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Inter‐ and intra‐molecular hydrogen bonding effects on geminal 15 N, 1 H spin coupling and 15 N chemical shifts in pyridine derivatives
Author(s) -
Holzer W.,
Von Philipsborn W.
Publication year - 1989
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/mrc.1260270602
Subject(s) - chemistry , geminal , hydrogen bond , pyridine , intramolecular force , lone pair , coupling constant , solvent , hydrogen , nitrogen , crystallography , computational chemistry , molecule , stereochemistry , medicinal chemistry , organic chemistry , physics , particle physics
The two‐bond 15 N,H coupling constant in 3,5‐dimethylpyridine was determined in 30 solvents and shown to vary between −11 and −3 Hz. An increasing ability of the solvent to form hydrogen bonds causes a steady decrease in ∣ 2 J ( 15 N,H)∣, which is also observed with some selected pyridine derivatives with intramolecular hydrogen bonds. A linear correlation is found between the positive lone‐pair effect on ∣ 2 J ( 15 N,H)∣ and the decrease in nitrogen shielding.