Electrostatic Effects in Ionization Equilibria: An AM1 Study of Reversed Substituent Effect in 5-Fluorobicyclo[3.3.3]undecane-1-carboxylic Acid

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Title:Electrostatic Effects in Ionization Equilibria: An AM1 Study of Reversed Substituent Effect in 5-Fluorobicyclo[3.3.3]undecane-1-carboxylic Acid
Creators:
Friedl, Zdeněk
Böhm, Stanislav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 7, pp. 1467-1471

Abstract

<p>Relative proton transfer enthalpies δ ∆<i>H</i><sup>0</sup> of <i>sp</i> and <i>ap</i> conformers of 5-fluorobicyclo[3.3.3]undecane-1-carboxylic acid have been calculated by the AM1 method and the results were compared with the prediction of the electrostatic theory. It is shown that the great reversed substituent effect in the sp conformer (δ ∆<i>H</i><sup>0</sup> = 32.1 kJ mol<sup>-1</sup>) is substantially overestimated largely due to sterical Baeyer strain and non-bonded interactions.

Title:Electrostatic Effects in Ionization Equilibria: An AM1 Study of Reversed Substituent Effect in 5-Fluorobicyclo[3.3.3]undecane-1-carboxylic Acid
Creators:
Friedl, Zdeněk
Böhm, Stanislav
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:59
Number:7
Page Range:pp. 1467-1471
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19941467UNSPECIFIED
ID Code:569
Item Type:Article
Deposited On:06 Feb 2009 17:02
Last Modified:06 Feb 2009 16:02

Citation

Friedl, Zdeněk; Böhm, Stanislav (1994) Electrostatic Effects in Ionization Equilibria: An AM1 Study of Reversed Substituent Effect in 5-Fluorobicyclo[3.3.3]undecane-1-carboxylic Acid. Collection of Czechoslovak Chemical Communications, 59 (7). pp. 1467-1471. ISSN 0010-0765

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