Hyperconjugation in C6H7+ and Other Hydrocarbon Ions

Pickett, Lucy W.; Müller, Norbert; Mulliken, Robert S.

doi:10.1063/1.1699235

Cited by 21 publications

(15 citation statements)

References 6 publications

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“…of Mulliken et al for protonated benzene was very helpful (9). Our work in collaboration with Yonezawa, Nagata, and Kato provided a simple and pointed picture of theoretical interpretation of reactions (10), as well as the "overlap and orientation" principle proposed by Mulliken with regard to the orientation in molecular complexes (11).…”

Section: Interactionsmentioning

confidence: 77%

Role of Frontier Orbitals in Chemical Reactions

Fukui

1982

Science

2,254

817

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Section: Interactionsmentioning

confidence: 77%

Role of Frontier Orbitals in Chemical Reactions

Fukui

1982

Science

2,254

817

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“…Recent quantum-mechanical calculations suggest that benzenium ion itself, CeH? "1" (which is presumably of the complex type), should be stabilized to a considerable degree by hyperconjugation (238).…”

Section: B Polymethylbenzenes and Alkylbenzenes As Donorsmentioning

confidence: 99%

Aromatic Molecular Complexes of the Electron Donor-Acceptor Type.

Andrews¹

1954

Chem. Rev.

209

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“…In the ion two ~r-electrons are withdrawn to form a C-H bond on one of the aromatic carbon atoms ; thus a methylenic group results, which is assumed not to participate in the conjugation. The effect of hyperconjugation [2,7,8] will not be taken into account. The ion, then, is represented by a system of 2n-1 AO's and 2n-2 ~r-electrons.…”

Section: Introductionmentioning

confidence: 99%

The absorption spectra of aromatic carbonium ions in HF solution

1958

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The absorption spectra between 22003, and 10 000~ have been measured of the conjugate acids of a number of aromatic hydrocarbons dissolved in oxygen-free, anhydrous HF and HF-BFa mixtures, using a specially constructed cell. All spectra show very intense and characteristic absorption bands in the visible or near-ultra-violet region. In order to interpret these spectra, self-consistent field molecular orbital calculations have been made for the ground and excited states. The calculations, based on a ~r-electron model, were performed on an electronic digital computer.It could be shown in a number of cases that the aromatic hydrocarbon (in the absence of oxygen) is present in the acid solution as one type of protonated species. In these cases good agreement is found between the experimental and calculated spectra. Conversely, the theoretical predictions allowed of the interpretation of other cases where the aromatic hydrocarbon, when dissolved in the acid, forms a mixture of different ions, corresponding to a more complicated spectrum.Some of the solutions, if contacted with oxygen, display fundamental changes of spectrum. For perylene these are shown to be due to the rnonovalent positive ion of the hydrocarbon.

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Hyperconjugation in C6H7+ and Other Hydrocarbon Ions

Cited by 21 publications

References 6 publications

Role of Frontier Orbitals in Chemical Reactions

Role of Frontier Orbitals in Chemical Reactions

Aromatic Molecular Complexes of the Electron Donor-Acceptor Type.

The absorption spectra of aromatic carbonium ions in HF solution

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