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Role of Substrate Substituents in Alkene Metathesis Mediated by a Ru Alkylidene Catalyst

dc.contributor.authorTobón P
dc.contributor.authorGómez S
dc.contributor.authorRestrepo A
dc.contributor.authorNúñez-Zarur F.
dc.date.accessioned2022-09-14T14:34:01Z
dc.date.available2022-09-14T14:34:01Z
dc.date.created2021
dc.identifier.issn2767333
dc.identifier.urihttp://hdl.handle.net/11407/7556
dc.descriptionQuantum mechanical calculations on the mechanism of olefin metathesis with a variety of substituents mediated by a Ru alkylidene catalyst reveal multistep processes along the general reactants → adduct → coordination complex → metallacycle → decoordination complex → products pathway for two consecutive turnovers. Net energy barriers in solution do not exceed 12 kcal mol-1 during the [Ru]=CHPh + R1R2C=CH2 → [Ru] =CR1R2 + H2C=CHPh first turnover and 20 kcal mol-1 during the [Ru] =CR1R2 + R1R2C=CH2 → [Ru]=CH2 + R1R2C=CR1R2 second turnover. The complex series of steps is initially driven by the evolution of the Ru(catalyst)···C(olefin) contact. Dissection of bonding interactions using the tools provided by the natural bond orbitals and by the quantum theory of atoms in molecules methods indicate that each contact in the Ru(catalyst)···C(catalyst)···C(olefin)···C(olefin)···Ru(catalyst) cyclic reactive center undergoes the following series of transformations in different orders: no interaction → long range → σ → → π. Every single contact in this reactive center gains/loses an entire σ bond during the ···TS → metallacycle → TS··· interval. The lowest point in the potential energy surface is usually the metallacycle. For the first turnover, cycloreversion and final elimination of the products exhibit late transition states leading to higher relative energy barriers. Conversely, for the second turnover, it is the metallacycle to decoordination complex transformation step which leads to the highest barriers, constituting the rate-determining step for the entire process. Each step of the reaction is best described as a highly asynchronous process. Electron-withdrawing groups exhibit the largest overall barriers by virtue of destabilizing the emerging πbond in the final R1R2C=CR1R2 olefin during the second turnover. ©eng
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.isversionofhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-85100148570&doi=10.1021%2facs.organomet.0c00482&partnerID=40&md5=b9dba219b8c29fa953c7098a1494d6f0
dc.sourceOrganometallics
dc.titleRole of Substrate Substituents in Alkene Metathesis Mediated by a Ru Alkylidene Catalyst
dc.typeArticle
dc.rights.accessrightsinfo:eu-repo/semantics/restrictedAccess
dc.publisher.programCiencias Básicas
dc.type.spaArtículo
dc.identifier.doi10.1021/acs.organomet.0c00482
dc.publisher.facultyFacultad de Ciencias Básicas
dc.affiliationTobón, P., Instituto de Química, Universidad de Antioquia UdeA, Calle 70 No. 52-21, Medellín, 50010, Colombia
dc.affiliationGómez, S., Scuola Normale Superiore, Classe di Scienze, Piazza dei Cavalieri 7, Pisa, 56126, Italy
dc.affiliationRestrepo, A., Instituto de Química, Universidad de Antioquia UdeA, Calle 70 No. 52-21, Medellín, 50010, Colombia
dc.affiliationNúñez-Zarur, F., Facultad de Ciencias Básicas, Universidad de Medellín, Carrera 87 No. 30-65, Medellín, 050026, Colombia
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