Reductive amination of glutaraldehyde 2,4-dinitrophenylhydrazone using 2-picoline borane and high-performance liquid chromatographic analysis
| Autor: | Hideki Nakagome, Akiko Ohno, Naoki Kunugita, Shigehisa Uchiyama, Yohei Inaba, Hironari Sakamoto |
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| Rok vydání: | 2012 |
| Předmět: |
chemistry.chemical_classification
Chromatography Double bond Hydrazones Borane Biochemistry Reductive amination Analytical Chemistry chemistry.chemical_compound chemistry Glutaral Amide Electrochemistry Environmental Chemistry Single bond Acetonitrile Chromatography High Pressure Liquid Spectroscopy Cis–trans isomerism Amination |
| Zdroj: | The Analyst. 137:4274 |
| ISSN: | 1364-5528 0003-2654 |
| DOI: | 10.1039/c2an35230c |
| Popis: | A typical method for the measurement of glutaraldehyde (GLA) employs 2,4-dinitrophenylhydrazine (DNPH) to form GLA-DNPhydrazone derivatives. However, this method is subject to analytical errors because GLA-DNPhydrazone is a quaternary bis-derivative and forms three geometric isomers (E-E, E-Z and Z-Z) as a result of the two C[double bond, length as m-dash]N double bonds. To overcome this issue, a method for transforming the C[double bond, length as m-dash]N double bond into a C-N single bond, using reductive amination of DNPhydrazone derivatives, has been applied. The amination reaction of GLA-DNPhydrazones with 2-picoline borane is accelerated with catalytic amounts of acid and is completed within 10 minutes in the presence of 100 mmol L(-1) phosphoric acid. Reduction of GLA-DNPhydrazone by 2-picoline borane is unique and results in the formation of N-(2,4-dinitrophenyl)-1-piperidinamine (DNPPA). NMR and LC-APCI-MS data confirmed the product identification. DNPPA is very stable and did not change when stored for at least four weeks at room temperature. DNPPA has excellent solubility of 14.6 g L(-1) at 20 °C in acetonitrile. The absorption maximum wavelength and the molar absorptivity of DNPPA were 351 nm and 4.2 × 10(4) L mol(-1) cm(-1) respectively. Complete separation between the reduced forms of C1-C10 aldehyde DNPhydrazones, including DNPPA, can be achieved by operating the reversed-phase high-performance liquid chromatograph at 351 nm in gradient mode using a C18 amide column. The reductive amination method for GLA overcomes analytical errors caused by E-E, E-Z and Z-Z geometrical isomers. |
| Databáze: | OpenAIRE |
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