Advances towards aromatic oligoamide foldamers: synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains
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We have efficiently synthesized 36 arylopeptoid dimers with ortho-, meta-, and para-substituted aromatic backbones and tert-butyl or phenyl side chains. The dimers were synthesized by using a "submonomer method" on solid phase, by applying a simplified common set of reaction conditions. X-ray crystallographic analysis of two of these dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a comparatively more closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone. Investigation of the X-ray structures of two arylopeptoid dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone.
Originalsprog | Engelsk |
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Tidsskrift | European Journal of Organic Chemistry |
Vol/bind | 2014 |
Udgave nummer | 19 |
Sider (fra-til) | 3971-3975 |
Antal sider | 5 |
ISSN | 1434-193X |
DOI | |
Status | Udgivet - 2014 |
ID: 127672067