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The Dissociation Constants of Diprotonated Chalcogenobispyridines: Transmission of Electronic Effects Across Chalcogen Bridges
Mälardalen University, Department of Biology and Chemical Engineering.
Mälardalen University, Department of Biology and Chemical Engineering.
2011 (English)In: Journal of Heterocyclic Chemistry, ISSN 0022-152X, Vol. 48, no 4, 868-871 p.Article in journal (Refereed) Published
Abstract [en]

The dissociation constants of the diprotonated chalcogenobispyridines have been determined using potentiometric titrations to establish a method for the measurement of the ability of a bridging ligand to relay electronic effects. The relationship between pK(a) and structure of the chalcogenobispyridines results from a balance between inductive, mesomeric, and steric effects. Delocalization of cationic charge onto the bridgehead increases the apparent electronegativity of the bridging atom, thereby relaying a strong base-weakening effect to the site of first deprotonation. Such delocalization was found to be a function of both the substitution site (4-X > 2-X >> 3-X) and orbital overlap requirements (S > O approximate to Se > Te).

Place, publisher, year, edition, pages
2011. Vol. 48, no 4, 868-871 p.
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Natural Sciences
Identifiers
URN: urn:nbn:se:mdh:diva-15546DOI: 10.1002/jhet.651ISI: 000293745900020Scopus ID: 2-s2.0-79960775554OAI: oai:DiVA.org:mdh-15546DiVA: diva2:562281
Available from: 2012-10-23 Created: 2012-10-10 Last updated: 2012-10-23Bibliographically approved

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