Bridge-Chlorinated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids
The result's identifiers
Result code in 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>
Alternative codes found
RIV/00216208:11310/19:10393764
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Bridge-Chlorinated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
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Volume of the periodical
84
Issue of the periodical within the volume
5
Country of publishing house
US - UNITED STATES
Number of pages
14
Pages from-to
2448-2461
UT code for WoS article
000460491600007
EID of the result in the Scopus database
2-s2.0-85061928147