Autor segons l'article: García-López D, Cid J, Marqués R, Fernández E, Carbó JJ
Departament: Química Física i Inorgànica
e-ISSN: 1521-3765
Autor/s de la URV: Carbó Martin, Jorge Juan / Fernández Gutiérrez, Maria Elena
Paraules clau: Affordable and clean energy
Resum: We describe herein the development of quantitative structure-activity relationships (QSAR) for the nucleophilicity of trivalent boron compounds covering boryl fragments bonded to alkali and alkaline-earth metals, to transition metals, and to sp3 boron units in diboron reagents. We used the charge of the boryl fragment (q[B]) and the boron p/s population ratio (p/s) to describe the electronic structures of boryl moieties, whereas the distance-weighted volume (Vw ) descriptor was used to evaluate the steric effects. The three-term easy-to-interpret QSAR model showed statistical significance and predictive ability (r2 =0.88, q2 =0.83). The use of chemically meaningful descriptors has allowed identification of the factors governing the boron nucleophilicity and indicates that the most efficient nucleophiles are those with enhanced the polarization of the B-X bond towards the boron atom and reduced steric bulk. A detailed analysis of the potential energy surfaces of different types of boron substituents has provided insight into the mechanism and established an order of nucleophilicity for boron in B-X: X=Li>Cu>B(sp3 )>Pd. Finally, we used the QSAR model to make a priori predictions of experimentally untested compounds.
Àrees temàtiques: Química Organic chemistry Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biotecnología Biodiversidade Astronomia / física
Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
Adreça de correu electrònic de l'autor: j.carbo@urv.cat mariaelena.fernandez@urv.cat
Identificador de l'autor: 0000-0002-3945-6721 0000-0001-9025-1791
Data d'alta del registre: 2024-11-16
Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
Enllaç font original: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201605798
URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
Referència a l'article segons font original: Chemistry-A European Journal. 23 (21): 5066-5075
Referència de l'ítem segons les normes APA: García-López D, Cid J, Marqués R, Fernández E, Carbó JJ (2017). Quantitative Structure-Activity Relationships for the nucleophilicity of trivalent boron compounds. Chemistry-A European Journal, 23(21), 5066-5075. DOI: 10.1002/chem.201605798
DOI de l'article: 10.1002/chem.201605798
Entitat: Universitat Rovira i Virgili
Any de publicació de la revista: 2017
Tipus de publicació: Journal Publications