Synthesis and characterization of sterically and electrostatically shielded pyrrolidine nitroxide radicals

被引：7

作者：

Lampp, Lisa ^{[1
]}

Morgenstern, Uwe ^{[2
]}

Merzweiler, Kurt ^{[2
]}

Imming, Peter ^{[1
]}

Seidel, Ruediger W. ^{[1
]}

机构：

[1] Martin Luther Univ Halle Wittenberg, Inst Pharm, Wolfgang Langenbeck Str 4, D-06120 Halle, Saale, Germany

[2] Martin Luther Univ Halle Wittenberg, Inst Chem, Kurt Mothes Str 2, D-06120 Halle, Saale, Germany

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2019年 / 1182卷

关键词：

Spin label; Nitroxide; Radical; Crystal structure; EPR spectroscopy; EPR SPECTROSCOPY; SPIN LABELS; REDUCTION; PATTERNS;

D O I：

10.1016/j.molstruc.2019.01.015

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Two new pyrrolidine nitroxide radicals, cisgrans-2,5-bis(carboxymethyl)-2,5-diethylpyrrolidine 1-oxyl and 2-(carboxymethyl)-2,5,5-triethylpyrrolidine 1-oxyl, for potential applications as spin probes and labels are reported. Carboxymethyl and ethyl groups have been introduced in the a-positions of the nitroxide group in order to improve the stability of the radicals through steric and electrostatic shielding. The compounds were structurally characterized by X-ray crystallography and EPR spectroscopy. An ascorbic acid reduction assay proves that the newly synthesized radicals exhibit higher reductive stability than the well-known and commercially available nitroxide radicals 3-carboxy-PROXYL and 4-carboxy-TEMPO. (C) 2019 Elsevier B.V. All rights reserved.

引用

页码：87 / 94

页数：8

共 41 条

[1]

[Anonymous], 1976, SPIN LABELING THEORY

[2] Amberlyst A-27, an efficient heterogeneous catalyst for the Michael reaction of nitroalkanes with beta-substituted alkene acceptors [J].