Substituent Effects of the Alkyl Groups: Polarity vs. Polarizability

Result code in 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>

Alternative codes found

RIV/61388963:_____/07:00087596

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Substituent Effects of the Alkyl Groups: Polarity vs. Polarizability

Original language description

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

Czech name

Substituent Effects of the Alkyl Groups: Polarity vs. Polarizability

Czech description

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

Type

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

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

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Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2007

Confidentiality

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

Name of the periodical

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Volume of the periodical

2007

Issue of the periodical within the volume

17

Country of publishing house

DE - GERMANY

Number of pages

7

Pages from-to

2870-2876

UT code for WoS article

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EID of the result in the Scopus database

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