Ammonium salts of carbamoyldicyanomethanide, C(CN)2(CONH2)−: Effects of hydrogen-bonding cations on anionic networks

Turner, David R.; MacDonald, R.; Lee, Wan Teng; Batten, Stuart Robert

doi:10.1039/b815926b

Cited by 17 publications

(6 citation statements)

References 26 publications

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“…Ag(cdm) was preapared according to previous reports. 31 Guanidine hydrochloride (0.336 g, 3.52 mmol) was dissolved in H 2 O/MeOH (50 ml, 1 : 1) and, whilst stirring, Ag(cdm) (1.140 g, 5.28 mmol) was added. The suspension was stirred in the dark for 4 h before the AgCl precipitate, and residual Ag(cdm), was removed by filtration.…”

Section: Experimental Synthesismentioning

confidence: 99%

Nitrile groups as hydrogen-bond acceptors in a donor-rich hydrogen-bonding network

2012

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Section: Experimental Synthesismentioning

confidence: 99%

Nitrile groups as hydrogen-bond acceptors in a donor-rich hydrogen-bonding network

2012

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“…To further investigate the effects of competetive donor species we examined alkylammonium salts of the cdm anion by synthesising compounds of the form (Me x H 4Àx N)(cdm), where x = 0-4. 129 The ammonium cations vary in their ability to compete for hydrogen bond acceptor sites depending on the number of NH hydrogen atoms that they possess. The differring degrees of methyl substitution also changes the degree to which the cations can direct hydrogen-bonding, with the NH 4 + cation able to hydrogen bond in a roughly spherical manner whereas others can only hydrogen bond from one 'face'.…”

Section: Hydrogen Bonding Networkmentioning

confidence: 99%

The chemistry and complexes of small cyano anions

et al. 2011

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The chemistry of the anions dicyanamide and tricyanomethanide (dca and tcm, respectively) has produced a plethora of discoveries over the past few decades, particularly in relation to transition-metal coordination polymers with magnetic coupling. Over recent years there have been an increasing number of reports of heterofunctionalised cyano-containing anions, typically derivatives of dicyanomethanide. Our own group has been particularly concerned with the amide- and nitroso-functionalised anions carbamoyldicyanomethanide (cdm) and dicyanonitrosomethanide (dcnm), respectively. This feature article examines the fascinating diversity of materials and complexes that can be obtained using small cyano anions, ranging from coordination polymers to heterometallic clusters and hydrogen bonding networks. In particular, we focus on results from our own laboratories in the past few years. The magnetic properties of these materials are briefly discussed.

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“…17 The cdm ligand has not been observed to undergo solvent addition as readily, with only one example of hydration observed, 24 although it has been shown to form strong hydrogen bonding motifs incorporating both the amide and nitrile functionalities. [18][19][20][21][22] Our current study is the first example of the addition of methanol to the cdm anion, resulting in the methyl 2-carbamoyl-2-cyanoethanimidate ligand (mcce) that is capable of chelating to a metal with a free bridging nitrile group 180 • opposed to the chelation site, Scheme 1. 2) is completed by bridging methoxides and oxide in addition to a terminal chloride ligand.…”

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“…Our recent work has focussed on the use of the small dinitrile anions dicyanonitrosomethanide (dcnm, [C(CN) 2 (NO)] -) and carbamoyldicyanomethanide (cdm, [C(CN) 2 (CONH 2 )] -). [16][17][18][19][20][21][22][23] The dcnm ligand has been observed to readily undergo nucleophilic addition of protic solvents, such as water and methanol and we have successfully incorporated the methanolated dcnm ligand, mcoe, into ferromagnetically coupled sheets of [Cu(mcoe) 2 ]. 17 The cdm ligand has not been observed to undergo solvent addition as readily, with only one example of hydration observed, 24 although it has been shown to form strong hydrogen bonding motifs incorporating both the amide and nitrile functionalities.…”

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confidence: 99%