A quantum chemical study on a set of non-imidazole H3 antihistamine molecules

Costa, Edson B.; Trsic, Milan

doi:10.1016/j.jmgm.2010.01.003

Cited by 8 publications

(7 citation statements)

References 36 publications

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“…The concept of the frontier orbital, introduced by Fukui around 1952, relates reactivity with the properties of two molecular orbitals: HOMO and LUMO. In fact, one application of the HOMO−LUMO argument is the description of the cycloaddition reactions. − It should be kept in mind, however, that the HOMO−LUMO argument has certain limitations and new efforts are necessary to understand when the HOMO energy works and when it does not; currently, that important topic in chemistry has been the target of several research groups. − More recently, the frontier effective-for-reaction molecular orbital (FERMO) concept has emerged as a powerful approach for studying this situation. − The localization and the composition of the orbitals can reveal a frontier molecular orbital close to the HOMO with large contribution in atoms present at the active site (APAS). Actually, a large MO contribution in APAS can fit our orbital choice criterion, because they are common to all of the studied compounds and are mainly located where the reaction takes place.…”

Section: Introductionmentioning

confidence: 99%

Orbital Signatures as a Descriptor of Regioselectivity and Chemical Reactivity: The Role of the Frontier Orbitals on 1,3-Dipolar Cycloadditions

et al. 2011

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The FERMO concept emerges as a powerful and innovative implement to investigate the role of molecular orbitals applied to the description of breakage and formation of chemical bonds. In this work, Hartree-Fock (HF) theory and density functional (DFT) calculations were performed for a series of four reactions of 1,3-dipolar cycloadditions and were analyzed by molecular orbital (MO) energies, charge transfer, and molecular dynamics (ADMP) techniques for direct dynamics using the DFT method. The regioselectivity for a series of four 1,3-dipolar cycloaddition reactions was studied here using global and local reactivity indexes. We observed that the HOMO energies are insufficient to describe the behavior of these reactions when there is the presence of heteroatoms. By using the frontier effective-for-reaction molecular orbital (FERMO) concept, the reactions that are driven by HOMO, and those that are not, can be better explained, independent of the calculation method used, because both HF and Kohn-Sham methodologies lead to the same FERMO.

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Section: Introductionmentioning

confidence: 99%

Orbital Signatures as a Descriptor of Regioselectivity and Chemical Reactivity: The Role of the Frontier Orbitals on 1,3-Dipolar Cycloadditions

et al. 2011

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“…Da Costa and Trsic [14] reported QSAR models to a set of 28 4-phenoxypiperidine derivatives (p K i 5.27-9.20) previously published by Dvorak et al (Fig. 6 ) [42].…”

Section: Qsar Studies On H3r Antagonistsmentioning

confidence: 99%

“…Low (left) and high (right) affinity molecules present in the set studied by da Costa and Trsic [14]. …”

Section: Fig (1)mentioning

confidence: 99%

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QSAR Modeling of Histamine H3R Antagonists/inverse Agonists as Future Drugs for Neurodegenerative Diseases

Corrêa

Fernandes

2018

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“…In Equation (7), the FERMO corresponds to a HOMO- X , a given occupied molecular orbital showing the greatest contribution to compose the reactive center [36]. All these cited reactivity indexes can bring thermodynamic as much as kinetics considerations [37].…”

Section: Introductionmentioning

confidence: 99%

Quantitative Structure–Property Relationship (QSPR) Models for a Local Quantum Descriptor: Investigation of the 4- and 3-Substituted-Cinnamic Acid Esterification

et al. 2015

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Abstract:In this work, the theoretical description of the 4-and 3-substituted-cinnamic acid esterification with different electron donating and electron withdrawing groups was performed at the B3LYP and M06-2X levels, as a two-step process: the O-protonation and the nucleophile attack by ethanol. In parallel, an experimental work devoted to the synthesis and characterization of the substituted-cinnamate esters has also been performed. In order to quantify the substituents effects, quantitative structure-property relationship (QSPR) models based on the atomic charges, Fukui functions and the Frontier Effective-for-Reaction Molecular Orbitals (FERMO) energies were investigated. In fact, the Fukui functions, ƒ + C and ƒ − O, indicated poor correlations for each individual step, and in contrast with the general literature, the O-protonation step is affected both by the FERMO energies and the O-charges of the carbonyl group. Since the process was shown to not be totally described by either charge-or frontier-orbitals, it is proposed to be frontier-charge-miscere controlled. Moreover, the observed OPEN ACCESSMolecules 2015, 20 17494 trend for the experimental reaction yields suggests that the electron withdrawing groups favor the reaction and the same was observed for Step 2, which can thus be pointed out as the determining step.

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A quantum chemical study on a set of non-imidazole H3 antihistamine molecules

Cited by 8 publications

References 36 publications

Orbital Signatures as a Descriptor of Regioselectivity and Chemical Reactivity: The Role of the Frontier Orbitals on 1,3-Dipolar Cycloadditions

Orbital Signatures as a Descriptor of Regioselectivity and Chemical Reactivity: The Role of the Frontier Orbitals on 1,3-Dipolar Cycloadditions

QSAR Modeling of Histamine H3R Antagonists/inverse Agonists as Future Drugs for Neurodegenerative Diseases

Quantitative Structure–Property Relationship (QSPR) Models for a Local Quantum Descriptor: Investigation of the 4- and 3-Substituted-Cinnamic Acid Esterification

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