Articles producció científica> Química Física i Inorgànica

Quantitative Structure-Activity Relationships for the nucleophilicity of trivalent boron compounds

  • Dades identificatives

    Identificador: imarina:3672242
    Autors:
    García-López D, Cid J, Marqués R, Fernández E, Carbó JJ
    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.
  • Altres:

    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
    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: 2024-09-07
    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
  • Paraules clau:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary,Organic Chemistry
    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
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