DFT investigation on the tautomerization reaction and NBO analysis of the Acamprosate drug

Esmaeili, Bahareh; Beyramabadi, S. Ali; Khoshnood, Razieh Sanavi; Morsali, Ali

doi:10.13005/ojc/310434

Cited by 2 publications

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“…The average energy difference between the HOMO and LUMO of the title molecules are in the 3.87-4.49 eV range (Tables 4 and 5). This energy gap indicates that the title molecules are very stable [52][53][54][55]. Our results show that there are good linear correlations between σp and the energy difference between HOMO and LUMO in the studied molecules, see Table 8 and Figure 3.…”

Section: Correlation Between σP and The Energy Difference Between Thesupporting

confidence: 57%

Application of Hammett equation to intramolecular hydrogen bond strength in para-substituted phenyl ring of trifluorobenzoylacetone and 1-aryl-1,3-diketone malonates

et al. 2018

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The stability of two stable cis-enol forms in two categories of β-diketones, including para-substituted of trifluorobenzoylacetone (X-TFBA) and 1-aryl-1,3-diketone malonates (X-ADM, X: H, NO2, OCH3, CH3, OH, CF3, F, Cl, and NH2) has been obtained by different theoretical methods. According to our results, the energy difference between the mentioned stable chelated enol forms for the titled compounds is negligible. The theoretical equilibrium constants between the two stable cis-enol of the mentioned molecules are in excellent agreement with the reported experimental equilibrium constant. In addition, the effect of different substitutions on the intramolecular hydrogen bond strength has been evaluated. The correlation between Hammett para-substituent constants, σp. with the theoretical and experimental parameters related to the strength of hydrogen bond in p-X-TFBA and p-X-ADM molecules also investigated by means of density functional theory calculations. The electronic effects of para-substitutions on the intramolecular hydrogen bond strength were determined by NMR and IR data related to intramolecular hydrogen bond strength, geometry, natural bond orbital results, and topological parameters. These parameters were correlated with the Hammett para-substituent constants, σp. Good linear correlations between σp and the several parameters related to the hydrogen bond strength, in this study were obtained.

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Section: Correlation Between σP and The Energy Difference Between Thesupporting

confidence: 57%