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

Yıl 2018, Cilt: 2 Sayı: 1, 31 - 38, 15.06.2018

Abdelkader Ladjarafı Hacène Meghezzı

Öz

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.

Anahtar Kelimeler

isoindoline isoindole heterocycle heteroatom solvent effect MP2 DFT

Kaynakça

  • (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.

Yıl 2018, Cilt: 2 Sayı: 1, 31 - 38, 15.06.2018

Abdelkader Ladjarafı Hacène Meghezzı

Öz

Kaynakça

  • (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.
Toplam 23 adet kaynakça vardır.

Ayrıntılar

Bölüm Research Article
Yazarlar

Abdelkader Ladjarafı

Hacène Meghezzı Bu kişi benim

Yayımlanma Tarihi 15 Haziran 2018
Gönderilme Tarihi 28 Kasım 2017
Yayımlandığı Sayı Yıl 2018 Cilt: 2 Sayı: 1

Kaynak Göster

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). Haziran 2018;2(1):31-38.
Chicago Ladjarafı, Abdelkader, ve Hacène Meghezzı. “Theoretical Study of the Effect of Heteroatom on the Electronic and Molecular Properties of Isoindoline Monomers”. Turkish Computational and Theoretical Chemistry 2, sy. 1 (Haziran 2018): 31-38.
EndNote Ladjarafı A, Meghezzı H (01 Haziran 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 ve H. Meghezzı, “Theoretical study of the effect of heteroatom on the electronic and molecular properties of isoindoline monomers”, Turkish Comp Theo Chem (TC&TC), c. 2, sy. 1, ss. 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 (Haziran 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 ve Hacène Meghezzı. “Theoretical Study of the Effect of Heteroatom on the Electronic and Molecular Properties of Isoindoline Monomers”. Turkish Computational and Theoretical Chemistry, c. 2, sy. 1, 2018, ss. 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.
 Kapak Resmi İndir

Journal Full Title: Turkish Computational and Theoretical Chemistry


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