Topically resolved intramolecular CH-pi interactions in phenylalanine derivatives
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-pi interactions shifted well upfield (delta 5.4-5.8 at -88 degrees 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)).
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2009 |
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| Erschienen: |
2009 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:7 |
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| Enthalten in: |
Organic & biomolecular chemistry - 7(2009), 24 vom: 21. Dez., Seite 5156-62 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Jennings, W Brian [VerfasserIn] |
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| Links: |
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| Themen: |
47E5O17Y3R |
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| Anmerkungen: |
Date Completed 10.05.2010 Date Revised 21.11.2013 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1039/b916021n |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM193884623 |
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| 520 | |a 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-pi interactions shifted well upfield (delta 5.4-5.8 at -88 degrees 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)) | ||
| 650 | 4 | |a Journal Article | |
| 650 | 7 | |a Benzophenones |2 NLM | |
| 650 | 7 | |a Imines |2 NLM | |
| 650 | 7 | |a Nitrogen Oxides |2 NLM | |
| 650 | 7 | |a nitrones |2 NLM | |
| 650 | 7 | |a Phenylalanine |2 NLM | |
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| 700 | 1 | |a McCarthy, Noel J P |e verfasserin |4 aut | |
| 700 | 1 | |a Kelly, Padraig |e verfasserin |4 aut | |
| 700 | 1 | |a Malone, John F |e verfasserin |4 aut | |
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