Synthesis of sequentially deuterated 1-n-butyl-3-methylimidazolium ionic liquids

Dublin Core

Título

Synthesis of sequentially deuterated 1-n-butyl-3-methylimidazolium ionic liquids

Tema

LIQUIDOS IONICOS
SINTESIS
BIBLIOGRAFIA NACIONAL QUIMICA
2011

Abstract

Arbitrarily defined as organic salts with melting points below 1001C, ionic liquids (ILs) have gained considerable notoriety in the past decade. Owing to their negligible vapor pressure, thermal stability, and tunable solvent properties, these materials have found applications in a wide range of laboratory and industrial processes.1 As part of efforts aimed at better understanding the liquid structure of imidazolium-based ILs, we have shown that intraionic hydrogen-bonding (H-bonding) interactions in 1-n-butyl-3-methylimidazolium chloride ([C4mim]Cl (1), Figure 1) are evidenced by sizable deuterium isotope effects on the chloride ion 35/37Cl NMR signal (i.e. D35/37Cl(H,D)).2 Measurements obtained on the [C4mim]Cl isotopologues [2-d1]-[C4mim]Cl and [2,4,5-d3]-[C4mim]Cl led to D35/37Cl(H,D) values of up to 2 ppm, and corroborated the presence of H-bonds between the anion and the imidazolium cation protons on the C-2, C-4, and C-5 positions. Recent theoretical studies indicate that H-bonding between the anion and protons along the N-alkyl groups could also have an impact on the structure and dynamics of this class of ILs.3,4 Based on our previous results, these anion–cation interactions could be detected experimentally by measurement of deuterium isotope effects on the 35/37Cl NMR signal of the chloride ion. For this purpose, we decided to synthesize a series of [C4mim]Cl deuterium isotopologues sequentially labeled along the N-alkyl group carbons (Figure 1a–e). These could also be easily converted by metathesis to the corresponding tetrafluoroborate and hexafluorophosphate imidazolium salts (i.e. [C4mim]BF4 and [C4mim]PF6), which would be suitable for the study of interionic H-bonds through analysis of deuterium isotope effects on the 10/11B, 19F, and 31P signals of the BF! 4 and BF! 6 anions. In this manuscript we describe a strategy which uses similar routes to minimize the number of distinct reactions needed to prepare these compounds. As detailed below, good yields after the initial deuterium incorporation reaction were achieved in several cases through the combination of well-established chemical transformations into efficient single-step processes.

Autor

Khrizman, Alexander
Cheng, Hiu Yan

Fuente

Journal of Labelled Compounds and Radiopharmaceuticals v. 54, no. 8. -- p. 401-407

Editor

Wiley & Sons

Fecha

2011

Derechos

Información sobre Derechos de Autor

(Por favor lea este aviso antes de abrir los documentos u objetos)

La legislación uruguaya protege el derecho de autor sobre toda creación literaria, científica o artística, tanto en lo que tiene que ver con sus derechos morales, como en lo referente a los derechos patrimoniales con sujeción a lo establecido por el derecho común y las siguientes leyes

(LEY 9.739 DE 17 DE DICIEMBRE DE 1937 SOBRE PROPIEDAD LITERARIA Y ARTISTICA CON LAS MODIFICACIONES INTRODUCIDAS POR LA LEY DE DERECHO DE AUTOR Y DERECHOS CONEXOS No. 17.616 DE 10 DE ENERO DE 2003, LEY 17.805 DE 26 DE AGOSTO DE 2004, LEY 18.046 DE 24 DE OCTUBRE DE 2006 LEY 18.046 DE 24 DE OCTUBRE DE 2006)

ADVERTENCIA - La consulta de este documento queda condicionada a la aceptación de las siguientes condiciones de uso: Este documento es únicamente para usos privados enmarcados en actividades de investigación y docencia. No se autoriza su reproducción con fines de lucro. Esta reserva de derechos afecta tanto los datos del documento como a sus contenidos. En la utilización o cita de partes debe indicarse el nombre de la persona autora.

Formato

PDF

Idioma

Inglés

Tipo

Artículo

Identificador

DOI: 10.1002/jlcr.1884
Fecha de agregación
September 2, 2013
Colección
Bibliografía Nacional Química
Tipo de Elemento
Document
Etiquetas
,
Citación
Khrizman, Alexander, “Synthesis of sequentially deuterated 1-n-butyl-3-methylimidazolium ionic liquids,” RIQUIM - Repositorio Institucional de la Facultad de Química - UdelaR, accessed November 27, 2020, http://riquim.fq.edu.uy/items/show/870.
Archivos