Fluorinated Amines

Henne, Albert L.; Stewart, Jay J.

doi:10.1021/ja01612a057

Cited by 38 publications

(27 citation statements)

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“…The strong electronegative inductive effect of fluorine in carbon chains decreases the basicity of fluorinated amines (Table 21) (209], and increases considerably the acidity of fluorinated alcohols, phenols, and acids. Perfluorinated alcohols exhibit the acidity of phenols (Table 22) [210][211][212], pentafluorophenol (Ka=4.79 X 10-6 ) [213] the acidity of organic acids, and perfluorinated carboxylic acids the acidity of mineral acids (Table 23) [214].…”

Section: Physicochemical Propertiesmentioning

confidence: 99%

Organic Fluorine Chemistry

Hudlický

1971

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Section: Physicochemical Propertiesmentioning

confidence: 99%

Organic Fluorine Chemistry

Hudlický

1971

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“…For a diamine in which the two secondary amines have a CH 2 (CF 2 ) 3 and a CH 2 (CF 2 )CF 3 substituent, the pK a was reported to be too low to be measurable by titration in aqueous solution. 20 The two methylene groups separating the trifluoromethyl group from the amino group in 3,3,3-trifluoropropylamine already affect the pK a much less (pK a 8.7), 19 and ab initio calculations of proton affinities of primary amines with tri-, tetra-, and pentamethylene spacers imply that the trimethylene spacer is quite efficient at reducing the electron withdrawing effect of a perfluoroalkyl substituent. 18 Relative basicities in CDCl 3 are known for trialkylamines with the general structure N[(CH 2 ) n Rf m ], where Rf m represents a perfluoroalkyl substituent and n takes a value between 3 and 5.…”

Section: Introductionmentioning

confidence: 99%

Coordinative Properties of Highly Fluorinated Solvents with Amino and Ether Groups

et al. 2005

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In spite of the widespread use of perfluorinated solvents with amino and ether groups in a variety of application fields, the coordinative properties of these compounds are poorly known. It is generally assumed that the electron withdrawing perfluorinated moieties render these functional groups rather inert, but little is known quantitatively about the extent of their inertness. This paper reports on the interactions between inorganic monocations and perfluorotripentylamine and 2H-perfluoro-5,8,11-trimethyl-3,6,9,12-tetraoxapentadecane, as determined with fluorous liquid-membrane cationselective electrodes doped with tetrakis[3,5-bis(perfluorohexyl)phenyl]borate salts. The amine does not undergo measurable association with any ion tested, and its formal pK a is shown to be smaller than -0.5. This is consistent with the nearly planar structure of the amine at its nitrogen center, as obtained with density functional theory calculations. The tetraether interacts very weakly with Na + and Li + . Assuming 1:1 stoichiometry, formal association constants were determined to be 2.3 and 1.5 M -1 , respectively. This disproves an earlier proposition that the Lewis base character in such compounds may be non-existent. Due to the extremely low polarity of fluorous solvents and the resulting high extent of ion pair formation, a fluorophilic electrolyte salt with perfluoroalkyl substituents on both the cation and the anion had to be developed for these experiments. In its pure form, this first fluorophilic electrolyte salt is an ionic liquid with a glass transition temperature, T g , of -18.5 °C. Interestingly, the molar conductivity of solutions of this salt increases very steeply in the high concentration range, making it a particularly effective electrolyte salt.

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“…HBr [21] or three stage synthesis from 1-chloro-3,3,3-trifluoropropene [22], see also references therein). Acid 6 was transformed into chloroanhydride 7 by the treatment with PCl 5 according to [23] that is a modified method reported in [24]. Previously, 3,3,3-trifluoroisocyanate 8 was synthesized from 3,3,3-trifluoroethylamine and phosgene [25–27], by thermal degradation of N -diphenyl- N '-(3,3,3-trifluoroethyl) urea [28, 29].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 3,3,3-trifluoroethyl isocyanate, carbamate and ureas. Anticancer activity evaluation of N-(3,3,3-trifluoroethyl)-N′-substituted ureas

Luzina

Popov

2015

Journal of Fluorine Chemistry

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A new method is described for producing 3,3,3-trifluoroethyl isocyanate from perfluoroisobutene (PFIB). Isocyanate was used for synthesis of carbamates and ureas. A series of trifluoroethyl-substituted ureas has been tested in the National Cancer Institute (NCI, Bethesda, USA) by the NCI-60 DTP Human Tumor Cell Line Screening Program at a single high dose (10−5 M). The moderate anticancer activity was shown against some types of cancer on the individual human cell lines for leukemia, non-small cell lung cancer and renal cancer.

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Fluorinated Amines

Cited by 38 publications

References 0 publications

Organic Fluorine Chemistry

Organic Fluorine Chemistry

Coordinative Properties of Highly Fluorinated Solvents with Amino and Ether Groups

Synthesis of 3,3,3-trifluoroethyl isocyanate, carbamate and ureas. Anticancer activity evaluation of N-(3,3,3-trifluoroethyl)-N′-substituted ureas

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