Reactions of the perfluoroalkyltriazapentadiene Ph2N3C2(C3F7) 2H with acids, bases, and water

A. R. Siedle; Robert J. Webb; Myles Brostrom; Shih Hung Chou; David A. Weil; Richard A. Newmark; Fred E. Behr; Victor G. Young

doi:10.1021/ic020716q

Reactions of the perfluoroalkyltriazapentadiene Ph₂N₃C₂(C₃F₇) ₂H with acids, bases, and water

A. R. Siedle, Robert J. Webb, Myles Brostrom, Shih Hung Chou, David A. Weil, Richard A. Newmark, Fred E. Behr, Victor G. Young

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

Treatment of the bis(perfluoroalkyl)triazapentadiene PhN=C(C₃F₇)-N=C(C₃F₇)-NHPh, 2, with bases affords salts of the conjugate base. Alkylation of the Na⁺ salt with CH₃l yields PhN=C(C₃F₇)-N=C(C₃F₇)-NMePh. The crystal structure of [Bu₄N][Ph₂N₃C₂ (C₃F₇)₂] demonstrates a twisted, zigzag geometry for the anion in the solid state, but in solution, it is conformationally unstable. Both compounds are stable in aqueous methanol, but hydrolysis occurs under acidic conditions. Protonation with CF₃SO₃H acid occurs at the sp² nitrogen to give [PhN_H^..HC(C₃F₇) ^..N^..-C-(C₃F₇)- ^..NHPh][CF₃SO₃]. Heating 2 in CF₃SO₃H produces 2,4-bis(heptafluoropropyl)-1,3-quinazoline.

Original language	English (US)
Pages (from-to)	2596-2601
Number of pages	6
Journal	Inorganic chemistry
Volume	42
Issue number	8
DOIs	https://doi.org/10.1021/ic020716q
State	Published - Apr 21 2003

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title = "Reactions of the perfluoroalkyltriazapentadiene Ph2N3C2(C3F7) 2H with acids, bases, and water",

abstract = "Treatment of the bis(perfluoroalkyl)triazapentadiene PhN=C(C3F7)-N=C(C3F7)-NHPh, 2, with bases affords salts of the conjugate base. Alkylation of the Na+ salt with CH3l yields PhN=C(C3F7)-N=C(C3F7)-NMePh. The crystal structure of [Bu4N][Ph2N3C2 (C3F7)2] demonstrates a twisted, zigzag geometry for the anion in the solid state, but in solution, it is conformationally unstable. Both compounds are stable in aqueous methanol, but hydrolysis occurs under acidic conditions. Protonation with CF3SO3H acid occurs at the sp2 nitrogen to give [PhNH..HC(C3F7) ..N..-C-(C3F7)- ..NHPh][CF3SO3]. Heating 2 in CF3SO3H produces 2,4-bis(heptafluoropropyl)-1,3-quinazoline.",

author = "Siedle, {A. R.} and Webb, {Robert J.} and Myles Brostrom and Chou, {Shih Hung} and Weil, {David A.} and Newmark, {Richard A.} and Behr, {Fred E.} and Young, {Victor G.}",

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T1 - Reactions of the perfluoroalkyltriazapentadiene Ph2N3C2(C3F7) 2H with acids, bases, and water

AU - Siedle, A. R.

AU - Webb, Robert J.

AU - Brostrom, Myles

AU - Chou, Shih Hung

AU - Weil, David A.

AU - Newmark, Richard A.

AU - Behr, Fred E.

AU - Young, Victor G.

PY - 2003/4/21

Y1 - 2003/4/21

N2 - Treatment of the bis(perfluoroalkyl)triazapentadiene PhN=C(C3F7)-N=C(C3F7)-NHPh, 2, with bases affords salts of the conjugate base. Alkylation of the Na+ salt with CH3l yields PhN=C(C3F7)-N=C(C3F7)-NMePh. The crystal structure of [Bu4N][Ph2N3C2 (C3F7)2] demonstrates a twisted, zigzag geometry for the anion in the solid state, but in solution, it is conformationally unstable. Both compounds are stable in aqueous methanol, but hydrolysis occurs under acidic conditions. Protonation with CF3SO3H acid occurs at the sp2 nitrogen to give [PhNH..HC(C3F7) ..N..-C-(C3F7)- ..NHPh][CF3SO3]. Heating 2 in CF3SO3H produces 2,4-bis(heptafluoropropyl)-1,3-quinazoline.

AB - Treatment of the bis(perfluoroalkyl)triazapentadiene PhN=C(C3F7)-N=C(C3F7)-NHPh, 2, with bases affords salts of the conjugate base. Alkylation of the Na+ salt with CH3l yields PhN=C(C3F7)-N=C(C3F7)-NMePh. The crystal structure of [Bu4N][Ph2N3C2 (C3F7)2] demonstrates a twisted, zigzag geometry for the anion in the solid state, but in solution, it is conformationally unstable. Both compounds are stable in aqueous methanol, but hydrolysis occurs under acidic conditions. Protonation with CF3SO3H acid occurs at the sp2 nitrogen to give [PhNH..HC(C3F7) ..N..-C-(C3F7)- ..NHPh][CF3SO3]. Heating 2 in CF3SO3H produces 2,4-bis(heptafluoropropyl)-1,3-quinazoline.

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Reactions of the perfluoroalkyltriazapentadiene Ph₂N₃C₂(C₃F₇) ₂H with acids, bases, and water

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