Electronic stricture and reactivity of phenyl and pentafluorophenylsubstituted N,N-dichloroamides and -amines

Abstract

The charge distribution in the polyfluoroaromatic N,N-dichloroamides and -amines and their hydrocarbon analogues has been established from the X-ray fluorescent ClK_α^- and SK_α-spectra and X-ray photoelectron spectra of chlorine, sulphur and nitrogen in comparoson with data obtained from NQR ³⁵Cl frequencies and semiempirical calculations by CNDO/2. The action of sulphur and selenium on the N,N-dichloroamides of pentafluorobenzenesulphonic acid and pentafluorobenzoic acid leads to the corresponding S,S-dichlorosulphimines and Se,Se-dichloroselenoimines respectively. The polyfluoroaromatic N,N-dichloroamimes have been found to form polyfluorinated trans-azobenzenes under the same conditions. The mechanism of these reactions has been discussed.

Original language	English
Pages (from-to)	1-14
Number of pages	14
Journal	Journal of Fluorine Chemistry
Volume	17
Issue number	1
DOIs	https://doi.org/10.1016/S0022-1139(00)85246-X
Publication status	Published - 1981

ASJC Scopus subject areas

Inorganic Chemistry
Organic Chemistry
Materials Chemistry
Polymers and Plastics

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10.1016/S0022-1139(00)85246-X

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@article{0d2852d85a3d4b1dbaca4150b4a8dec5,

title = "Electronic stricture and reactivity of phenyl and pentafluorophenylsubstituted N,N-dichloroamides and -amines",

abstract = "The charge distribution in the polyfluoroaromatic N,N-dichloroamides and -amines and their hydrocarbon analogues has been established from the X-ray fluorescent ClKα- and SKα-spectra and X-ray photoelectron spectra of chlorine, sulphur and nitrogen in comparoson with data obtained from NQR 35Cl frequencies and semiempirical calculations by CNDO/2. The action of sulphur and selenium on the N,N-dichloroamides of pentafluorobenzenesulphonic acid and pentafluorobenzoic acid leads to the corresponding S,S-dichlorosulphimines and Se,Se-dichloroselenoimines respectively. The polyfluoroaromatic N,N-dichloroamimes have been found to form polyfluorinated trans-azobenzenes under the same conditions. The mechanism of these reactions has been discussed.",

author = "Dolenko, {G. N.} and Zibarev, {A. V.} and Krupoder, {S. A.} and Mazalov, {L. N.} and Poleshchuk, {O. Ch} and Furin, {G. G.} and Khudorozhko, {G. F.} and Yakobson, {G. G.}",

year = "1981",

doi = "10.1016/S0022-1139(00)85246-X",

language = "English",

volume = "17",

pages = "1--14",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier BV",

number = "1",

}

TY - JOUR

T1 - Electronic stricture and reactivity of phenyl and pentafluorophenylsubstituted N,N-dichloroamides and -amines

AU - Dolenko, G. N.

AU - Zibarev, A. V.

AU - Krupoder, S. A.

AU - Mazalov, L. N.

AU - Poleshchuk, O. Ch

AU - Furin, G. G.

AU - Khudorozhko, G. F.

AU - Yakobson, G. G.

PY - 1981

Y1 - 1981

N2 - The charge distribution in the polyfluoroaromatic N,N-dichloroamides and -amines and their hydrocarbon analogues has been established from the X-ray fluorescent ClKα- and SKα-spectra and X-ray photoelectron spectra of chlorine, sulphur and nitrogen in comparoson with data obtained from NQR 35Cl frequencies and semiempirical calculations by CNDO/2. The action of sulphur and selenium on the N,N-dichloroamides of pentafluorobenzenesulphonic acid and pentafluorobenzoic acid leads to the corresponding S,S-dichlorosulphimines and Se,Se-dichloroselenoimines respectively. The polyfluoroaromatic N,N-dichloroamimes have been found to form polyfluorinated trans-azobenzenes under the same conditions. The mechanism of these reactions has been discussed.

AB - The charge distribution in the polyfluoroaromatic N,N-dichloroamides and -amines and their hydrocarbon analogues has been established from the X-ray fluorescent ClKα- and SKα-spectra and X-ray photoelectron spectra of chlorine, sulphur and nitrogen in comparoson with data obtained from NQR 35Cl frequencies and semiempirical calculations by CNDO/2. The action of sulphur and selenium on the N,N-dichloroamides of pentafluorobenzenesulphonic acid and pentafluorobenzoic acid leads to the corresponding S,S-dichlorosulphimines and Se,Se-dichloroselenoimines respectively. The polyfluoroaromatic N,N-dichloroamimes have been found to form polyfluorinated trans-azobenzenes under the same conditions. The mechanism of these reactions has been discussed.

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