1987
DOI: 10.1039/c39870001159
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(3-Nitrenophenyl)methylene: a ground state quintet molecule having both carbenic and nitrenic atoms

Abstract: 3-Nitrenopheny1)methylene (I), a non-Kekule molecule with quintet ground state, has been generated photochemically from (3-azidopheny1)diazomethane in organic matrix at cryogenic temperatures.

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Cited by 26 publications
(12 citation statements)
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“…Thus, only quintet (3-nitrenophenyl)methylene was isolated in cryogenic matrices. 2 Here, we report on a quintet EPR spectrum formed in the photolysis of compound 1, which is consistent with expectations for a carbenonitrene system.…”
supporting
confidence: 89%
See 1 more Smart Citation
“…Thus, only quintet (3-nitrenophenyl)methylene was isolated in cryogenic matrices. 2 Here, we report on a quintet EPR spectrum formed in the photolysis of compound 1, which is consistent with expectations for a carbenonitrene system.…”
supporting
confidence: 89%
“…The D-value for 3 thus calculated falls between the relevant values for quintet m-phenylenedicarbenes (|D/hc| = 0.070-0.084 cm -1 ) 8(a), (b) and quintet m-phenylenedinitrene (|D/hc| = 0.156 cm -1 ), 8(a) and it is close to the D-value reported for (3-nitrenophenyl)methylene (|D/hc| = 0.124 cm -1 ). 2 The latter displayed a low-field signal at about 3200 G and the highest field transition at 7295 G.…”
mentioning
confidence: 94%
“…The first known organic spin quintet was formed by m -phenylene coupling of two methylenes . Later work showed that bisnitrene- m -phenylene systems also display a quintet ground state . More recent studies have focused on the relatively stable systems incorporating m -phenylene-coupled RNO fragment radicals .…”
Section: Introductionmentioning
confidence: 99%
“…Relatively few heterospin open-shell molecules have been made, by comparison to the numbers of systems having all the same spin carrying units. Mixed carbene/nitrene, carbene/nitroxide, nitrene/nitroxide, and nitroxide/radical-ion combinations have been synthesized and investigated. We aimed to synthesize systems incorporating phenoxyl and nitroxyl spin carrying units, both of which have been used in polyradicals and molecular magnetic materials.…”
Section: Introductionmentioning
confidence: 99%