Bridge-Chlorinated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F19%3A00503719" target="_blank" >RIV/61388963:_____/19:00503719 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/19:10393764

Výsledek na webu

<a href="https://pubs.acs.org/doi/10.1021/acs.joc.8b02780" target="_blank" >https://pubs.acs.org/doi/10.1021/acs.joc.8b02780</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.joc.8b02780" target="_blank" >10.1021/acs.joc.8b02780</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Bridge-Chlorinated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids

Popis výsledku v původním jazyce

Radical chlorination of bicyclo[1.1.1]pentane-1,3-dicarboxylic acid is highly selective, and up to four chlorine atoms can be introduced relatively easily without damage to the strained bicyclic cage. Combined with hydrodechlorination with TMS3SiH, direct chlorination provides access to five of the 15 possible chlorinated diacids. Their configuration has been established by X-ray diffraction. Their pKa values have been measured by capillary electrophoresis and calculated at the B3LYP-D3BJ/6-311+G(d,p)-level. The results are in good agreement and reflect the expected trend, from 2.78 +/- 0.08 and 4.14 +/- 0.10 in the parent to 1.07 +/- 0.03 and 2.31 +/- 0.03 in the tetrachlorinated diacid. Strain energy relative to the parent diacid was calculated for all 15 chlorinated diacids and shows a dramatic increase with successive chlorination, due to nonbonded Cl-Cl repulsions.

Název v anglickém jazyce

Bridge-Chlorinated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids

Popis výsledku anglicky

Radical chlorination of bicyclo[1.1.1]pentane-1,3-dicarboxylic acid is highly selective, and up to four chlorine atoms can be introduced relatively easily without damage to the strained bicyclic cage. Combined with hydrodechlorination with TMS3SiH, direct chlorination provides access to five of the 15 possible chlorinated diacids. Their configuration has been established by X-ray diffraction. Their pKa values have been measured by capillary electrophoresis and calculated at the B3LYP-D3BJ/6-311+G(d,p)-level. The results are in good agreement and reflect the expected trend, from 2.78 +/- 0.08 and 4.14 +/- 0.10 in the parent to 1.07 +/- 0.03 and 2.31 +/- 0.03 in the tetrachlorinated diacid. Strain energy relative to the parent diacid was calculated for all 15 chlorinated diacids and shows a dramatic increase with successive chlorination, due to nonbonded Cl-Cl repulsions.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2019

Kód důvěrnosti údajů

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

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

—

Svazek periodika

84

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

14

Strana od-do

2448-2461

Kód UT WoS článku

000460491600007

EID výsledku v databázi Scopus

2-s2.0-85061928147