Bent structure and dynamic stereochemistry of chiral acridinium cations

Journal of Organic Chemistry

Volumn 68, Issue 16, 2003, Pages 6304-6308

  Laleu, Benoît ^a   Herse, Christelle ^a   Laursen, Bo W ^b   Bernardinelli, Gérald ^a   Lacour, Jérôme ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL BONDS;

BENT STRUCTURE;

POSITIVE IONS;

ACRIDINE DERIVATIVE; AMINE; AROMATIC COMPOUND; CARBON; CATION; NITROGEN; TRITYL DERIVATIVE;

ARTICLE; ATOM; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0041529893     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0345998     Document Type: Article

References (33)

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25. Dealkylation at high temperature of pyridinium salts was observed by Balaban and Katritzky. See ref 6d and references therein.
26. For line-shape analysis, the system was analyzed as a four-site coalescence of four singlets into two singlets.
27. c , and the frequency separation of the peaks, Δv (Hz).
28. 6, compounds 2e and 2f decompose into acridine 3 at 60 and 80 °C, respectively. No such behavior was observed for 2d (T < 150 °C).
29. To the exception of compounds 2e and 2f for which, as could be expected, similar energy values were found, 1-phenyl and 2-naphthyl having similar steric influence.
30. Contrary to 2g for which no stacking interaction was observed, all aromatic moieties of 2d are involved in weak stacking interactions which, to our point-of view, do not affect the deformation of the central pyridinium ring.
31. 3 carbon is in the plane of the pyridine ring. See ref 6.
32. It is likely that bulky nonstereogenic amines (cyclohexy]amine, 9H-fluoren-9-ylamine) will induce similar deformations.
33. Cations 2d-i are effective dyes absorbing light efficiently in most of the visible region (ref 8). Very dilute solutions and restricted wavelengths were required to measure the specific optical rotations.