IRIS publication 43334542
Topically resolved intramolecular CH-pi interactions in phenylalanine derivatives
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TY - JOUR - Jennings, WB,McCarthy, NJP,Kelly, P,Malone, JF - 2009 - September - Organic ; Biomolecular Chemistry - Topically resolved intramolecular CH-pi interactions in phenylalanine derivatives - Validated - () - FACE AROMATIC INTERACTIONS DOUBLE-MUTANT CYCLES MOLECULAR RECOGNITION BENZENE DIMER CONFORMATIONAL-ANALYSIS ARENE INTERACTIONS BINDING COMPLEXATION CHEMISTRY BALANCE - 7 - 5156 - 5162 - 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)). - DOI 10.1039/b916021n DA - 2009/09 ER -
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@article{V43334542, = {Jennings, WB and McCarthy, NJP and Kelly, P and Malone, JF }, = {2009}, = {September}, = {Organic ; Biomolecular Chemistry}, = {Topically resolved intramolecular CH-pi interactions in phenylalanine derivatives}, = {Validated}, = {()}, = {FACE AROMATIC INTERACTIONS DOUBLE-MUTANT CYCLES MOLECULAR RECOGNITION BENZENE DIMER CONFORMATIONAL-ANALYSIS ARENE INTERACTIONS BINDING COMPLEXATION CHEMISTRY BALANCE}, = {7}, pages = {5156--5162}, = {{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)).}}, = {DOI 10.1039/b916021n}, source = {IRIS} }
Data as stored in IRIS
AUTHORS | Jennings, WB,McCarthy, NJP,Kelly, P,Malone, JF | ||
YEAR | 2009 | ||
MONTH | September | ||
JOURNAL_CODE | Organic ; Biomolecular Chemistry | ||
TITLE | Topically resolved intramolecular CH-pi interactions in phenylalanine derivatives | ||
STATUS | Validated | ||
TIMES_CITED | () | ||
SEARCH_KEYWORD | FACE AROMATIC INTERACTIONS DOUBLE-MUTANT CYCLES MOLECULAR RECOGNITION BENZENE DIMER CONFORMATIONAL-ANALYSIS ARENE INTERACTIONS BINDING COMPLEXATION CHEMISTRY BALANCE | ||
VOLUME | 7 | ||
ISSUE | |||
START_PAGE | 5156 | ||
END_PAGE | 5162 | ||
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-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)). | ||
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DOI_LINK | DOI 10.1039/b916021n | ||
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