Electron impact studies. CXIII. Aromatic nucleophilic substitution in the gas phase. The dinitrobenzenes. An ion cyclotron resonance study

1977 ◽  
Vol 30 (4) ◽  
pp. 795 ◽  
Author(s):  
JH Bowie ◽  
BJ Stapleton
Keyword(s):  
Nucleophilic Substitution ◽  
Gas Phase ◽  
Electron Impact ◽  
Cyclotron Resonance ◽  
Mass Spectra ◽  
Major Ions ◽  
Abundance Ratio ◽  
Negative Ion ◽  
Ion Cyclotron Resonance ◽  
Aromatic Nucleophilic Substitution

The negative ion mass spectra derived from the three dinitrobenzenes show NO2-, [M-?-NO?]- and M-? as major ions. The i.c.r. spectrum of o- dinitrobenzene shows the formation of the adducts [M+NO2-]-, [M+(M-?-NO?)- ]- and 2M-?, but the m- and p-dinitrobenzenes only produce the adduct [M+NO2-]-. The nucleophile Cl- adds to each of the three dinitrobenzene neutrals in the abundance ratio o >> m ≈ p. Evidence is presented which suggests that the neutral products formed by the reaction between NO2- and o-dinitrobenzene are dinitro- and trinitro-benzenes, whereas those resulting from the interaction of Cl- with o-dinitrobenzene are chloronitrobenzene and a chloro-dinitrobenzene.

Electron impact studies. XCIII. The reactions of negative ions from 3- and 4-nitrophthalic anhydrides

1975 ◽  
Vol 28 (3) ◽  
pp. 563 ◽  
Author(s):  
JH Bowie ◽  
BD Williams
Keyword(s):  
Electron Impact ◽  
Phthalic Anhydride ◽  
Cyclotron Resonance ◽  
Mass Spectra ◽  
Negative Ions ◽  
Negative Ion ◽  
Ion Cyclotron Resonance ◽  
Impact Studies ◽  
Ion Molecule Reactions ◽  
Positive Ions

Possible structures for some rearrangement ions in the negative ion mass spectra of 3- and 4-nitro- phthalic anhydride are suggested from an examination of the + E spectra obtained by the conversion of the negative ions to positive ions by charge-stripping reactions. The reactivities of the non-decomposing negative ions have been investigated by observation of their ion-molecule reactions with the neutral anhydride in the cell of an ion cyclotron resonance spectrometer.

Electron impact studies. CXVIII. An ion cyclotron resonance study of the reactivity of negative ions derived from ethenetetracarbonitrile. Anionic polymerization in the gas phase

1977 ◽  
Vol 30 (10) ◽  
pp. 2161 ◽  
Author(s):  
JH Bowie
Keyword(s):  
Gas Phase ◽  
Electron Impact ◽  
Anionic Polymerization ◽  
Cyclotron Resonance ◽  
Negative Ions ◽  
Ion Cyclotron Resonance ◽  
Impact Studies ◽  
Stable Adduct ◽  
Ion Cyclotron

.The [M·–l CN·I- species from ethenetetracarbonitrile (tetracyanoethylene) reacts with neutral ethene- tetracarbonitrile to give the stable adduct C11N7-. The decomposing form of this adduct eliminates C2N2 to produce C,9N5- which may react with ethenetetracarbonitrile to yield C15N,9-. Analogous anionic polymerization reactions yield a number of detectable peaks in the i.c.r. spectrum of tetra- cyanoethylene, with the structures of the ions possibly corresponding to a. Diagram Polymerization of this type can also be initiated by other nucleophiles including Cl-, Br-, I- and CF3CO2-.

Electron impact studies. LXXXVIII. formation of an adduct between the trifluoroacetate anion and perfluoroacetic anhydride by ion cyclotron resonance

1974 ◽  
Vol 27 (9) ◽  
pp. 1923 ◽  
Author(s):  
JH Bowie ◽  
BD Williams
Keyword(s):  
Gas Phase ◽  
Electron Impact ◽  
Direct Observation ◽  
Cyclotron Resonance ◽  
Ion Cyclotron Resonance ◽  
Phase Reaction ◽  
Gas Phase Reaction ◽  
Tetrahedral Intermediate ◽  
Impact Studies ◽  
Association Complex

The gas phase reaction between the trifluoroacetate anion and perfluoroacetic anhydride produces a 1 : 1 adduct. The decompositions of this adduct suggest a tetrahedral species rather than a loose association complex. If this is so, this constitutes the first direct observation of the formation of a tetrahedral intermediate produced by anionic displacement at a carbonyl centre.

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