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

[21] Dendrimer liquid membranes:: CO2 separation from gas mixtures [J].

Kovvali, AS ;

Sirkar, KK .

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2001, 40 (11) :2502-2511

[22] Supercritical carbon dioxide as a green reaction medium for catalysis [J].

Leitner, W .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :746-756

[23] CARBON-DIOXIDE AS A PHOSGENE REPLACEMENT - SYNTHESIS AND MECHANISTIC STUDIES OF URETHANES FROM AMINES, CO2, AND ALKYL CHLORIDES [J].

MCGHEE, W ;

RILEY, D ;

CHRIST, K ;

PAN, Y ;

PARNAS, B .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2820-2830

[24] Catheter-Type sensor for potentiometric monitoring of oxygen, pH and carbon dioxide [J].

Meruva, RK ;

Meyerhoff, ME .

BIOSENSORS & BIOELECTRONICS, 1998, 13 (02) :201-212

[25] TUNING COLOURIMETRIC AND FLUOROMETRIC GAS SENSORS FOR CARBON-DIOXIDE [J].

MILLS, A ;

CHANG, Q .

ANALYTICA CHIMICA ACTA, 1994, 285 (1-2) :113-123

[26] 1H, 13C, 15N NMR and theoretical study of protonated carbamic acids and related compounds [J].

Olah, GA ;

Heiner, T ;

Rasul, G ;

Prakash, GKS .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7993-7998

[27] Kinetics and mechanism of the reversible dissociation of ammonium carbamate: Involvement of carbamic acid [J].

Ramachandran, BR ;

Halpern, AM ;

Glendening, ED .

JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (22) :3934-3941

[28] KINETICS OF REACTION BETWEEN CARBON-DIOXIDE AND ETHYLENEDIAMINE IN NONAQUEOUS SOLVENTS [J].

SADA, E ;

KUMAZAWA, H ;

HAN, ZQ .

CHEMICAL ENGINEERING JOURNAL AND THE BIOCHEMICAL ENGINEERING JOURNAL, 1985, 31 (02) :109-115

[29] Efficient carbamate synthesis via a three-component coupling of an amine, CO2, and alkyl halides in the presence of Cs2CO3 and tetrabutylammonium iodide [J].

Salvatore, RN ;

Shin, SI ;

Nagle, AS ;

Jung, KW .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :1035-1037

[30] Recent patterns and mechanisms of carbon exchange by terrestrial ecosystems [J].

Schimel, DS ;

House, JI ;

Hibbard, KA ;

Bousquet, P ;

Ciais, P ;

Peylin, P ;

Braswell, BH ;

Apps, MJ ;

Baker, D ;

Bondeau, A ;

Canadell, J ;

Churkina, G ;

Cramer, W ;

Denning, AS ;

Field, CB ;

Friedlingstein, P ;

Goodale, C ;

Heimann, M ;

Houghton, RA ;

Melillo, JM ;

Moore, B ;

Murdiyarso, D ;

Noble, I ;

Pacala, SW ;

Prentice, IC ;

Raupach, MR ;

Rayner, PJ ;

Scholes, RJ ;

Steffen, WL ;

Wirth, C .

NATURE, 2001, 414 (6860) :169-172

← 1 2 3 4 5 →