Exploring reversible reactions between CO2 and amines

被引：146

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

共 43 条

[1] Temperature sensitivity of an optical fibre carbon dioxide pressure sensor [J].

Alayli, Y ;

Bendamardji, S .

EUROPEAN PHYSICAL JOURNAL-APPLIED PHYSICS, 1998, 1 (03) :353-360

[2] Isolation and structural determination of two derivatives of the elusive carbamic acid [J].

Aresta, M ;

Ballivet-Tkatchenko, D ;

Dell'Amico, DB ;

Bonnet, MC ;

Boschi, D ;

Calderazzo, F ;

Faure, RE ;

Labella, L ;

Marchetti, F .

CHEMICAL COMMUNICATIONS, 2000, (13) :1099-1100

[3] ROLE OF THE MACROCYCLIC POLYETHER IN THE SYNTHESIS OF N-ALKYLCARBAMATE ESTERS FROM PRIMARY AMINES, CO2 AND ALKYL-HALIDES IN THE PRESENCE OF CROWN-ETHERS [J].

ARESTA, M ;

QUARANTA, E .

TETRAHEDRON, 1992, 48 (08) :1515-1530

[4] CO2 capture by a task-specific ionic liquid [J].

Bates, ED ;

Mayton, RD ;

Ntai, I ;

Davis, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) :926-927

[5] Mitigation of atmospheric CO2 concentrations by increased carbon sequestration in the soil [J].

Batjes, NH .

BIOLOGY AND FERTILITY OF SOILS, 1998, 27 (03) :230-235

[6] Molecular design of intercalation based sensors .2. Sensing of carbon dioxide in functionalized thin films of copper octanediylbis(phosphonate) [J].

Brousseau, LC ;

Aurentz, DJ ;

Benesi, AJ ;

Mallouk, TE .

ANALYTICAL CHEMISTRY, 1997, 69 (04) :688-694

[7] Synthesis and characterization of gels from polyallylamine and carbon dioxide as gellant [J].

Carretti, E ;

Dei, L ;

Baglioni, P ;

Weiss, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (17) :5121-5129

[8] Global estimates of potential mitigation of greenhouse gas emissions by agriculture [J].

Cole, CV ;

Duxbury, J ;

Freney, J ;

Heinemeyer, O ;

Minami, K ;

Mosier, A ;

Paustian, K ;

Rosenberg, N ;

Sampson, N ;

Sauerbeck, D ;

Zhao, Q .

NUTRIENT CYCLING IN AGROECOSYSTEMS, 1997, 49 (1-3) :221-228

[9] A simple and efficient diastereoselective Strecker synthesis of optically pure α-arylglycines [J].

Dave, RH ;

Hosangadi, BD .

TETRAHEDRON, 1999, 55 (37) :11295-11308

[10] Signaling recognition events with fluorescent sensors and switches [J].

de Silva, AP ;

Gunaratne, HQN ;

Gunnlaugsson, T ;

Huxley, AJM ;

McCoy, CP ;

Rademacher, JT ;

Rice, TE .

CHEMICAL REVIEWS, 1997, 97 (05) :1515-1566

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