Steric effects of polar substituents evaluated in terms of energy by means of isodesmic reactions

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F08%3A00020410" target="_blank" >RIV/60461373:22310/08:00020410 - isvavai.cz</a>

Alternative codes found

RIV/61388963:_____/08:00313815

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 polar substituents evaluated in terms of energy by means of isodesmic reactions

Original language description

Steric effects of various polar and some charged groups were estimated on sterically crowded cyclopropane cis-1,2-bisderivatives 2 or 3, in which the variable substituent is in the proximity of a t-butyl group or of a methyl group. The steric energy wasevaluated with reference to the pertinent mono derivatives, that is as reaction energy of an isodesmic reaction, in which the crowded compound is formally synthesized from simple derivatives. Energies were calculated within the framework of the density functional theory at level B3LYP/6-311+G(d,p)//B3LYP/6-311+G(d,p) for 11 dipolar and 5 charged substituents. Interaction of charged substituents is not only steric (destabilizing) but also inductive (stabilizing). The steric effects evaluated in this waydiffer distinctly from the standard steric constants derived purely from the van der Waals radii of the substituents.

Czech name

Steric effects of polar substituents evaluated in terms of energy by means of isodesmic reactions

Czech description

Steric effects of various polar and some charged groups were estimated on sterically crowded cyclopropane cis-1,2-bisderivatives 2 or 3, in which the variable substituent is in the proximity of a t-butyl group or of a methyl group. The steric energy wasevaluated with reference to the pertinent mono derivatives, that is as reaction energy of an isodesmic reaction, in which the crowded compound is formally synthesized from simple derivatives. Energies were calculated within the framework of the density functional theory at level B3LYP/6-311+G(d,p)//B3LYP/6-311+G(d,p) for 11 dipolar and 5 charged substituents. Interaction of charged substituents is not only steric (destabilizing) but also inductive (stabilizing). The steric effects evaluated in this waydiffer distinctly from the standard steric constants derived purely from the van der Waals radii of the substituents.

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

2008

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

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Issue of the periodical within the volume

6

Country of publishing house

GB - UNITED KINGDOM

Number of pages

5

Pages from-to

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UT code for WoS article

000253909000022

EID of the result in the Scopus database

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