Journal ArticleDOI
Nucleophilicity and site selectivity of commonly used arenes and heteroarenes.
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TLDR
Four different arene and heteroarene series have been subjected to local nucleophilicity analysis in order to predict the site selectivity in electrophilic aromatic substitution reactions (EAS) with excellent correlation with the experimental result.Abstract:
By using the inverse concept of electrophilicity and nucleophilicity and with four different available equations from literature for electrophilicity and electrodonating power, the nucleophilicity values of 69 commonly used arenes and heteroarenes have been calculated at the B3LYP/6-311+G(d,p) level of theory. The linearity between the nucleophilicity and Hammett sigma and sigma(p) values has been chosen as a test to judge the goodness of the methods used. Finally four different arene and heteroarene series (substituted indoles, phenols, pyrroles, and anisoles) have been subjected to local nucleophilicity analysis in order to predict the site selectivity in electrophilic aromatic substitution reactions (EAS). In each case we have obtained excellent correlation with the experimental result.read more
Citations
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Applications of the Conceptual Density Functional Theory Indices to Organic Chemistry Reactivity.
TL;DR: Global quantities like the electronic chemical potential μ, the electrophilicity ω and the nucleophilicity N indices, and local condensed indices, as the most relevant indices for the study of organic reactivity are discussed.
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The nucleophilicity N index in organic chemistry
Luis R. Domingo,Patricia Pérez +1 more
TL;DR: This comparative study allows to assert that the nucleophilicity N index is a measure of the nuclephilicity of complex organic molecules displaying concurrently electrophilic and nucleophilic behaviors.
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Update 2 of: Electrophilicity Index
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Pinacol Boronates by Direct Arene Borylation with Borenium Cations
TL;DR: In this article, it was demonstrated that catecholato ligated borenium cations, generated in solution from CCB, react as electrophiles with activated arenes and hetarenes to give a variety of pinacol boronates after quenching with pinacolic acid.
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Enantioselective synthesis of triarylmethanes by chiral imidodiphosphoric acids catalyzed Friedel-Crafts reactions.
TL;DR: These two efficient Friedel-Crafts alkylation processes feature low catalyst loading, broad functional group compatibilities, and the potential to provide practical pathways for the synthesis of enantioenriched bioactive triarylmethanes.
References
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Self-Consistent Equations Including Exchange and Correlation Effects
Walter Kohn,L. J. Sham +1 more
TL;DR: In this paper, the Hartree and Hartree-Fock equations are applied to a uniform electron gas, where the exchange and correlation portions of the chemical potential of the gas are used as additional effective potentials.
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Absolute hardness: companion parameter to absolute electronegativity
Robert G. Parr,Ralph G. Pearson +1 more
TL;DR: In this paper, a property called absolute hardness eta is defined for neutral and charged species, atomic and molecular, for both hard and soft acids and bases, by making use of the hypothesis that extra stability attends bonding of A to B when the ionization potentials of A and B in the molecule are the same.
Journal ArticleDOI
Conceptual density functional theory.
TL;DR: This chapter discusses the development of DFT as a tool for Calculating Atomic andMolecular Properties and its applications, as well as some of the fundamental and Computational aspects.