ChemInform Abstract: N‐Aryl‐4‐dimethylaminopyridinium Salts and Their Arylating Properties.

Vizgert, R. V.; Sheiko, S. G.; Кулишова, Татьяна Петровна; Pekhtereva, T. M.; Nardekova, V. V.

doi:10.1002/chin.198723172

Cited by 2 publications

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“…[61][62][63] Only a few cases of conventional S N Ar reactions, where EWG groups activate the Xbound ipso-carbon toward the nucleophilic attack have been reported. These reactions include 2,4-dinitrobromobenzene, [64,65] 2,4-dinitroiodobenzene, [66] 2,4,6-trinitroiodobenzene, [67] tetrabromocatechol, [68][69][70] bromopyromellitic diimide, [71] and 2,3dibromonaphthalene-1,4,5,8-tetracarboxylic acid bisimide [72,73] as the arylation agents. All these reactions were conducted at high to moderate temperatures depending on the activating effect of substituents.…”

Section: N-arylation Of Azines By Arx (X = Br I)mentioning

confidence: 99%

Azine Steric Hindrances Switch Halogen Bonding to N‐Arylation upon Interplay with σ‐Hole Donating Haloarenenitriles

Baykov

Geyl

Ivanov

et al. 2021

Chemistry An Asian Journal

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An interplay between 4-bromo-and 4-iodo-5-nitrophthalonitriles (XNPN, X = Br or I) and any one of the azines (pyridine 1, 4-dimethylaminopyridine 2, isoquinoline 3, 4cyanopyridine 4, 2-methylpyridine 5, 2-aminopyridine 6, quinoline 7, 1-methylisoquinoline 8, and 2,2'-bipyridine 9) proceeds differently depending on steric and electronic effects of the heterocycles. Sterically unhindered azines 1-3 underwent N-arylation to give the corresponding azinium salts (characterized by 1 H and 13 C{H} NMR and high-resolution ESI-MS). In contrast, azines 4-9 with sterically hindered N atoms or bearing an electron-withdrawing substituent, form stable co-crystals with XNPN, where two interacting molecules are bound by halogen bonding. In all obtained cocrystals, X•••N structure-directed halogen bonds were recognized and theoretically evaluated including DFT calculations (PBE0-D3/def2-TZVP level of theory), QTAIM analysis, molecular electrostatic potential surfaces, and noncovalent interaction plot index. Estimated energies of halogen bonding vary from À 7.6 kcal/mol (for 6 • INPN) to À 11.4 kcal/mol (5 • INPN).

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Section: N-arylation Of Azines By Arx (X = Br I)mentioning

confidence: 99%

Azine Steric Hindrances Switch Halogen Bonding to N‐Arylation upon Interplay with σ‐Hole Donating Haloarenenitriles

Baykov

Geyl

Ivanov

et al. 2021

Chemistry An Asian Journal

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“…1 It is also used to prepare dinitrophenyl derivatives 2 of amino acids and related compounds. 3 In addition, it is an attractive reagent for the preparation of electron-deficient compounds.…”

Section: Introductionmentioning

confidence: 99%

Full multinuclear magnetic resonance analysis of 2,4‐dinitrofluorobenzene

Ariza‐Castolo

Guerrero‐Álvarez

Peralta-Cruz³

2002

Magnetic Reson in Chemistry

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The spin-lattice relaxation times of 13 C revealed their anisotropy components and it was evident that the dipole-dipole contribution of fluorine was an efficient mechanism for C-1 relaxation. The T 1 s of 1 H agreed with the classical description: at low temperature the main contribution is dipole-dipole relaxation and at high temperature the relaxation is dominated by the spin-rotation mechanism. A linear relationship between d 13 C .exp/ and s C using GIAO (hybrid functional B3LYP) was found. 3 J. 13 C, 1 H) and the 1 J.13 C, 13 C) have a relationship with the delocalization energies estimated by the NBO approach.

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ChemInform Abstract: N‐Aryl‐4‐dimethylaminopyridinium Salts and Their Arylating Properties.

Abstract: 172ChemInform Abstract The title compounds (III) are prepared for the first time. They are powerful arylating agents, as is shown by their reaction with piperidine (IV), which yields the N-aryl derivatives (V).

Cited by 2 publications

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Azine Steric Hindrances Switch Halogen Bonding to N‐Arylation upon Interplay with σ‐Hole Donating Haloarenenitriles

Azine Steric Hindrances Switch Halogen Bonding to N‐Arylation upon Interplay with σ‐Hole Donating Haloarenenitriles

Full multinuclear magnetic resonance analysis of 2,4‐dinitrofluorobenzene

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