Steric effects of the alkyl groups: evaluation on isolated molecules by means of isodesmic reactions

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F07%3A00019335" target="_blank" >RIV/60461373:22340/07:00019335 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Steric effects of the alkyl groups: evaluation on isolated molecules by means of isodesmic reactions

Original language description

Several possible scales of steric effects of the alkyl groups were suggested on the basis of isodesmic model reactions, in which a sterically crowded compound is formally synthesized from simpler derivatives. The reaction energies were calculated withinthe framework of the density functional theory at the level B3LYP/6-311+G(d.p)//B3LYP/6-311+G(d.p) for 6 model systems and 7 various alkyl groups. The most important systems were cis-1,2-dialkylcyclopropanes 1 synthesized from two mono derivatives and sterically crowded derivatives of bicyclo[2.2.2]octane 2 with C3 symmetry. The scales of steric effects evaluated from the two models were rather different: the first scale depended in effect only on the C atoms in the and positions and the effects were almost equal for all primary alkyls. The second scale depended also on the position and the effect of the CH2-t-Bu group was much greater than that of the ethyl group. Any relationship between various systems was found rarely, only in the c

Czech name

Steric effects of the alkyl groups: evaluation on isolated molecules by means of isodesmic reactions

Czech description

Several possible scales of steric effects of the alkyl groups were suggested on the basis of isodesmic model reactions, in which a sterically crowded compound is formally synthesized from simpler derivatives. The reaction energies were calculated withinthe framework of the density functional theory at the level B3LYP/6-311+G(d.p)//B3LYP/6-311+G(d.p) for 6 model systems and 7 various alkyl groups. The most important systems were cis-1,2-dialkylcyclopropanes 1 synthesized from two mono derivatives and sterically crowded derivatives of bicyclo[2.2.2]octane 2 with C3 symmetry. The scales of steric effects evaluated from the two models were rather different: the first scale depended in effect only on the C atoms in the and positions and the effects were almost equal for all primary alkyls. The second scale depended also on the position and the effect of the CH2-t-Bu group was much greater than that of the ethyl group. Any relationship between various systems was found rarely, only in the c

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

Organic and Biomolecular Chemistry

ISSN

1477-0520

e-ISSN

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Volume of the periodical

2007

Issue of the periodical within the volume

5

Country of publishing house

GB - UNITED KINGDOM

Number of pages

7

Pages from-to

2081-2086

UT code for WoS article

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EID of the result in the Scopus database

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