Stability study of alpha-bromophenylacetic acid: Does it represent an appropriate model analyte for chiral separations?
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F20%3A10417604" target="_blank" >RIV/00216208:11160/20:10417604 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=N3bUBl-j0W" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=N3bUBl-j0W</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/elps.202000088" target="_blank" >10.1002/elps.202000088</a>
Alternative languages
Result language
angličtina
Original language name
Stability study of alpha-bromophenylacetic acid: Does it represent an appropriate model analyte for chiral separations?
Original language description
The stability of alpha-bromophenylacetic acid (BPAA) in 50% aqueous methanol solution has been tested. CE in different running buffers was used to separate BPAA from the decomposition reaction products alpha-hydroxyphenylacetic (mandelic) acid and alpha-methoxyphenylacetic acid. Suitable CE separation of all three compounds and other product, bromide, was achieved in 60 mmol/L formate buffer (pH 3.0) at -30 kV in 50 mu m (i.d.) poly(vinyl alcohol)-coated fused silica capillary (30 cm/24.5 cm) with UV detection at 200 nm. The CE method was applied to determine the reaction order of the decomposition of BPAA (0.47 mmol/L) via nucleophilic substitution in 50% aqueous methanol. The first-order reaction kinetics was confirmed by linear and non-linear regression, giving the rate constants 1.52 x 10(-4) +/- 2.76 x 10(-5)s(-1)and 7.89 x 10(-5) +/- 5.02 x 10(-6)s(-1), respectively. Additionally, the degradation products were identified by CE coupled to mass spectrometric (MS) detection. The CE-MS experiments carried out in 60 mmol/L formate buffer (pH 3.0) and in 60 mmol/L acetate buffer (pH 5.0) confirmed the results obtained by CE-UV. Furthermore, the stability of BPAA in polar solvents was tested by(1)H NMR experiments. Our results provide strong evidence of the instability and fast degradation of BPAA in 50% aqueous methanol indicating that BPAA is not suitable as the model analyte for chiral separations.
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
30104 - Pharmacology and pharmacy
Result continuities
Project
<a href="/en/project/EF15_003%2F0000465" target="_blank" >EF15_003/0000465: Establishment of Specialized Team for Advanced Research on Separation Science</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Electrophoresis
ISSN
0173-0835
e-ISSN
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Volume of the periodical
41
Issue of the periodical within the volume
18-19
Country of publishing house
DE - GERMANY
Number of pages
7
Pages from-to
1557-1563
UT code for WoS article
000552293700001
EID of the result in the Scopus database
2-s2.0-85088513907