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Reinvestigation of the substituent effects of fluorine on the 1 H NMR chemical shifts of the adjacent methylene group in fluorinated [2.2]paracyclophanes
Author(s) -
Ernst Ludger,
Ibrom Kerstin
Publication year - 1999
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199906)37:6<441::aid-mrc474>3.0.co;2-8
Subject(s) - chemistry , substituent , methylene , methylene bridge , fluorine , chemical shift , group (periodic table) , stereochemistry , fluorine 19 nmr , two dimensional nuclear magnetic resonance spectroscopy , ring (chemistry) , medicinal chemistry , nuclear magnetic resonance spectroscopy , organic chemistry
of a fluorine substituent into an aromatic ring of [2.2]paracyclophane causes distinct shielding and deshielding effects at the anti ‐ and syn ‐protons, respectively, of the adjacent bridge methylene group. A recent contradictory claim in the literature was disproved by 2D H,H‐NOESY, long‐range H,H‐COSY and H,C‐HMBC experiments. Copyright © 1999 John Wiley & Sons, Ltd.