Formation and characterization of zwitterionic stereoisomers from the reaction of B(C6F5)3 and NEt2Ph: (E)- and (Z)-[EtPhN+=CHCH2-B- (C6F5)3]

Nicolas Millot; Catherine C. Santini; Bernard Fenet; Jean Marie Basset

doi:10.1002/1099-0682(200212)2002:12<3328::AID-EJIC3328>3.0.CO;2-P

Formation and characterization of zwitterionic stereoisomers from the reaction of B(C₆F₅)₃ and NEt₂Ph: (E)- and (Z)-[EtPhN⁺=CHCH₂-B^- (C₆F₅)₃]

Nicolas Millot, Catherine C. Santini^*, Bernard Fenet, Jean Marie Basset

^*Corresponding author for this work

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

100 Scopus citations

Abstract

The stoichiometric reaction of B(C₆F₅)₃ and NEt₂Ph I, at room temperature, in an aromatic solvent, has been investigated by 1D and 2D NMR spectroscopy (¹H, ¹¹B, ¹³C, ¹⁵N and ¹⁹F). No Et₂PhN·B(C₆F₅)₃ adduct was observed. An equilibrium between free B(C₆F₅)₃, NEt₂Ph, [HB(C₆F₅)₃]^-(HNEt₂Ph) ⁺ and two zwitterionic stereoisomers (E)- and (Z)-[EtPhN⁺=CH-CH₂-B^-(C₆ F₅)₃] (30%) in an E/Z ratio of 3:2 was observed. Whatever the protic reagent Z-OH [Z = H, SiPh₃, (c-C₅H₉)₇O₁₂Si₈, or silanol group of silica], all the equilibria involved in solutions of I are quantitatively displaced towards the ionic form [Z-O-B(C₆F₅)₃]^-(HNEt₂ Ph)⁺. In the case of dimethylaniline, besides free B(C₆F₅)₃ and Me₂NPh, the 1:1 adduct (C₆F₅)₃B·NMe₂Ph and an iminium salt [PhCH₃N= CH₂]⁺[HB(C₆F₅)₃] ^- have been identified.

Original language	English (US)
Pages (from-to)	3328-3335
Number of pages	8
Journal	European Journal of Inorganic Chemistry
Issue number	12
DOIs	https://doi.org/10.1002/1099-0682(200212)2002:12<3328::AID-EJIC3328>3.0.CO;2-P
State	Published - Dec 1 2002
Externally published	Yes

Keywords

Aniline
Boranes
NMR spectroscopy
Zwitterions

ASJC Scopus subject areas

Inorganic Chemistry

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10.1002/1099-0682(200212)2002:12<3328::AID-EJIC3328>3.0.CO;2-P

Cite this

@article{c2dcf203bb844aeca6313a2e4f6512de,

title = "Formation and characterization of zwitterionic stereoisomers from the reaction of B(C6F5)3 and NEt2Ph: (E)- and (Z)-[EtPhN+=CHCH2-B- (C6F5)3]",

abstract = "The stoichiometric reaction of B(C6F5)3 and NEt2Ph I, at room temperature, in an aromatic solvent, has been investigated by 1D and 2D NMR spectroscopy (1H, 11B, 13C, 15N and 19F). No Et2PhN·B(C6F5)3 adduct was observed. An equilibrium between free B(C6F5)3, NEt2Ph, [HB(C6F5)3]-(HNEt2Ph) + and two zwitterionic stereoisomers (E)- and (Z)-[EtPhN+=CH-CH2-B-(C6 F5)3] (30%) in an E/Z ratio of 3:2 was observed. Whatever the protic reagent Z-OH [Z = H, SiPh3, (c-C5H9)7O12Si8, or silanol group of silica], all the equilibria involved in solutions of I are quantitatively displaced towards the ionic form [Z-O-B(C6F5)3]-(HNEt2 Ph)+. In the case of dimethylaniline, besides free B(C6F5)3 and Me2NPh, the 1:1 adduct (C6F5)3B·NMe2Ph and an iminium salt [PhCH3N= CH2]+[HB(C6F5)3] - have been identified.",

