Reaction of perfluoro-2-methylpent-2-ene and perfluoro-5-azanon-4-ene with aniline and its derivatives

Chi, Ki‐Whan; Fürin, G. G.; Bagryanskay, Irina Yu; Gatilov, Yuri V.

doi:10.1016/s0022-1139(00)00247-5

Cited by 14 publications

(3 citation statements)

References 8 publications

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“…Fluoroanilines constitute an important class of fluorinated compounds, since they show interesting biological activities and, consequently, are widely used as key intermediates in the manufacture of prominent pharmaceuticals and agrochemicals (pesticides, herbicides, and fungicides). − Fluoroaniline isomers are used in the synthesis of fluorobenzofuroxans . In general, benzofuroxan derivatives present remarkable biological activities, such as antimicrobial, fungicidal, algicidal, herbicidal, nematocidal, muscle relaxant, and vasorelaxant activity and anticancer effects .…”

Section: Introductionmentioning

confidence: 99%

Combined Experimental and Computational Study of the Thermochemistry of the Fluoroaniline Isomers

2007

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The standard (p degrees = 0.1 MPa) molar enthalpies of formation in the condensed phase of all the fluoroanilines, with the exception of the 2,3,5-trifluoroaniline compound, were derived from the standard molar energies of combustion in oxygen at T = 298.15 K, measured by rotating bomb combustion calorimetry. Calvet high-temperature vacuum sublimation experiments were performed to measure their enthalpies of vaporization or sublimation. These experiments allowed the determination of the standard molar enthalpies of formation in the gaseous phase and at T = 298.15 K. These values are also compared with estimates based on G3MP2B3 and BP86/6-31+G(d) computations, which have been extended also to the fluoroaniline that was not studied experimentally. The results are in close agreement with a mean deviation of approximately 3 kJ.mol-1. The largest difference between experimental and G3MP2B3 values is found for the pentafluoroaniline (-7.0 kJ.mol-1). For the three monofluoroanilines, the composite approach has been used also to compute gas-phase acidities, electron and proton affinities, ionization enthalpies and N-H bond dissociation enthalpies. The computed values compare well with available experimental results supporting the new computed data.

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Section: Introductionmentioning

confidence: 99%

Combined Experimental and Computational Study of the Thermochemistry of the Fluoroaniline Isomers

2007

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“…3,4 Fluoroanilines and their derivatives have revealed interesting biological activities, and consequently, are widely used as key intermediates in the manufacture of prominent pharmaceuticals and agrochemicals (pesticides, herbicides, and fungicides). [5][6][7] In view of the generally high chemical stability demonstrated by organofluorine compounds, they have achieved enormous industrial importance, especially in the synthesis of conducting polymers. [8][9][10] Previously, we have presented thermochemical studies of fluoro, 11 chloro, [12][13][14][15][16] bromo, 17 and iodoaniline 18 isomers.…”

Section: Introductionmentioning

confidence: 99%

Experimental and Computational Study of the Thermochemistry of the Fluoromethylaniline Isomers

2007

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The standard (po = 0.1 MPa) molar enthalpies of formation in the condensed phase of seven isomers of fluoromethylaniline were derived from the standard molar energies of combustion, in oxygen, to yield CO2(g), N2(g) and HF.10H2O(l), at T = 298.15 K, measured by rotating bomb combustion calorimetry. The standard molar enthalpies of vaporization or sublimation of these compounds, also at T = 298.15 K, were determined using Calvet microcalorimetry, while the enthalpies of fusion of the solid compounds were determined by differential scanning calorimetry. The standard molar enthalpies of formation in the gaseous phase, at T = 298.15 K, were derived from the former two experimental quantities. G3MP2//B3LYP calculations were performed for all possible fluoromethylanilines allowing the estimation of data for the isomers that were not studied experimentally. The Cox scheme was applied with two different approaches for the estimation of the standard molar enthalpies of formation of all the isomers studied, and this led to the conclusion that the literature values for the enthalpies of formation of the meta and para isomers of methylaniline seem to be not reliable. Further G3MP2//B3LYPs calculations on the methylaniline isomers yielded new values for the standard molar enthalpies of formation of the isomers of methylaniline, which have been tested under the Cox scheme, resulting in better estimates.

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“…Ki-Whan Chi et al [241] have reported an interesting result in the synthesis of novel heterocycles by using perfluoro-2-methyl-2-pentene 411 and various 1,3(S,N, N,N and N,C)binucleophilic reagents 412, as described in Scheme 133.…”

Section: Benzo Derivatives Of a Six-membered Ring With One Heteroatommentioning

confidence: 99%

Utilities of Some Carbon Nucleophiles in Heterocyclic Synthesis

Madkour¹,

Elgazwy

2007

COC

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New developments in the utilities of some carbon nucleophiles in heterocyclic synthesis are reviewed. General synthetic routes based on the utilization of carbon nucleophiles of active methylene are discussed. The major methods and modifications are analyzed. Heterocycles are ubiquitous in all kind of compounds of interest, and among all the possible synthetic methods of achieving their introduction into a structure, probably the use of a carbon nucleophile analogues are the most direct one. The present review deals with the generation and synthetic of carbon nucleophile, which uses as scaffold for the heterocyclic synthesis, and can be considered as an update review. Therefore the only references published upon the second quarter of 2003 are included, and the same restrictions to the literature coverage apply.

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Reaction of perfluoro-2-methylpent-2-ene and perfluoro-5-azanon-4-ene with aniline and its derivatives

Cited by 14 publications

References 8 publications

Combined Experimental and Computational Study of the Thermochemistry of the Fluoroaniline Isomers

Combined Experimental and Computational Study of the Thermochemistry of the Fluoroaniline Isomers

Experimental and Computational Study of the Thermochemistry of the Fluoromethylaniline Isomers

Utilities of Some Carbon Nucleophiles in Heterocyclic Synthesis

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