Synthesis, characterization and thermal properties of new aromatic quaternary ammonium bromides: precursors for ionic liquids and complexation studies

Journal Article · Fri Oct 01 00:00:00 EDT 2004 · Journal of Solid State Chemistry

DOI:https://doi.org/10.1016/j.jssc.2004.06.046· OSTI ID:20653396

Busi, Sara ^[1]; Lahtinen, Manu ^[1]; Ropponen, Jarmo ^[1]; Valkonen, Jussi ^[1]; Rissanen, Kari ^[1]

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1. Department of Chemistry, University of Jyvaeskylae, P.O. Box 35, 40014 Jyvaeskylae (Finland)

Series of new aromatic R{sub 2}R'{sub 2}N{sup +}Br{sup -} (R=benzyl, 4-methylbenzyl, 2-phenylethyl, 3-phenylpropyl; R'=ethyl, methyl, isopropyl) or RR'{sub 2}NH{sup +}Br{sup -}-type (R=benzyl, R'=isopropyl) quaternary ammonium bromides were prepared by using novel synthetic route in which a formamide (N,N-diethylformamide, N,N-dimethylformamide, N,N-diisopropylformamide) is treated with aralkyl halide in presence of a weak base. The compounds were characterized by {sup 1}H-NMR and {sup 13}C-NMR spectroscopy and mass spectrometry. Structures of the crystalline compounds were determined by X-ray single crystal diffraction, and in addition the powder diffraction method was used to study the structural similarities between the single crystal and microcrystalline bulk material. Three of the compounds crystallized in monoclinic, two in orthorhombic and one in triclinic crystal system, showing ion pairs, which are interconnected by weak hydrogen bonds and weak {pi}-{pi} interactions between the phenyl rings. Three of the compounds appeared as viscous oil or waxes. Finally, TG/DTA and DSC methods were used to analyze thermal properties of the prepared compounds. The lowest melting points were obtained for diethyldi-(2-phenylethyl)ammonium bromide (122.2{sup o}C) and for diethyldi-(3-phenylpropyl)-ammonium bromide (109.1{sup o}C). In general, decomposition of the compounds started at 170-190{sup o}C without identifiable cleavages, thus liquid ranges of 30-70{sup o}C were observed for some of the compounds.

• OSTI ID: 20653396
• Journal Information: Journal of Solid State Chemistry, Vol. 177, Issue 10; Other Information: DOI: 10.1016/j.jssc.2004.06.046; PII: S0022-4596(04)00354-8; Copyright (c) 2004 Elsevier Science B.V., Amsterdam, The Netherlands, All rights reserved; Country of input: International Atomic Energy Agency (IAEA); ISSN 0022-4596
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
AMMONIUM HALIDES
BROMIDES
BROMINE IONS
CALORIMETRY
CARBON 13
DIFFERENTIAL THERMAL ANALYSIS
DIFFRACTION METHODS
HYDROGEN 1
ION PAIRS
LIQUIDS
MASS SPECTROSCOPY
MELTING POINTS
MONOCLINIC LATTICES
MONOCRYSTALS
NUCLEAR MAGNETIC RESONANCE
TEMPERATURE RANGE 0400-1000 K
WEAK INTERACTIONS
X-RAY DIFFRACTION