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The Dissociation Co...
The Dissociation Constants of Diprotonated Chalcogenobispyridines : Transmission of Electronic Effects Across Chalcogen Bridges
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- Angus-Dunne, Sarah J. (author)
- Mälardalens högskola,Institutionen för biologi och kemiteknik
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- Dunne, Simon J. (author)
- Mälardalens högskola,Institutionen för biologi och kemiteknik
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(creator_code:org_t)
- 2011-04-15
- 2011
- English.
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In: Journal of Heterocyclic Chemistry. - : Wiley. - 0022-152X .- 1943-5193. ; 48:4, s. 868-871
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https://urn.kb.se/re...
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Abstract
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- 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).
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