Use of Local Softness for the Interpretation of Reaction Mechanisms

Nguyen, Minh Tho; Chandra, Asit K.

doi:10.3390/i3040310

Cited by 88 publications

(30 citation statements)

References 44 publications

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“…The Fukui function f ðrÞ [9][10][11] is defined as a derivative of electronic density qðrÞ versus number of electrons N at a constant external potential mðrÞ (fixed nuclei):…”

Section: Fukui Functionmentioning

confidence: 99%

“…Our former calculations on models systems [7,8] have shown that the condensed Fukui function [9][10][11] can be useful in the prediction of the reactivity in silico of highly symmetrical and highly delocalized molecules like nanotubes and fullerenes. A novelty of the present study is the development of a simple model to predict the reactivity of conjugated polycyclic aromatic hydrocarbons of the general formula C 6n 2 H 6n with hydroxyl radicals.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical and computational modelling of functionalization energy for the $$ {\rm{C}}_{{6{n}}^{2}} {\rm{H}}_{6{n}} $$ polycyclic aromatic hydrocarbons (PAHs) homologue series

Fusaro

2011

Struct Chem

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Based on the free electron metallic disc model, the derivation of a simple expression for evaluation of the Fukui function for the molecular models of polycyclic aromatic hydrocarbons (PAHs) of the general formula C 6n 2 H 6n was described. We also investigated the functionalization energy with OH radicals for the molecular models of PAHs (n = 1-6). Our metallic disc model-based functionalization reaction energy was in agreement with the DFT:B3LYP/6-31G(d) calculated values. Asymptotic values of the functionalization energies (n ! 1) were predicted to be -30.1 ± 0.1 and -8.7 ± 0.1 kcal/mol for the external and internal border carbon atoms, respectively.

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“…The Fukui function f ðrÞ [9][10][11] is defined as a derivative of electronic density qðrÞ versus number of electrons N at a constant external potential mðrÞ (fixed nuclei):…”

Section: Fukui Functionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Theoretical and computational modelling of functionalization energy for the $$ {\rm{C}}_{{6{n}}^{2}} {\rm{H}}_{6{n}} $$ polycyclic aromatic hydrocarbons (PAHs) homologue series

Fusaro

2011

Struct Chem

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“…21,22 The final global reactivity descriptor, molecular softness, is inversely related to the molecular hardness. 19,20,22 Local QC indices describe properties of atoms in a molecule. The atomic charge provides a local reactivity index that is defined as the difference between the nuclear charge and the total (inner and valence) electron density attributed to the atom.…”

Section: Introductionmentioning

confidence: 99%

“…15,21,22 Softness is the Fukui function scaled by the molecular hardness. 19 Consequently reactivity values may be compared between atoms in different molecules using the atomcondensed softness.…”

Section: Introductionmentioning

confidence: 99%

Rapid Prediction of Chemical Metabolism by Human UDP-glucuronosyltransferase Isoforms Using Quantum Chemical Descriptors Derived with the Electronegativity Equalization Method

et al. 2004

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This study aimed to evaluate in silico models based on quantum chemical (QC) descriptors derived using the electronegativity equalization method (EEM) and to assess the use of QC properties to predict chemical metabolism by human UDP-glucuronosyltransferase (UGT) isoforms. Various EEM-derived QC molecular descriptors were calculated for known UGT substrates and nonsubstrates. Classification models were developed using support vector machine and partial least squares discriminant analysis. In general, the most predictive models were generated with the support vector machine. Combining QC and 2D descriptors (from previous work) using a consensus approach resulted in a statistically significant improvement in predictivity (to 84%) over both the QC and 2D models and the other methods of combining the descriptors. EEM-derived QC descriptors were shown to be both highly predictive and computationally efficient. It is likely that EEM-derived QC properties will be generally useful for predicting ADMET and physicochemical properties during drug discovery.

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“…Fukui function f r ð Þ [19][20][21] is defined as a derivative of electronic density q r ð Þ versus the total number of electrons N at constant external potential v generated by the nuclei. Thus,…”

Section: Theoretical Backgroundmentioning

confidence: 99%

Derivation of the linear relationship between SWCNTs functionalization energies and sidewall curvature

Fusaro

2012

Struct Chem

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A simple linear relationship between the functionalization reaction energies for the exohedral monovalent addition on the surface of an ideal, infinitely long, single-walled carbon nanotube (SWCNT) and the reciprocal SWCNT radius has been derived employing the hardsoft acid basis principle and the tight binding model. The slope of the derived linear relationship is a function of the effective number of valence electrons involved in the functionalization reaction. The intercept of the derived linear relationship, equal to the reaction energies on a planar graphite surface, is a function of the electrophilicity of the monovalent addend and of the condensed Fukui function of its reacting atom. The theoretical predictions of this simple formula are coherent with the computational density functional theory data reported in the literature.

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Use of Local Softness for the Interpretation of Reaction Mechanisms

Cited by 88 publications

References 44 publications

Theoretical and computational modelling of functionalization energy for the $$ {\rm{C}}_{{6{n}}^{2}} {\rm{H}}_{6{n}} $$ polycyclic aromatic hydrocarbons (PAHs) homologue series

Theoretical and computational modelling of functionalization energy for the $$ {\rm{C}}_{{6{n}}^{2}} {\rm{H}}_{6{n}} $$ polycyclic aromatic hydrocarbons (PAHs) homologue series

Rapid Prediction of Chemical Metabolism by Human UDP-glucuronosyltransferase Isoforms Using Quantum Chemical Descriptors Derived with the Electronegativity Equalization Method

Derivation of the linear relationship between SWCNTs functionalization energies and sidewall curvature

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