Exploring reversible reactions between CO2 and amines

被引：144

作者：

Hampe, EM ^{[1
]}

Rudkevich, DM ^{[1
]}

机构：

[1] Univ Texas, Dept Biochem & Chem, Arlington, TX 76019 USA

来源：

TETRAHEDRON | 2003年 / 59卷 / 48期

关键词：

amines; amino acids; carbon dioxide fixation; fluorescence;

D O I：

10.1016/j.tet.2003.09.096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 'old' chemistry between CO2 and primary alkylamines has been revisited. Amines 1 and 2, with appended aromatic fluorophores, reversibly reacted with CO2 in polar aprotic solvent (e.g. DMSO, DMF) with the formation of carbamic acids 3 and 4. As a result, strong fluorescence occurred, thus directly reporting on the CO2 entrapment. Carbamic acids were studied by H-1 and C-13 NMR spectroscopy in DMSO-d(6). The carbamate bond, despite being covalent, is reversible and can be broken upon heating or simply flashing solutions with inert gases. Synthesis and evaluation of a CO2-sensing amino acid-alpha-naphthylglycine 7 is also reported for potential CO2 monitoring under biorelevant conditions in aqueous solutions. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：9619 / 9625

页数：7

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