Nonplanar aromatic compounds. 9. Synthesis, structure, and aromaticity of 1:2,13:14-dibenzo[2]paracyclo[2](2,7)-pyrenophane-1,13-diene

Organic Letters

Volumn 10, Issue 2, 2008, Pages 273-276

  Zhang, Baozhong ^a   Manning, Gregory P ^a   Dobrowolski, Michał A ^b   Cyrański, Michał K ^b   Bodwell, Graham J ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38749150658     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702703b     Document Type: Article

References (49)

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32. We prefer the name 1:2,13:14-dibenzo[2]paracyclo-[2](2,7)pyrenophane-1, 13-diene.
33. The cyclic system is shape-persistent, but the size of the cycle (16 atoms) and the small cavity (4.0 Å between the centroid of the central benzene ring and the centroid of the C(10b)-C(10c) bond of the pyrene system) make categorizing it as a macrocycle questionable.
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42. The comformational behavior of these and related compounds will be addressed in a future publication.
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49. (c) NICS was originally defined as the negative value of the absolute shielding computed at the geometric centre of a ring system. Rings with negative NICS values qualify as aromatic, and the more negative the value of NICS become, the more aromatic the rings are.