Electrochemical and Spectrometric Study of Reactivity of Orthophthalaldehyde with Hydroxylamine: Mechanistic Considerations

0545585 - ÚFCH JH 2022 RIV DE eng J - Journal Article
Donkeng-Dazie, J. - Urban, Jiří - Ludvík, Jiří
Electrochemical and Spectrometric Study of Reactivity of Orthophthalaldehyde with Hydroxylamine: Mechanistic Considerations.
ChemistrySelect. Roč. 6, č. 20 (2021), s. 4881-4888. ISSN 2365-6549. E-ISSN 2365-6549
Institutional support: RVO:61388955
Keywords : ortho-phthalaldehyde * amino-acids * glutaraldehyde * derivatives * Electrochemistry * Hydroxylamine * Orthophthalaldehyde * Reaction mechanisms * 1h-2 * 3-benzoxazin-1-ol
OECD category: Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)
Impact factor: 2.307, year: 2021
Method of publishing: Limited access

Orthophthalaldehyde (o-phthalaldehyde, OPA) is a broadly used biologically, synthetically and analytically significant compound. Its properties are connected with its reactivity towards nucleophiles, namely amines in aqueous mostly basic solutions. Since the reaction mechanisms of OPA and amine condensation are complicated, strongly depending on the amine structure and, therefore, a systematic study of this kind of reaction is presented. Structure activity relationships based on amine structure and their application in reaction optimization are reported. The present paper deals with reaction of OPA with hydroxylamine which is monitored electrochemically and spectrometrically. The mechanism was formulated on the basis of detailed analysis of electrochemical behavior, of the interception of the intermediate (phthalaldehyde mono-oxime) and of the isolation and identification of the main product (1H-2,3-benzoxazin-1-ol).
Permanent Link: http://hdl.handle.net/11104/0322265