Molecular Geometry and Circular Dichroism Spectra of Bicyclo[2.2.1]heptane-2,3-dicarboxylic Anhydrides and Imides
Authors:
- Tadeusz Połoński,
- Maria J. Milewska,
- Maria Gdaniec,
- Mirosław Gilski
Abstract
Several tricyclic anhydrides and imides derived from optically active bicyclo[2.2.1]heptane-2,3-dicarboxylic acids Were synthesized, and their circular dichroism spectra are reported. On the basis of MNDO calculations it was estalished that despite rigidity of the norbornane system the five-membered rings of succinic anhydride and imide moieties are slightly twisted. The chromophores are flexible and can be more or less skewed depending on solvent polarity. The chromophore nonplanarity significantly influences magnitude and sign of the first Cotton effect associated with the lowest energy n-π* electronic transition. The sign of the second n-π* Cotton effect is governed by vicinal effect of substituents. The crystal structures of three N-(S)-1-phenylethylimides were solved to establish the configuration at C-2 of the imide moieties. © 1993, American Chemical Society. All rights reserved.
- Record ID
- UAM3d630c6b685641439266099fce4bf867
- Author
- Journal series
- Journal of Organic Chemistry, ISSN 0022-3263
- Issue year
- 1993
- Vol
- 58
- No
- 11
- Pages
- 3134-3139
- ASJC Classification
- DOI
- DOI:10.1021/jo00063a038 Opening in a new tab
- URL
- https://pubs.acs.org/doi/abs/10.1021/jo00063a038 Opening in a new tab
- Language
- (en) English
- Score (nominal)
- 0
- Score source
- journalList
- Publication indicators
- = 13; = 14; : 1999 = 1.322; : 2006 (2 years) = 3.790 - 2007 (5 years) =3.716
- Uniform Resource Identifier
- https://researchportal.amu.edu.pl/info/article/UAM3d630c6b685641439266099fce4bf867/
- URN
urn:amu-prod:UAM3d630c6b685641439266099fce4bf867
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or PerishOpening in a new tab system.