Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study

Ab initio calculations with complete geometry optimization are reported for monomeric Z- and E-2-methoxy-1-iodo-1-lithio-2-phenyl-1-alkenes. All the stationary points are true local minima on the energy surfaces. The structural data of the lithioalkenes show clear-cut evidence for the Li-Phenyl inte...

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Autores: Barluenga, J. [0000-0002-6474-7782], González, J.M. [0000-0002-7869-9873], Llorente, I., Campos, P.J. [0000-0002-8917-0318], Rodríguez, M.A. [0000-0003-0123-9905], Thiel, W. [0000-0001-6780-0350]
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:1997
País:España
Institución:Universidad de La Rioja (UR)
Repositorio:RIUR. Repositorio Institucional de la Universidad de La Rioja
OAI Identifier:oai:portal.dialnet.es:doc/5bbc68cbb750603269e80fac
Acceso en línea:https://investigacion.unirioja.es/documentos/5bbc68cbb750603269e80fac
Access Level:acceso abierto
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spelling Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio studyBarluenga, J. [0000-0002-6474-7782]González, J.M. [0000-0002-7869-9873]Llorente, I.Campos, P.J. [0000-0002-8917-0318]Rodríguez, M.A. [0000-0003-0123-9905]Thiel, W. [0000-0001-6780-0350]Ab initio calculations with complete geometry optimization are reported for monomeric Z- and E-2-methoxy-1-iodo-1-lithio-2-phenyl-1-alkenes. All the stationary points are true local minima on the energy surfaces. The structural data of the lithioalkenes show clear-cut evidence for the Li-Phenyl interaction in Z-isomer and the Li-O chelation in E-isomer in gas-phase. Based on the ab initio energies, Li-Phenyl interaction should be less relevant than Li,O chelation. Both effects are absent when coordination by solvent (water) is accounted. Inclusion of solvation by solvent continuum model (IPCM) seems essential to rationalize the experimental results. © 1997 Elsevier Science S.A.1997info:eu-repo/semantics/articleSubtype: Articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://investigacion.unirioja.es/documentos/5bbc68cbb750603269e80facreponame:RIUR. Repositorio Institucional de la Universidad de La Riojainstname:Universidad de La Rioja (UR)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1016/S0022-328X(97)00403-8info:eu-repo/semantics/altIdentifier/wos/WOS:000071575400010info:eu-repo/semantics/altIdentifier/pissn/0022-328XTheoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study, 1997, vol. 548, núm. 2, pág. 185-189info:eu-repo/semantics/openAccessoai:portal.dialnet.es:doc/5bbc68cbb750603269e80fac2026-06-14T12:47:17Z
dc.title.none.fl_str_mv Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study
title Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study
spellingShingle Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study
Barluenga, J. [0000-0002-6474-7782]
title_short Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study
title_full Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study
title_fullStr Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study
title_full_unstemmed Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study
title_sort Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study
dc.creator.none.fl_str_mv Barluenga, J. [0000-0002-6474-7782]
González, J.M. [0000-0002-7869-9873]
Llorente, I.
Campos, P.J. [0000-0002-8917-0318]
Rodríguez, M.A. [0000-0003-0123-9905]
Thiel, W. [0000-0001-6780-0350]
author Barluenga, J. [0000-0002-6474-7782]
author_facet Barluenga, J. [0000-0002-6474-7782]
González, J.M. [0000-0002-7869-9873]
Llorente, I.
Campos, P.J. [0000-0002-8917-0318]
Rodríguez, M.A. [0000-0003-0123-9905]
Thiel, W. [0000-0001-6780-0350]
author_role author
author2 González, J.M. [0000-0002-7869-9873]
Llorente, I.
Campos, P.J. [0000-0002-8917-0318]
Rodríguez, M.A. [0000-0003-0123-9905]
Thiel, W. [0000-0001-6780-0350]
author2_role author
author
author
author
author
description Ab initio calculations with complete geometry optimization are reported for monomeric Z- and E-2-methoxy-1-iodo-1-lithio-2-phenyl-1-alkenes. All the stationary points are true local minima on the energy surfaces. The structural data of the lithioalkenes show clear-cut evidence for the Li-Phenyl interaction in Z-isomer and the Li-O chelation in E-isomer in gas-phase. Based on the ab initio energies, Li-Phenyl interaction should be less relevant than Li,O chelation. Both effects are absent when coordination by solvent (water) is accounted. Inclusion of solvation by solvent continuum model (IPCM) seems essential to rationalize the experimental results. © 1997 Elsevier Science S.A.
publishDate 1997
dc.date.none.fl_str_mv 1997
dc.type.none.fl_str_mv info:eu-repo/semantics/article
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info:eu-repo/semantics/publishedVersion
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dc.identifier.none.fl_str_mv https://investigacion.unirioja.es/documentos/5bbc68cbb750603269e80fac
url https://investigacion.unirioja.es/documentos/5bbc68cbb750603269e80fac
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/S0022-328X(97)00403-8
info:eu-repo/semantics/altIdentifier/wos/WOS:000071575400010
info:eu-repo/semantics/altIdentifier/pissn/0022-328X
Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study, 1997, vol. 548, núm. 2, pág. 185-189
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
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instname:Universidad de La Rioja (UR)
instname_str Universidad de La Rioja (UR)
reponame_str RIUR. Repositorio Institucional de la Universidad de La Rioja
collection RIUR. Repositorio Institucional de la Universidad de La Rioja
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