isoindoline monomers”, Turkish Comp Theo Chem (TC&TC), vol. 2, no. 1, pp. 31–38, 2018.
ISNAD Ladjarafı, Abdelkader - Meghezzı, Hacène. “Theoretical Study of the Effect of Heteroatom on the Electronic and Molecular Properties of Isoindoline Monomers”. Turkish Computational and Theoretical Chemistry 2/1 (June 2018), 31-38.
JAMA Ladjarafı A, Meghezzı H. Theoretical study of the effect of heteroatom on the electronic and molecular properties of isoindoline monomers. Turkish Comp Theo Chem (TC&TC). 2018;2:31–38.
MLA Ladjarafı, Abdelkader and Hacène Meghezzı. “Theoretical Study of the Effect of Heteroatom on the Electronic and Molecular Properties of Isoindoline Monomers”. Turkish Computational and Theoretical Chemistry, vol. 2, no. 1, 2018, pp. 31-38.
Vancouver Ladjarafı A, Meghezzı H. Theoretical study of the effect of heteroatom on the electronic and molecular properties of isoindoline monomers. Turkish Comp Theo Chem (TC&TC). 2018;2(1):31-8.
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Journal Full Title: Turkish Computational and Theoretical Chemistry


Journal Abbreviated Title: Turkish Comp Theo Chem (TC&TC)