Über die energetische Lage des niedrigsten Singulett‐und Triplettzustandes beim Schlenkschen und beim Müllerschen Kohlenwasserstoff

Schmidt, Reinhard H.; Brauer, H.‐D.

doi:10.1002/ange.19710831311

Cited by 18 publications

(1 citation statement)

References 11 publications

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“…3,4 The observed 3 changes in color can easily be explained by allowed and forbidden electronic transitions in monomeric radicals, which are present in the system in a considerable amount. For instance, the singlet quinoid structure of Chichibabin's hydrocarbon is characterized by a deep blue color in solution and by two intense absorption bands at 570and 310nm (c = 105 and 1.4-104 L tool cm -1, respecti,,ely) in the electronic spectnJm, t3 It was reasonable to assume that even more intense absorption bands in the electronic spectrum, shifted toward the tong-wavelength region, and a deeper color should correspond to the more developed singlet quinoid structure of molecule 1, if it exists.…”

Section: 'mentioning

confidence: 99%

Color centers in poly(arylenesulfophthalides) and the ground state of Müller's hydrocarbon molecule

Шишлов¹,

Asfandiarov²

2000

Russ Chem Bull

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Published data on the properties of Miiller's hydrocarbon are analyzed The total energies of several hydrocarbon biradicals with p-phenytene bridges, including Thiele "s, Chichibabin "s, and Mailer's hydrocarbons in the singtet and triplet states were caicu}ated by the AM I and PM3 scmiempiricat quantum-chemical methods. Contrar),. to popular opinion, our calculations revealed that the M/iller's hydrocarbon molecule has a triplet rather than singlet ground state. The results obtained make it possible to explain the limt that quinoid color centers do not l-arm in the course of reduction of poly(terphenylsulfophthatide). The calculated paramelcrs of eieclronic speclra for singiet states of some related biradicals are reported.

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Section: 'mentioning

confidence: 99%

Color centers in poly(arylenesulfophthalides) and the ground state of Müller's hydrocarbon molecule

Шишлов¹,

Asfandiarov²

2000

Russ Chem Bull

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Auf der Suche nach tieffarbigen organischen Verbindungen

Fabian

Zahradník

1989

Angewandte Chemie

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Stable Oxindolyl‐Based Analogues of Chichibabin's and Müller's Hydrocarbons

Wang

Phan

et al. 2017

Angewandte Chemie

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Chichibabinsa nd Müllersh ydrocarbons are classical open-shell singlet diradicaloids but they are highly reactive.H erein we report the successful synthesis of their respective stable analogues, OxR-2 and OxR-3,b ased on the newly developed oxindolyl radical. X-ray crystallographic analysis on OxR-2 reveals ap lanar quinoidal backbone similar to Chichibabinsh ydrocarbon, in accordance with its small diradical character (y 0 = 11.1 %) and large singlet-triplet gap (DE S-T = À10.8 kcal mol À1 ). Variable-temperature NMR studies on OxR-2 disclose as low cis/trans isomerization process in solution through ad iradical transition state,w ith am oderate energy barrier (DG°2 98K = 15-16 kcal mol À1 ). OxR-3 exhibits am uchl arger diradical character (y 0 = 80.6 %) and as maller singlet-triplet gap (DE S-T = À3.5 kcal mol À1 ), and thus can be easily populated to paramagnetic triplet diradical. Our studies provide an ew type of stable carbon-centered monoradical and diradicaloid.

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Über die energetische Lage des niedrigsten Singulett‐und Triplettzustandes beim Schlenkschen und beim Müllerschen Kohlenwasserstoff

Cited by 18 publications

References 11 publications

Color centers in poly(arylenesulfophthalides) and the ground state of Müller's hydrocarbon molecule

Color centers in poly(arylenesulfophthalides) and the ground state of Müller's hydrocarbon molecule

Auf der Suche nach tieffarbigen organischen Verbindungen

Stable Oxindolyl‐Based Analogues of Chichibabin's and Müller's Hydrocarbons

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