Crystal structures of 1,4-di(1-imidazolyl)butane dihydrochloride, (C10H16N4)Cl2, and 1,4-di( 1-imidazolyl)butane dihydrate, C10H14N4 · 2H2O

Krolikowska, M.; Garbarczyk, J.

doi:10.1524/ncrs.2005.220.14.103

Cited by 4 publications

(5 citation statements)

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“…The two free water molecules are bonded together through hydrogen bond to form dimer. The imidazole rings in the title compound have trans-(ap) position in respect to C5-C5a bond (angle C4-C5-C5a-C4a, 180°), which shows that coordination of the imidazole ring nitrogen atoms causes no significant change in conformation of the title compound in comparison to the corresponding neutral molecule [23].…”

Section: Resultsmentioning

confidence: 93%

Synthesis and structure of photoluminescent di- and trinuclear copper(I) complexes assembled from alkane-bridged bis-imidazole

Jin

Wang

Sun

et al. 2009

Journal of Molecular Structure

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Section: Resultsmentioning

confidence: 93%

Synthesis and structure of photoluminescent di- and trinuclear copper(I) complexes assembled from alkane-bridged bis-imidazole

Jin

Wang

Sun

et al. 2009

Journal of Molecular Structure

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“…This situation is reminiscent of the dichotomies that exist between 4,4'-bis(imidazolyl)biphenyl and 1,1'-biphenyl-4,4'-diylbis(1H-benzimidazole), and between 1,4-di(1-imidazolyl)butane and 1,1'-butane-1,4-diylbis(1H-benzimidazole). 4,4'-Bis(imidazolyl)biphenyl 71,72 crystallizes as a monohydrate and 1,4-di(1-imidazolyl)butane 80 as a dihydrate, whereas 1,1'-biphenyl-4,4'-diylbis(1H-benzimidazole) 81,82 and 1,1'-butane-1,4diylbis(1H-benzimidazole) 83 both crystallize as anhydrous forms. It was thought originally that these dichotomies were the result of two joint contributions: first, the imine nitrogen of the imidazole ring is more basic than the imine nitrogen of the benzimidazole ring, 57 so the formation of a hydrate in which the water molecule is hydrogen-bonded to the heterocycle is expected to be favored for imidazole-based compounds.…”

Section: Structure Of 16-bis(1-benzimidazolyl)-24-hexadiyne (5)mentioning

confidence: 99%

Stability and solid-state polymerization reactivity of imidazolyl- and benzimidazolyl-substituted diacetylenes: pivotal role of lattice water

et al. 2013

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International audience1,6-Bis(1-imidazolyl)-2,4-hexadiyne (1) and1,6-bis(1-benzimidazolyl)-2,4-hexadiyne (5) have beenpreparedby a novel method that consists in refluxing excess imidazole and benzimidazole with 2,4-hexadiyne-1,6-diol bis(p-toluenesulfonate),pTS (3). This procedure is a viable alternative to the widely used Hay coupling protocol in case the target diyne possesses substituents capable of deactivating the copper catalyst by complexation. Diyne1crystallizes as a hydrate,1?H2O(2). For this compound, water is essential toachieve a crystalline material, and attempts to obtain crystals without included solvent were unsuccessful. In the structure of2, the organic fragments organize around the water molecule and interact with it through a dense network of hydrogen bonds. The CMC-CMC moieties are not oriented suitably for topochemical polymerization, and when trying to alter the organizationof the crystal by heating so as to induce polymerization, water is lost in an abrupt fashion that leads to instantaneous decomposition into polyaromatic-like species. Similar results were observed when water was removedin vacuo at room temperature. The benzimidazole-containing compound can be crystallized with water molecules (4)orwithout(5). X-ray crystallography shows that the structure of 5is organized by numerous C-H...N, C-H...p,andimidazolyl...imidazolyl p-p interactions. The diacetylene molecules almost have the right arrangement for topochemical polymerization, withpossibly reactingCMC-CMC fragments not beingparallel, a rare situation indiacetylene chemistry. Yet, experiments showthat topochemical polymerizationdoes not occur. Incorporationofwater in the lattice of5leads toa solvate that is topochemically reactive. Unlike2, however, water molecules in 4are not isolated but are organized as ribbons. Spectroscopic characterization of the polymer of4indicates that it is a blue phase polymer, with water coordinated to it. This study shows that it is possible to use water, and more generally solvent molecules, to transform a nonreactive diacetylene into a reactive one, even though this approach is less predictable than the cocrystal approach developed by Fowler, Lauher, and Goroff. The solvate approach is simple to implement, quite versatile because of the large rangeof solvents available, andonedoes not face theproblemof having to remove the host in case one needs to recover the polymer. Previous studies describing a similar approach are scarce

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“…For related literature, see: Dhal & Arnold (1992); Ding et al (2006); Fan et al (2006); Hoskins et al (1997); Krolikowska & Garbarczyk (2005); Ma et al (2000Ma et al ( , 2003; Moulton & Zaworotko (2001); Sato et al (1999); Yang et al (2006); .…”

Section: Related Literaturementioning

confidence: 99%

“…1). The protonation of imidazole groups have resulted in the changes of the bond parameters and configurations in comparison to known compounds (Krolikowska & Garbarczyk, 2005). The C-N bond lengths are in the range 1.325 3…”

Section: Data Collectionmentioning

confidence: 99%

1,1′-(Butane-1,4-diyl)bis(imidazolium) bis(perchlorate)

Yao

Zhang

et al. 2007

Acta Cryst E

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The asymmetric unit of the title compound, C10H16N42+·2ClO4−, consists of half of a centrosymmetric 1,1′‐(butane‐1,4‐diyl)bis(imidazolium) cation and one perchlorate anion. These ions are linked to each other by intermolecular bifurcated N—H...O hydrogen bonds to form infinite chains, which are further connected to each other by weak C—H...O hydrogen bonds to build up a three‐dimensional network.

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Crystal structures of 1,4-di(1-imidazolyl)butane dihydrochloride, (C10H16N4)Cl2, and 1,4-di( 1-imidazolyl)butane dihydrate, C10H14N4 · 2H2O

Cited by 4 publications

References 1 publication

Synthesis and structure of photoluminescent di- and trinuclear copper(I) complexes assembled from alkane-bridged bis-imidazole

Synthesis and structure of photoluminescent di- and trinuclear copper(I) complexes assembled from alkane-bridged bis-imidazole

Stability and solid-state polymerization reactivity of imidazolyl- and benzimidazolyl-substituted diacetylenes: pivotal role of lattice water

1,1′-(Butane-1,4-diyl)bis(imidazolium) bis(perchlorate)

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