Publicaciones 2011-2020

@article{RN329,
title = {Origins of the Anrorc Reactivity in Nitroimidazole Derivatives},
author = { S. Gallardo-Fuentes and R. Contreras and R. Ormazabal-Toledo},
url = {/brokenurl#<Go to ISI>://WOS:000372252700049},
doi = {10.1039/c6ra00199h},
issn = {2046-2069},
year = {2016},
date = {2016-01-01},
journal = {Rsc Advances},
volume = {6},
number = {30},
pages = {25215-25221},
abstract = {The mechanism of the ANRORC-like ring transformation of nitroimidazole derivatives towards aniline has been studied by fully exploring the potential energy surface (PES). For this purpose the reaction of some aniline derivatives towards 1,4-dinitro-1H-imidazole, 2-methyl-1,4-dinitro-1H-imidazole and 5-methyl1,4-dinitro-1H-imidazole and have been employed as model reactions. The study reveals that the most favorable path involves an initial amine attack at the C(5)-C(4) bond of the imidazole moiety, where the imidazole distortion appears to be the main factor for the favored nucleophilic attack on the C(5) site. We further show that the reaction regioselectivity is independent of the substitution patterns on the aryl moiety. Next, we highlight the keywords role of the proton transfer along the reaction pathway of the title reactions to allow a successful connection between two energetically lower regions along the PES: an electrophilically activated ring-opening step followed by the favored 5-exo-trig cyclization. Additionally, we show that this 5-exo-trig cyclization step is the rate determining step. Finally the tether strain and steric effects present in the rate determining TS structure are evaluated by means of the distortion/interaction model.},
keywords = {aryne distortions, electrophilicity, methylhydrazine, rearrangement, regioselectivities, rules},
pubstate = {published},
tppubtype = {article}
}

@article{RN272,
title = {Quantitative Characterization of the Global Philicity Patterns of Common Diene/Dienophile Pairs in Cycloaddition Reactions Ii: The Interacting Pair Model},
author = { C. Perez-Mendez and R. Contreras},
url = {/brokenurl#<Go to ISI>://WOS:000351790700004},
doi = {10.1016/j.tetlet.2015.01.199},
issn = {0040-4039},
year = {2015},
date = {2015-01-01},
journal = {Tetrahedron Letters},
volume = {56},
number = {14},
pages = {1767-1770},
publisher = {2015 Elsevier Ltd.},
abstract = {We present a unified model of electrophilicity and nucleophilicity that considers the electrophile/nucleophile pair in an interacting regime, thereby avoiding the arbitrariness of defining them as the opposite ends of a unique reactivity scale. The model is validated against rate coefficients for the cycloaddition of azomethine ylides towards substituted acetylenes and Michael addition of a series of 1-(X-substituted pheny1)-2-propyn-1-ones towards hydrazine.},
keywords = {amines, charge cycloaddition, diels-alder electronegativity, electrophilicity, hardness, mechanism, michael nucleophilicity, reactions, reactivity},
pubstate = {published},
tppubtype = {article}
}

@article{RN214,
title = {On-Water Reactivity and Regioselectivity of Quinones in C-N Coupling with Amines: Experimental and Theoretical Study},
author = { M. Martinez-Cifuentes and G. Clavijo-Allancan and C. Di Vaggio-Conejeros and B. Weiss-Lopez and R. Araya-Maturana},
url = {/brokenurl#<Go to ISI>://WOS:000335560100006},
doi = {10.1071/Ch13355},
issn = {0004-9425},
year = {2014},
date = {2014-01-01},
journal = {Australian Journal of Chemistry},
volume = {67},
number = {2},
pages = {217-224},
abstract = {A study about the oxidative coupling of some representative carbo- and heterocyclic non-symmetrical quinones with aryl- and alkylamines, was carried out comparing dichloromethane and water as reaction mediums. We found that the on-water reactions gave better or, at worst, the same results as a conventional organic medium like dichloromethane. Descriptors derived from conceptual density functional theory and approaches of electrostatic nature, such as the molecular electrostatic potential, were used to explain the observed chemical reactivity and regioselectivity. Further, the on-water conditions were used to obtain 24 new aminoquinones with potential biological activity.},
keywords = {addition, alkaloids conjugate derivatives, electrophilicity, green nucleophilicity, potentials, protocol},
pubstate = {published},
tppubtype = {article}
}

@article{RN107,
title = {A Local Extension of the Electrophilicity Index Concept},
author = { A. Cedillo and R. Contreras},
url = {/brokenurl#<Go to ISI>://WOS:000311506100005},
issn = {1870-249x},
year = {2012},
date = {2012-01-01},
journal = {Journal of the Mexican Chemical Society},
volume = {56},
number = {3},
pages = {257-260},
abstract = {A local measure of the electrophilicity has been recently proposed to analyze the chemical reactivity of several kinds of molecules. In this work a theoretical rationalization of the local extension is proposed following the quantitative definition of the molecular electrophilic power and a variational method for the distribution of the transferred charge. A condensation scheme to atoms or fragments follows from its relation to the Fukui function and the local softness. Differences between these quantities are discussed and they are tested in a model system. The analysis shows that the local electrophilicity is more appropriate to describe differences among a set of substituted molecules.},
keywords = {chemical chemical-reactivity, concept, density density-functional descriptors, electrophilicity, fukui function, functional hardness, intermolecular local parameter philicity reactivity, selectivity, softness, theory},
pubstate = {published},
tppubtype = {article}
}