Electrostatic Calculation of the Substituent Effect: An Efficient Test on Isolated Molecules

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F03%3A00007889" target="_blank" >RIV/60461373:22310/03:00007889 - isvavai.cz</a>

Alternative codes found

RIV/61388963:_____/03:57030104

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Electrostatic Calculation of the Substituent Effect: An Efficient Test on Isolated Molecules

Original language description

The energy of a disubstituted molecule has often been approximated by simple electrostatic formulas that represent the substituents as poles or dipoles. Herein, we test this approach on a new model system that is more direct and more efficient than testing on acid-base properties. The energies of 27 1,4-derivatives of bicyclo[2.2.2]octane were calculated within the framework of the density functional theory at the B3LYP/6-311+G(d,p) level; interaction of the two substituents was evaluated in terms of isodesmic homodesmotic reactions. This interaction energy, checked previously on some experimental gas-phase acidities, was considered to be accurate and served as reference to test the electrostatic approximation. This approximation works well in the qualitative sense as far as the sign and the order of magnitude are concerned: beginning with the strongest interaction between two poles, a weaker interaction between pole and dipole, and the weakest between two dipoles. However, all the ele

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CF - Physical chemistry and theoretical chemistry

OECD FORD branch

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Project

<a href="/en/project/LN00A032" target="_blank" >LN00A032: Structure and dynamics of complex molecular systems and biomolecules</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2003

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Chemistry - A Europian Journal

ISSN

0947-6539

e-ISSN

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Volume of the periodical

9

Issue of the periodical within the volume

19

Country of publishing house

DE - GERMANY

Number of pages

6

Pages from-to

4718-4723

UT code for WoS article

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EID of the result in the Scopus database

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