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  Verdazyls. Part 33. EPR and ENDOR studies of 6-oxo- and 6-thioxoverdazyls. X-Ray molecular structure of 1,3,5-triphenyl-6-oxoverdazyl and 3-tert-butyl-1,5-diphenyl-6-thioxoverdazyl

Neugebauer, F. A., Fischer, H., & Krieger, C. (1993). Verdazyls. Part 33. EPR and ENDOR studies of 6-oxo- and 6-thioxoverdazyls. X-Ray molecular structure of 1,3,5-triphenyl-6-oxoverdazyl and 3-tert-butyl-1,5-diphenyl-6-thioxoverdazyl. Journal of the Chemical Society-Perkin Transactions 2, 1993(3), 535-544. doi:10.1039/P29930000535.

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 Creators:
Neugebauer, Franz A.1, Author           
Fischer, Hans1, Author           
Krieger, Claus1, Author           
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1Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society, ou_1497706              

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 Abstract: A range of 6-oxoverdazyls 2b–h and 6-thioxoverdazyls 3a–c and 3e–h has been directly prepared by dehydrogenation of the corresponding 1, 4, 5, 6-tetrahydro-1, 2, 4, 5-tetrazin-3(2H)-ones 5b–h and thiones 7a–c and 7e–hwith lead dioxide, potassium hexacyanoferrate (III), or bis(4-methylphenyl)-aminyl. X-Ray analyses reveal a nearly planar verdazyl framework for the oxoverdazyl 2a, whereas the thioxoverdazyl 3ftakes on a flat boat conformation. In the latter, owing to the bulky sulfur the N-phenyl groups are considerably twisted out of the plane of the verdazyl ring. Electronic absorption spectra of the deeply coloured radicals exhibit characteristic bands in the visible region with λmax, 1 ranging from 445 to 608 nm. EPR, ENDOR and 2H NMR studies have led to a complete analysis and full assignment of all hyperfine coupling constants. The π-SOMO of 6-oxo-2 and 6-thioxo-verdazyls 3, having nodes at C(3) and C(6), is mainly confined to the nitrogens of the verdazyl ring. Spin delocalization into the N-phenyl groups is reduced, particularly in the 6-thioxoverdazyls, owing to the large torsion angle about the N–C(phenyl) bond.

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Language(s): eng - English
 Dates: 1992-09-021992-10-271993
 Publication Status: Issued
 Pages: 10
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 Rev. Type: Peer
 Identifiers: eDoc: 665117
DOI: 10.1039/P29930000535
Other: 6955
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Title: Journal of the Chemical Society-Perkin Transactions 2
  Other : J. Chem. Soc.-Perkin Trans. 2
Source Genre: Journal
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Publ. Info: Cambridge, England : Royal Society of Chemistry
Pages: - Volume / Issue: 1993 (3) Sequence Number: - Start / End Page: 535 - 544 Identifier: ISSN: 1472-779X
CoNE: https://pure.mpg.de/cone/journals/resource/111053443082010