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Issue 24, 2009
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Topically resolved intramolecular CH-π interactions in phenylalanine derivatives

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Abstract

NMR spectra of imines and nitrones derived from benzophenone and phenylalanine or tyrosine show clear evidence of an aromatic edge-to-face interaction in solution. At low temperatures the two ortho protons of the edge interacting phenyl ring become topically resolved with the ortho proton NMR signal involved in the CH-π interactions shifted well upfield (δ 5.4–5.8 at −88 °C) of the other ortho signal. Introduction of a para substituent into the phenylalanine ring has a modest effect on the upfield shift. The edge-to-face arrangement also manifests in the X-ray crystal structures of two of these compounds. Barriers to rotation around the syn phenyl-imino bond are also reported (10.5–11.1 kcal mol−1).

Graphical abstract: Topically resolved intramolecular CH-π interactions in phenylalanine derivatives

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Publication details

The article was received on 04 Aug 2009, accepted on 24 Sep 2009 and first published on 27 Oct 2009


Article type: Paper
DOI: 10.1039/B916021N
Citation: Org. Biomol. Chem., 2009,7, 5156-5162

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    Topically resolved intramolecular CH-π interactions in phenylalanine derivatives

    W. B. Jennings, N. J. P. McCarthy, P. Kelly and J. F. Malone, Org. Biomol. Chem., 2009, 7, 5156
    DOI: 10.1039/B916021N

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