keywords = "Aniline, Boranes, NMR spectroscopy, Zwitterions",

author = "Nicolas Millot and Santini, {Catherine C.} and Bernard Fenet and Basset, {Jean Marie}",

year = "2002",

month = dec,

day = "1",

doi = "10.1002/1099-0682(200212)2002:12<3328::AID-EJIC3328>3.0.CO;2-P",

language = "English (US)",

pages = "3328--3335",

journal = "European Journal of Inorganic Chemistry",

issn = "1434-1948",

publisher = "Wiley-VCH Verlag",

number = "12",

}

TY - JOUR

T1 - Formation and characterization of zwitterionic stereoisomers from the reaction of B(C6F5)3 and NEt2Ph

T2 - (E)- and (Z)-[EtPhN+=CHCH2-B- (C6F5)3]

AU - Millot, Nicolas

AU - Santini, Catherine C.

AU - Fenet, Bernard

AU - Basset, Jean Marie

PY - 2002/12/1

Y1 - 2002/12/1

N2 - The stoichiometric reaction of B(C6F5)3 and NEt2Ph I, at room temperature, in an aromatic solvent, has been investigated by 1D and 2D NMR spectroscopy (1H, 11B, 13C, 15N and 19F). No Et2PhN·B(C6F5)3 adduct was observed. An equilibrium between free B(C6F5)3, NEt2Ph, [HB(C6F5)3]-(HNEt2Ph) + and two zwitterionic stereoisomers (E)- and (Z)-[EtPhN+=CH-CH2-B-(C6 F5)3] (30%) in an E/Z ratio of 3:2 was observed. Whatever the protic reagent Z-OH [Z = H, SiPh3, (c-C5H9)7O12Si8, or silanol group of silica], all the equilibria involved in solutions of I are quantitatively displaced towards the ionic form [Z-O-B(C6F5)3]-(HNEt2 Ph)+. In the case of dimethylaniline, besides free B(C6F5)3 and Me2NPh, the 1:1 adduct (C6F5)3B·NMe2Ph and an iminium salt [PhCH3N= CH2]+[HB(C6F5)3] - have been identified.

AB - The stoichiometric reaction of B(C6F5)3 and NEt2Ph I, at room temperature, in an aromatic solvent, has been investigated by 1D and 2D NMR spectroscopy (1H, 11B, 13C, 15N and 19F). No Et2PhN·B(C6F5)3 adduct was observed. An equilibrium between free B(C6F5)3, NEt2Ph, [HB(C6F5)3]-(HNEt2Ph) + and two zwitterionic stereoisomers (E)- and (Z)-[EtPhN+=CH-CH2-B-(C6 F5)3] (30%) in an E/Z ratio of 3:2 was observed. Whatever the protic reagent Z-OH [Z = H, SiPh3, (c-C5H9)7O12Si8, or silanol group of silica], all the equilibria involved in solutions of I are quantitatively displaced towards the ionic form [Z-O-B(C6F5)3]-(HNEt2 Ph)+. In the case of dimethylaniline, besides free B(C6F5)3 and Me2NPh, the 1:1 adduct (C6F5)3B·NMe2Ph and an iminium salt [PhCH3N= CH2]+[HB(C6F5)3] - have been identified.

KW - Aniline

KW - Boranes

KW - NMR spectroscopy

KW - Zwitterions

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U2 - 10.1002/1099-0682(200212)2002:12<3328::AID-EJIC3328>3.0.CO;2-P

DO - 10.1002/1099-0682(200212)2002:12<3328::AID-EJIC3328>3.0.CO;2-P

M3 - Article

AN - SCOPUS:0036900744

SN - 1434-1948

SP - 3328

EP - 3335

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

IS - 12

ER -