Crystal structures of bis(quaternaryammonium bromide) surfactants, ethanediyl-1,2-bis(butyldimethylammonium bromide) dihydrate and propanediyl-1,3-bis(butyldimethylammonium bromide)

Hattori, Norikatsu; Masuda, Hideki; Okabayashi, Hirofumi; O’Connor, Charmian J.

doi:10.1016/s0022-2860(98)00380-9

Cited by 10 publications

(15 citation statements)

References 15 publications

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“…4. The conformation of the cation of this structure resembles (as well as the cations on the following structures 5, 7, and 11) some of the previously reported structures (for example, Cambridge Structural Database (CSD) entry MEHTIC), [48,49] in which the dication is reported to be in trans conformation, although in those structures the Z-conformation is more right-angled compared with that of compound 2. The columnar packing (Fig.…”

Section: X-ray Single Crystal Diffraction Structure Analysissupporting

confidence: 76%

Physicochemical Properties of New Dicationic Ether-Functionalized Low Melting Point Ammonium Salts

et al. 2010

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Eleven new and one previously known but insufficiently characterized dicationic quaternary ammonium (QA) salts were synthesized and characterized. They contain an ethoxy ethyl group either in a side chain and/or as spacer of the diammonium cation and have bromide, hexafluorophosphate (PF − 6 ), bis(trifluoromethanesulfonyl)imide (TFSI), or trifluoromethanesulfonate (TFMS) as an anion. 1 H and 13 C techniques, mass spectrometry, and elemental analysis together with X-ray diffraction and thermoanalytical methods were used for their characterization both in the liquid and solid state. In addition, residual water content and viscosity measurements were made for the two room temperature ionic liquids (RTILs). Capillary electrophoresis was used to measure the conductivity of the RTILs. Crystal structures of four compounds were determined by X-ray single crystal diffraction, and powder diffraction was used to study the crystallinity of the solid salts and to compare the structural similarities between the single crystals and the microcrystalline bulk form. Two of the TFSI salts were liquids below room temperature, having liquid ranges of ∼380 and 350 • C, respectively, and seven out of 12 salts melted below 100 • C. In addition, both the TFSI and PF 6 salts exhibited high thermal stabilities decomposing at about, or above 300 • C. Both RTILs presented moderate viscosities at elevated temperatures. The determined physicochemical properties of the reported ILs suggest their applicability for various applications such as heat transfer fluids, high temperature synthesis, and lubricants.

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Section: X-ray Single Crystal Diffraction Structure Analysissupporting

confidence: 76%

Physicochemical Properties of New Dicationic Ether-Functionalized Low Melting Point Ammonium Salts

et al. 2010

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“…Therefore, crystal structures of the gemini surfactants are very rare. So far, only the crystal structures of bis(quaternaryammonium bromide) surfactants C n -2-C n (n = 4, 12) have been determined by single-crystal X-ray diffraction [22,23].…”

Section: Introductionmentioning

confidence: 99%

Crystalline structures and mesomorphic properties of gemini diammonium surfactants with a pendant hydroxyl group

Wei

Sun

et al. 2011

Journal of Colloid and Interface Science

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“…This is a much higher value than any of those shown in Figure , and hence such a structure is ruled out. In fact, several authors have proposed, on the basis of XRD data, that n -2- n bis-quat gemini in the crystalline lattice have their alkyl tails in a trans conformation with respect to the spacer plane. ,, Jurasin et al have also proposed that the tails interdigitate and pack with a tilt angle with respect to the bromide ion planes Figure implies that there are significant differences in packing according to the spacer length because no regularity in the smectic periodicities is observed.…”

Section: Resultsmentioning

confidence: 99%

Critical Role of the Spacer Length of Gemini Surfactants on the Formation of Ionic Liquid Crystals and Thermotropic Behavior

et al. 2017

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Numerous reports have shown that the self-assembling properties of 12-s-12 bis(quaternary ammonium) gemini surfactants in aqueous solution are significantly influenced by s, the number of methylene groups in the covalent spacer. However, the role played by s on the phase behavior of the single compounds has not been investigated in a similarly systematic way. Here, we report on the thermotropic phase behavior of the anhydrous compounds with s = 2-6, 8, 10, and 12, resorting to differential scanning calorimetry (DSC), polarized light microscopy (PLM), and X-ray diffraction (XRD). All of the compounds show a stepwise melting behavior, decomposing at 200 °C. As the spacer length increases, nonmonotonic trends are observed for the thermodynamic parameters of the thermotropic phase transitions, mesophase formation, and solid-state d spacings. In particular, the number and type of mesophases (ordered smectic phases and/or fluid smectic liquid crystals) depend critically on s. Further, upon heating molecules with s < 8 decompose before the liquid phase, while those with long spacers, s = 8-12, reach the isotropization (clearing) temperature, hence forming both ionic liquid crystals and ionic liquid phases. We demonstrate that the melting behavior and type of ionic mesophases formed by gemini molecules can be usefully manipulated by a simple structural parameter like the length of the covalent linker.

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Crystal structures of bis(quaternaryammonium bromide) surfactants, ethanediyl-1,2-bis(butyldimethylammonium bromide) dihydrate and propanediyl-1,3-bis(butyldimethylammonium bromide)

Cited by 10 publications

References 15 publications

Physicochemical Properties of New Dicationic Ether-Functionalized Low Melting Point Ammonium Salts

Physicochemical Properties of New Dicationic Ether-Functionalized Low Melting Point Ammonium Salts

Crystalline structures and mesomorphic properties of gemini diammonium surfactants with a pendant hydroxyl group

Critical Role of the Spacer Length of Gemini Surfactants on the Formation of Ionic Liquid Crystals and Thermotropic Behavior

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