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Monoreduced 1,2‐dihydrocorannulene versus the parent corannulene
Author(s) -
Spisak Sarah N.,
Hoover Gabrielle C.,
Wei Zheng,
Zabula Alexander V.,
Filatov Alexander S.,
Petrukhina Marina A.
Publication year - 2015
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229615013145
Subject(s) - corannulene , ring (chemistry) , chemistry , potassium , salt (chemistry) , lithium (medication) , aromaticity , ion , crystallography , computational chemistry , molecule , organic chemistry , medicine , endocrinology
The monoanion of dihydrogenated corannulene isolated in the form of its potassium salt, namely tris(diglyme‐κ 3 O , O ′, O ′′)potassium hexacyclo[11.5.2.0 4,17 .0 7,16 .0 10,15 .0 14,18 ]icosa‐1,3,5,7(16),8,10(15),11,13,17‐nonaenide, [K(C 6 H 14 O 3 ) 3 ](C 20 H 12 ), has been structurally characterized for the first time. The X‐ray study confirms the previous NMR spectroscopic prediction that the two H atoms are attached to the same six‐membered ring to form 1,2‐dihydrocorannulene, thus destroying the aromaticity of only one arene ring of the corannulene core. The direct comparison of (C 20 H 12 ) − with the parent corannulene anion, (C 20 H 10 ) − , is provided to illustrate the geometry perturbations caused by rim hydrogenation.