Über einige Bis‐triarylmethyle. [Über Triarylmethyle. XV.]

Schlenk, W.; Brauns, Max

doi:10.1002/cber.19150480198

Cited by 46 publications

(10 citation statements)

References 4 publications

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“…Compounds (III) and (IV) were prepared starting from perdeuterodiphenyl [17] according to the syntheses described by Schlenk and Brauns [18]. The extent of deuteration was determined by mass spectrometry.…”

Section: (Rt)mentioning

confidence: 99%

ENDOR of biradicals

et al. 1969

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The ENDOR spectra of Tschitschibabin's hydrocarbon and certain of its specifically deuterated derivatives have been measured. To interpret these spectra the factors determining the ENDOR spectrum of a biradical are discussed in detail. The analysis reveals that the paramagnetic species present in solutions of Tschitschibabin's hydrocarbon and responsible for the solution electron resonance spectrum is a substituted p-biphenyldiphenylmethyl radical, thus resolving the biradical paradox. The substituent is thought to be the diphenylmethyl group in which case the radical could be formed through hydrogen abstraction by a thermally populated triplet.

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Section: (Rt)mentioning

confidence: 99%

ENDOR of biradicals

et al. 1969

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“…Similar experiments carried out previously with cyclopropyl-substituted TMM found that some of the product ring-opened, which was interpreted to mean that a singlet biradical was generated. Perhaps the oldest and most famous derivative of m -xylylene is Schlenk's hydrocarbon, 3 . This ground-state triplet biradical is well characterized. , A summary of the properties of other m -xylenes, including naptho and oxo derivatives, is provided elsewhere…”

mentioning

confidence: 99%

Photoelectron Spectroscopy of m-Xylylene Anion

1997

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The 351-nm photoelectron spectrum of the negative ion of 1,3-benzoquinodimethane (m-xylylene) is reported. Features are observed in the photoelectron spectrum corresponding to formation of the 3B2, 1A1, and 1B2 states of m-xylylene. The electron affinity of the triplet ground state is found to be 0.919 ± 0.008 eV, and vibrational frequencies of 290, 540, and 1500 cm-1 are obtained. The active modes are assigned to α-carbon bending, ring deformation, and methylene bending, respectively. The 1A1 state is found to lie 9.6 ± 0.2 kcal/mol higher in energy than the ground state, in good agreement with theoretical predictions. Vibrational frequencies of 265, 1000, and 1265 cm-1 are found for this state. The 1B2 is estimated to be <21.5 kcal/mol higher in energy than the ground state. Density functional calculations have been carried out on the negative ion, indicating that the 2B1 ion is a minimum on the potential energy surface, lying 2.9 kcal/mol lower in energy than the 2A2 ion, which is a transition state.

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“…Although the long‐term aspiration of designing commercially interesting organic magnetic materials remains elusive, fundamental studies have identified several families of organic species that are either ground state triplets or have low‐energy triplet states . These include carbenes, nitrenes, diradicals, nitrenium ions, certain aryl cations,, and antiaromatic cations such as cyclopentadiene . Recent computational and experimental studies in our laboratory have characterized several new types of ion‐diradicals that also have low energy triplet states.…”

Section: Introductionmentioning

confidence: 99%

The 3,5‐dinitroanilide anion: a singlet anilide anion with evidence for a thermally accessible triplet state

Perrotta

Falvey

2013

J of Physical Organic Chem

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Anilide anions derived from deprotonation of 4-nitroaniline and 3,5-dinitroaniline were examined by using DFT calculations, as well as ultraviolet and 1 H NMR experiments. The calculations indicate that the free anions are ground state singlets. However, when coordinated to a Li counterion, the 3,5-dinitroanilide anion is predicted to have a very narrow gap between the singlet and the triplet state. Spectroscopic data is consistent with this prediction. The UV-Vis spectrum of this anion shows a maximum absorbance at approximately 310 nm, which is in reasonable agreement with the spectrum for the singlet anion calculated by time-dependent density functional theory. On the other hand, NMR peak broadening and a modest Evans shift are consistent with the thermal population of a small amount of triplet anion.

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Über einige Bis‐triarylmethyle. [Über Triarylmethyle. XV.]

Cited by 46 publications

References 4 publications

ENDOR of biradicals

ENDOR of biradicals

Photoelectron Spectroscopy of m-Xylylene Anion

The 3,5‐dinitroanilide anion: a singlet anilide anion with evidence for a thermally accessible triplet state

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