Scope and Limitation of the Inductive Effect: Importance of Charged Substituents

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F04%3A00011340" target="_blank" >RIV/60461373:22310/04:00011340 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/04:00100788

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Scope and Limitation of the Inductive Effect: Importance of Charged Substituents

Popis výsledku v původním jazyce

The interaction of two relatively distant charged or dipolar groups was evaluated on 1,4-disubstituted bicyclo[2.2.2]octane derivatives as the reaction energy of the isodesmic-homodesmotic reaction, in which this derivative is formed from two mono derivatives. Energies of the individual compounds were calculated at the B3LYP/6-311+G(d,p) level. All combinations of 12 common substituents were investigated, representing 78 reaction energies in a 12x12 data matrix. The behaviour of charged and dipolar substituents is considerably different. Interaction with a charged group is described precisely (R>0.997) by one parameter, essentially identical with the standard inductive constant I. Interaction of two dipolar substituents depends also on I, but requiresan additional parameter, important particularly in the case of donor substituents (NH2, OH, Cl), less important to insignificant with the others. It is significantly correlated with the electronegativity of the first atom. Alternatively,

Název v anglickém jazyce

Scope and Limitation of the Inductive Effect: Importance of Charged Substituents

Popis výsledku anglicky

The interaction of two relatively distant charged or dipolar groups was evaluated on 1,4-disubstituted bicyclo[2.2.2]octane derivatives as the reaction energy of the isodesmic-homodesmotic reaction, in which this derivative is formed from two mono derivatives. Energies of the individual compounds were calculated at the B3LYP/6-311+G(d,p) level. All combinations of 12 common substituents were investigated, representing 78 reaction energies in a 12x12 data matrix. The behaviour of charged and dipolar substituents is considerably different. Interaction with a charged group is described precisely (R>0.997) by one parameter, essentially identical with the standard inductive constant I. Interaction of two dipolar substituents depends also on I, but requiresan additional parameter, important particularly in the case of donor substituents (NH2, OH, Cl), less important to insignificant with the others. It is significantly correlated with the electronegativity of the first atom. Alternatively,

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CF - Fyzikální chemie a teoretická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/LN00A032" target="_blank" >LN00A032: Struktura a dynamika komplexních molekulových systémů a biomolekul</a><br>

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2004

Kód důvěrnosti údajů

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

Název periodika

Journal of Physical Organic Chemistry

ISSN

0894-3230

e-ISSN

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Svazek periodika

17

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

7

Strana od-do

124-130

Kód UT WoS článku

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EID výsledku v databázi Scopus

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