The formation of dicyanoterphenyls by the interaction of terephthalonitrile dianion with biphenylcarbonitriles in liquid ammonia

Shteingarts, V. D.; Panteleeva, E. V.; Bagryanskaya, I. Yu.; Sal’nikov, Georgij E.

doi:10.3998/ark.5550190.0012.808

Cited by 2 publications

(1 citation statement)

References 5 publications

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“…The continuous R 2 2 (10) ring motif (see Fig. 1) (Bernstein et al, 1995), through CH� � �NC interactions, forms hydrogen-bonding networks of different dimensions (Dru ¨ck & Littke, 1978;Sakamoto et al, 2019;Li et al, 2007;van Rij & Britton, 1977), with unique one-dimensional hydrogenbonding pore structures (Ranganathan et al, 2007), planar layers (Wang & Zhao, 2008;Langhals et al, 2013;Jiao et al, 2018;He et al, 2004;Shteingarts et al, 2011) or undulating (wavy) laminar structures with trans connectivity (Lin et al, 2004;Zhu et al, 2022;Palde et al, 2008;Hua et al, 2016) (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of two iHOFs based on CH...NC hydrogen bonding

Qin,

Liu,

Luan

et al. 2024

Acta Crystallogr C Struct Chem

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Two ionic hydrogen-bonded organic frameworks (iHOFs) assembled from 4-cyano-N-(4-cyanobenzyl)pyridinium, have been crystallized with Br− and antimony(III) pentabromide, [SbBr5]2−, as counter-ions and characterized. These are 4-cyano-N-(4-cyanobenzyl)pyridinium bromide, C14H10N3 +·Br−, and bis[4-cyano-N-(4-cyanobenzyl)pyridinium] antimony(III) pentabromide, (C14H10N3)2[SbBr5]. The CH...NC interactions induced by templating anions construct disparate frameworks. Hirshfeld surface analysis indicated that these crystals exhibit two types of hydrogen-bonding interactions, specifically CH...NC and CH...Br. Consecutive reverse-parallel CH...NC hydrogen-bonding interactions in these crystals induced the formation of a large number of CH...NC bonds which exhibit both cis and trans configurations.

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Section: Introductionmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of two iHOFs based on CH...NC hydrogen bonding

Qin,

Liu,

Luan

et al. 2024

Acta Crystallogr C Struct Chem

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Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles

et al. 2018

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The first example of phenylation of fluorobenzonitriles with the sodium salt of a benzonitrile radical anion in liquid ammonia is presented. The reaction regioselectivity corresponds to the ortho- and para-fluorine atom substitution in fluorobenzonitrile with the phenyl moiety of the benzonitrile radical anion and affords 2- and 4-cyanobiphenyls in 40–90% yields. 3-Methoxybenzonitrile as well as 1-cyanonaphthalene radical anions were also successfully subjected to this interaction forming 3′-methoxycyanobiphenyls and (1-naphthyl)benzonitriles, respectively. The radical anion acts as an ipso-C-nucleophile with consequent loss of the cyano group. The revealed new type of radical anion reactivity opens up the prospect of developing a general approach to fluorinated cyanobisarenes on the basis of an interaction of the cyanoarene radical anion with fluorinated substrates activated to aromatic nucleophilic substitution.

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The formation of dicyanoterphenyls by the interaction of terephthalonitrile dianion with biphenylcarbonitriles in liquid ammonia

Cited by 2 publications

References 5 publications

Crystal structure and Hirshfeld surface analysis of two iHOFs based on CH...NC hydrogen bonding

Crystal structure and Hirshfeld surface analysis of two iHOFs based on CH...NC hydrogen bonding

Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles

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