Gas-phase anionic oligomerization of methyl acrylate initiated by F3C-, NCCH2-, and allyl anions

McDonald, Richard N.; Chowdhury, A. Kasem

doi:10.1021/ja00346a016

Cited by 19 publications

(31 citation statements)

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“…Rate constants for the displacement of C1-and Br-from CH3Cl and CH3Br respectively have been measured for several nucleophiles in order to provide a basis for comparison. Furthermore these measurements have verified whether the rate constants for SN2 substitutions previously measured with either the Ion Cyclotron Resonance (ICR) or the Flowing Afterglow (FA) method could be reproduced with our FT-ICR instrument (21, 23,24). The data have been collected in Tables 3 and 4.…”

Section: Ch3sch3supporting

confidence: 64%

Gas phase chemistry of α-thio carbanions

Ingemann¹,

Nibbering²

1984

Can. J. Chem.

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STEEN INGEMANN and NICO M. M. NIBBERING. Can. J. Chem. 62, 2273 (1984. Proton abstraction from CH3SCH3 and C6H5SCH3 in the gas phase has been studied by the use of Fourier Transform Ion Cyclotron Resonance (FI-ICR) mass spectrometry. The gas phase acidity of CH3SCH3 is reported to be AG;~, = 1615 r 8 kJ/mol. The methyl group in C6H5SCH3 is observed to be the most acidic position. The gas phase acidity of this group is determined to be AG;~, = 1560 +. [Traduit par le journal]

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Section: Ch3sch3supporting

confidence: 64%

Gas phase chemistry of α-thio carbanions

Ingemann¹,

Nibbering²

1984

Can. J. Chem.

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“…5,35 In their study, the (AN) 3 -ion is produced more efficiently than (AN) -. 5 Thus, it is expected that (AN) 3 can accept the excess electron more efficiently than the AN molecule. Present calculations reveal that the electron of the Na atom is partly transferred to AN in Na(AN), despite the poor ability of AN to accept the excess electron.…”

Section: Resultsmentioning

confidence: 99%

“…2,3 In their study, the ionmolecule reaction between CH 2 CN -ion and AN was used for the initial step of the oligomerization. 2 The oligomer, NCCH 2 s (AN) n sAN -, is produced up to n ) 3 in this reaction.…”

Section: Introductionmentioning

confidence: 99%

Anionic Oligomerization of Acrylonitrile Molecules Initiated by Intracluster Electron Transfer from Alkali Metal Atoms: Photoionization Mass Spectrometry of M(CH₂CHCN)_n (M = Li, Na, and K)

1999

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We investigated the photoionization mass spectrometry of clusters of alkali metal atoms (M ) Li, Na and K) solvated with acrylonitrile (AN; CH 2 dCHCN) molecules to obtain the information on size-dependent stability of the clusters. In the photoionization mass spectra of M m (AN) n , strong ion signals were observed at M + -(AN) 3 . The M + (AN) n (n ) 6 and 9) ions were also clearly observed as magic numbers in the mass spectra of M ) Na and K. By comparison with the mass spectrum of cluster ions formed by ion-molecule reactions in the cluster source, these magic numbers were found to be due to the stability of neutral clusters. These results are explained by the intracluster electron transfer from an alkali metal atom to AN molecules followed by anionic oligomerization. The results of the calculation for Na(AN) based on density functional theory also supports this consideration.

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“…In recent years, ionic oligomerization in the gas phase has also been studied to some extent in order to elucidate the elementary reaction processes [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. For this purpose, gas phase studies should have some advantages from the following features; (1) it is possible to discuss reactivity which is free from the solvent effect, and (2) assignment of the sequentially polymerized products are directly obtained by the mass spectrometric method.…”

Section: Introductionmentioning

confidence: 99%

“…For this purpose, gas phase studies should have some advantages from the following features; (1) it is possible to discuss reactivity which is free from the solvent effect, and (2) assignment of the sequentially polymerized products are directly obtained by the mass spectrometric method. As one of the gas phase studies, a flowing ionmolecule reaction was investigated to elucidate the reaction mechanism of anionic oligomerization [1,2]. In these studies, negative ions such as F 3 C − , NCCH − 2 and C 3 H − 5 were applied as the reaction initiator in the gas phase flowing afterglow apparatus.…”

Section: Introductionmentioning

confidence: 99%

Intracluster electron transfer from a metal atom/cluster followed by anionic oligomerization of vinyl molecules

Ohshimo

Tsunoyama

Misaizu

et al. 2001

The European Physical Journal D

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Intracluster electron transfer and oligomerization reaction were investigated by mass spectrometry of clusters of alkali metal atom (M) with acrylonitrile (AN; CH2=CHCN). In the photoionization mass spectra of M(AN)n, magic numbers were clearly observed at n = 3k (k = 1-4 for M = Na and K, k = 1 for M = Li). The results of photodissociation of neutral K(AN)n indicate that the n = 3 cluster has an anomalous stability relative to other sizes of clusters. The C=C bond in vinyl molecules is also found to be necessary to form the magic numbers by measuring the photoionization mass spectrum of K atom with propionitrile. These results strongly support the intracluster anionic oligomerization reaction initiated by electron transfer from the alkali atom. The quantum chemical calculations have revealed that the evaporation induced by excess energy generated by intracluster oligomerization is important to form the magic numbers in the present clusters.

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Gas-phase anionic oligomerization of methyl acrylate initiated by F3C-, NCCH2-, and allyl anions

Cited by 19 publications

References 0 publications

Gas phase chemistry of α-thio carbanions

Gas phase chemistry of α-thio carbanions

Anionic Oligomerization of Acrylonitrile Molecules Initiated by Intracluster Electron Transfer from Alkali Metal Atoms: Photoionization Mass Spectrometry of M(CH₂CHCN)_n (M = Li, Na, and K)

Intracluster electron transfer from a metal atom/cluster followed by anionic oligomerization of vinyl molecules

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Gas-phase anionic oligomerization of methyl acrylate initiated by F3C-, NCCH2-, and allyl anions

Cited by 19 publications

References 0 publications

Gas phase chemistry of α-thio carbanions

Gas phase chemistry of α-thio carbanions

Anionic Oligomerization of Acrylonitrile Molecules Initiated by Intracluster Electron Transfer from Alkali Metal Atoms: Photoionization Mass Spectrometry of M(CH2CHCN)n (M = Li, Na, and K)

Intracluster electron transfer from a metal atom/cluster followed by anionic oligomerization of vinyl molecules

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Anionic Oligomerization of Acrylonitrile Molecules Initiated by Intracluster Electron Transfer from Alkali Metal Atoms: Photoionization Mass Spectrometry of M(CH₂CHCN)_n (M = Li, Na, and K)