Semi-empirical studies of substituent effects on the ionization of bicyclooctane carboxylic acids and quinuclidines

Helena Dies y Riega; Luis Rincón; Rafael Almeida

doi:10.1002/poc.579

Semi-empirical studies of substituent effects on the ionization of bicyclooctane carboxylic acids and quinuclidines

Helena Dies y Riega
, Luis Rincón
, Rafael Almeida^*

^*Corresponding author for this work

Universidad de Los Andes (ULA)

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

Semiempirical AM1 calculations were performed for a representative series of 4-substituted bicyclooctane carboxylic acids and quinuclidines. It was found that the Hammett constant, σ_I, and the Swain and Lupton field constant, F, correlate linearly with the differences in the heat of formation of isodesmic reactions. These constants also correlate with the charges on the acid moiety of the bicyclooctane acids and their anions, and with the hydrogen net charge on the protonated quinuclidines. For all cases, the NO₂ was the poorest correlated substituent.

Original language	English
Pages (from-to)	107-113
Number of pages	7
Journal	Journal of Physical Organic Chemistry
Volume	16
Issue number	2
DOIs	https://doi.org/10.1002/poc.579
State	Published - Feb 2003
Externally published	Yes

Keywords

Bicyclooctane carboxylic acids
Field effects
Inductive effects
Quinuclidines
Substituent effects

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10.1002/poc.579

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title = "Semi-empirical studies of substituent effects on the ionization of bicyclooctane carboxylic acids and quinuclidines",

abstract = "Semiempirical AM1 calculations were performed for a representative series of 4-substituted bicyclooctane carboxylic acids and quinuclidines. It was found that the Hammett constant, σI, and the Swain and Lupton field constant, F, correlate linearly with the differences in the heat of formation of isodesmic reactions. These constants also correlate with the charges on the acid moiety of the bicyclooctane acids and their anions, and with the hydrogen net charge on the protonated quinuclidines. For all cases, the NO2 was the poorest correlated substituent.",

keywords = "Bicyclooctane carboxylic acids, Field effects, Inductive effects, Quinuclidines, Substituent effects",

author = "\{Dies y Riega\}, Helena and Luis Rinc{\'o}n and Rafael Almeida",

year = "2003",

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doi = "10.1002/poc.579",

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journal = "Journal of Physical Organic Chemistry",

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T1 - Semi-empirical studies of substituent effects on the ionization of bicyclooctane carboxylic acids and quinuclidines

AU - Dies y Riega, Helena

AU - Rincón, Luis

AU - Almeida, Rafael

PY - 2003/2

Y1 - 2003/2

N2 - Semiempirical AM1 calculations were performed for a representative series of 4-substituted bicyclooctane carboxylic acids and quinuclidines. It was found that the Hammett constant, σI, and the Swain and Lupton field constant, F, correlate linearly with the differences in the heat of formation of isodesmic reactions. These constants also correlate with the charges on the acid moiety of the bicyclooctane acids and their anions, and with the hydrogen net charge on the protonated quinuclidines. For all cases, the NO2 was the poorest correlated substituent.

AB - Semiempirical AM1 calculations were performed for a representative series of 4-substituted bicyclooctane carboxylic acids and quinuclidines. It was found that the Hammett constant, σI, and the Swain and Lupton field constant, F, correlate linearly with the differences in the heat of formation of isodesmic reactions. These constants also correlate with the charges on the acid moiety of the bicyclooctane acids and their anions, and with the hydrogen net charge on the protonated quinuclidines. For all cases, the NO2 was the poorest correlated substituent.

KW - Bicyclooctane carboxylic acids

KW - Field effects

KW - Inductive effects

KW - Quinuclidines

KW - Substituent effects

UR - https://www.scopus.com/pages/publications/0037322078

U2 - 10.1002/poc.579

DO - 10.1002/poc.579

M3 - Artículo

AN - SCOPUS:0037322078

SN - 0894-3230

VL - 16

SP - 107

EP - 113

JO - Journal of Physical Organic Chemistry

JF - Journal of Physical Organic Chemistry

IS - 2

ER -

Semi-empirical studies of substituent effects on the ionization of bicyclooctane carboxylic acids and quinuclidines

Abstract

Keywords

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