1122-28-7Relevant articles and documents
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Ohtsuka
, p. 713 (1976)
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Shuman et al.
, p. 4532,4535 (1979)
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Harnessing chemical energy for the activation and joining of prebiotic building blocks
Liu, Ziwei,Wu, Long-Fei,Xu, Jianfeng,Bonfio, Claudia,Russell, David A.,Sutherland, John D.
, p. 1023 - 1028 (2020)
Life is an out-of-equilibrium system sustained by a continuous supply of energy. In extant biology, the generation of the primary energy currency, adenosine 5′-triphosphate and its use in the synthesis of biomolecules require enzymes. Before their emergence, alternative energy sources, perhaps assisted by simple catalysts, must have mediated the activation of carboxylates and phosphates for condensation reactions. Here, we show that the chemical energy inherent to isonitriles can be harnessed to activate nucleoside phosphates and carboxylic acids through catalysis by acid and 4,5-dicyanoimidazole under mild aqueous conditions. Simultaneous activation of carboxylates and phosphates provides multiple pathways for the generation of reactive intermediates, including mixed carboxylic acid–phosphoric acid anhydrides, for the synthesis of peptidyl–RNAs, peptides, RNA oligomers and primordial phospholipids. Our results indicate that unified prebiotic activation chemistry could have enabled the joining of building blocks in aqueous solution from a common pool and enabled the progression of a system towards higher complexity, foreshadowing today’s encapsulated peptide–nucleic acid system. [Figure not available: see fulltext.].
A tropylium annulated N-heterocyclic carbene
Appel, Sebastian,Brüggemann, Peter,Ganter, Christian
supporting information, p. 9020 - 9023 (2020/08/17)
Derivatives of the cationic tropylium annulated imidazolylidene ITrop+ are obtained by hydride abstraction from related cycloheptatriene compounds. Spectroscopic, structural and theoretical data indicate that, as a cationic relative of benzimidazolylidenes, ITrop+ has highly reduced σ-donor and strong π-acceptor character.
Push-pull molecules with a systematically extended π-conjugated system featuring 4,5-dicyanoimidazole
Kulhánek, Ji?í,Bure?, Filip,Pytela, Old?ich,Mikysek, Tomá?,Ludvík, Ji?í,R??i?ka, Ale?
scheme or table, p. 57 - 65 (2010/11/03)
Eighteen chromophores featuring 4,5-dicyanoimidazole as an acceptor moiety, a systematically enlarged π-conjugated spacer and methoxy and N,N-dimethylamino groups as donors were synthesised and characterised by X-ray analysis, electrochemistry, UV-Vis and fluorescence spectroscopy whilst NLO properties were calculated. Quantitative relationships between measured properties and structural features of the chromophores were also evaluated.