Substituent Effects of the Alkyl Groups: Polarity vs. Polarizability

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F07%3A00019324" target="_blank" >RIV/60461373:22340/07:00019324 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/07:00087596

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Substituent Effects of the Alkyl Groups: Polarity vs. Polarizability

Popis výsledku v původním jazyce

Substituents effects of the alkyl groups, both straight-chain and branched, were evaluated by means of model reaction series, each comparing the acidities and basicities of the same or very similar compounds. Four such models wereexamined, one based on known gas-phase experimental data (acidity and basicity of alcohols), the three others on density-functional calculations at the levels B3LYP/6-311++G(2df,2pd)//B3LYP/6-311++G(2df,2pd) or B3LYP/6-311+G(d,p)//B3LYP/6-311+G(d,p): acidity and basicity of 4-substituted bicyclo[2.2.2]octan-1-ols, stability of borate anions compared to the stability of ammonium cations, and acidity of imines compared to the basicity of ketones. In all cases the alkyl groups stabilize both the anions and cations; with straight-chain alkyls the effect is proportional and can be called polarizability effect. However, simple mathematical expression of the polarizability is not correct because the effect on the cations is always stronger than on the anions. Effects

Název v anglickém jazyce

Substituent Effects of the Alkyl Groups: Polarity vs. Polarizability

Popis výsledku anglicky

Substituents effects of the alkyl groups, both straight-chain and branched, were evaluated by means of model reaction series, each comparing the acidities and basicities of the same or very similar compounds. Four such models wereexamined, one based on known gas-phase experimental data (acidity and basicity of alcohols), the three others on density-functional calculations at the levels B3LYP/6-311++G(2df,2pd)//B3LYP/6-311++G(2df,2pd) or B3LYP/6-311+G(d,p)//B3LYP/6-311+G(d,p): acidity and basicity of 4-substituted bicyclo[2.2.2]octan-1-ols, stability of borate anions compared to the stability of ammonium cations, and acidity of imines compared to the basicity of ketones. In all cases the alkyl groups stabilize both the anions and cations; with straight-chain alkyls the effect is proportional and can be called polarizability effect. However, simple mathematical expression of the polarizability is not correct because the effect on the cations is always stronger than on the anions. Effects

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2007

Kód důvěrnosti údajů

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

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Svazek periodika

2007

Číslo periodika v rámci svazku

17

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

7

Strana od-do

2870-2876

Kód UT WoS článku

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EID výsledku v databázi Scopus

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