{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T00:49:07Z","timestamp":1760316547732,"version":"build-2065373602"},"reference-count":80,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2006,12,13]],"date-time":"2006-12-13T00:00:00Z","timestamp":1165968000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2007,3,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A \u0394<jats:italic>G<\/jats:italic><jats:sub>eq<\/jats:sub> stability scale of secondary \u03b1\u2010oxy\u2010organolithium compounds was established from measurements of tin\u2013lithium exchange equilibria in THF, and the quantitative effects of substituents at the anionic center on carbanion stability are presented. A new lead\u2013lithium exchange equilibrium reaction was also investigated and shown to be a very useful alternative for the determination of the relative stability of the more sterically hindered organolithium compounds. Alkyl groups adversely affect the stability of organolithium compounds when attached to the carbon bearing the negative charge, but the extent of this effect is highly dependent on the nature of the rest of the substituents attached to the anionic center. Quantitative data on the stabilization imparted to organolithium compounds by Li\u2013O and Li\u2013N chelation have been determined for a variety of systems. The formation of four\u2010 and five\u2010membered chelate rings leads to a considerable stabilization of the organolithium compound, while chelation through the formation of six\u2010membered rings affords no extra stabilization to this type of organometallics. Multinuclear NMR experiments carried out on several \u03b1\u2010oxy\u2010organolithium compounds to determine their aggregation state are supportive of these species being monomers in THF solution.<\/jats:p>","DOI":"10.1002\/chem.200600864","type":"journal-article","created":{"date-parts":[[2006,12,13]],"date-time":"2006-12-13T05:15:09Z","timestamp":1165986909000},"page":"2277-2289","source":"Crossref","is-referenced-by-count":12,"title":["Quantitative Data on the Effects of Alkyl Substituents and Li\u2013O and Li\u2013N Chelation on the Stability of Secondary \u03b1\u2010Oxy\u2010Organolithium Compounds"],"prefix":"10.1002","volume":"13","author":[{"given":"Pablo","family":"Monje","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Paula","family":"Gra\u00f1a","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"M. Rita","family":"Paleo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"F.\u2005Javier","family":"Sardina","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2007,2,19]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","first-page":"1","volume-title":"Organometallics in Synthesis. A Manual","author":"Schlosser M.","year":"2003"},{"volume-title":"Organolithiums: Selectivity for Synthesis","year":"2002","author":"Clayden J.","key":"e_1_2_6_3_2"},{"volume-title":"Lithium Chemistry. 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