Analysis of Substituent Effects in Naphthalene Skeleton

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Title:Analysis of Substituent Effects in Naphthalene Skeleton
Creators:
Pařík, Patrik
Ludwig, Miroslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 12, pp. 2297-2314
Uncontrolled Keywords:Naphthalenes, Naphthoic acids, Chemometrics, AISE, Solvent effects, Carboxylic acids, Acidity, Dissociation constants, Substituent effects

Abstract

The dissociation constants of 45 substituted 1- and 2-naphthoic acids in six organic solvents (methanol, ethanol, acetonitrile, dimethylformamide, dimethyl sulfoxide, pyridine) have been used to evaluate the substituent effects in the naphthalene skeleton. The dissociation constants data have been treated traditionally by using Dewar-Grisdale equation and the Taft DSP equation, and the alternative interpretation of substituent effects (AISE) method. Quantitative comparison of substituent effects and their transmission from different positions, combination of inductive and resonance effects from various positions, and effects of solvents are discussed. Best results are predominantly provided by the AISE. Substituent effects are stronger in the case of substituents affecting from ring of the naphthalene skeleton bearing carboxylic group than from ring not bearing carboxylic group, and there are no substantial differences between the individual positions of this ring. The contribution of resonance effects at 4α and 8β positions distinctly changes with the medium. Special quality of substituent H was found in comparison with other substituents presumably due their bulkier character. The principal component analysis (PCA) has been also applied to treat the mean dissociation constants using the single substituent property approach. The dissociation together with reactivity data for other naphthalene derivatives have been tested for comprehensive evaluation using PCA. There was found a large similarity of naphthalene reactivity data tested from the point of view of substituent effects. <p>

Title:Analysis of Substituent Effects in Naphthalene Skeleton
Creators:
Pařík, Patrik
Ludwig, Miroslav
Uncontrolled Keywords:Naphthalenes, Naphthoic acids, Chemometrics, AISE, Solvent effects, Carboxylic acids, Acidity, Dissociation constants, Substituent effects
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:69
Number:12
Page Range:pp. 2297-2314
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20042297UNSPECIFIED
ID Code:2337
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Pařík, Patrik; Ludwig, Miroslav (2004) Analysis of Substituent Effects in Naphthalene Skeleton. Collection of Czechoslovak Chemical Communications, 69 (12). pp. 2297-2314. ISSN 0010-0765

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