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Hydrogen bonding and tautomerism of benzylideneanilines in the solid state
Author(s) -
Maciejewska Dorota,
Pawlak Dorota,
Koleva Vera
Publication year - 1999
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199912)12:12<875::aid-poc213>3.0.co;2-t
Subject(s) - tautomer , chemistry , hydrogen bond , intermolecular force , magic angle spinning , crystallography , molecule , aniline , solid state , computational chemistry , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry
The 13 C cross‐polarization magic angle spinning NMR spectra of N ‐(2′‐hydroxybenzylidene)‐2‐hydroxyaniline ( 1 ), N ‐(2′‐hydroxybenzylidene)‐4‐nitroaniline ( 2 ) and N ‐(4′‐dimethylaminobenzylidene)‐2‐hydroxy‐aniline ( 3 ) indicate a keto–hydroxy tautomerism of 1 but not of 2 . This was confirmed by a single‐crystal x‐ray diffraction study of 1 , which revealed that the two distinct molecules in the unit cell are linked by intermolecular hydrogen bonding. The presence of this bonding may explain the occurrence of the keto–hydroxy tautomerism. Copyright © 1999 John Wiley & Sons, Ltd.