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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/61388963:_____/08:00313815

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

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

2008

Kód důvěrnosti údajů

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

Název periodika

Organic and Biomolecular Chemistry

ISSN

1477-0520

e-ISSN

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Svazek periodika

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Číslo periodika v rámci svazku

6

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

5

Strana od-do

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Kód UT WoS článku

000253909000022

EID výsledku v databázi Scopus

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