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Quaternization of imidazoline: Unequivocal structure proof
Author(s) -
Trivedi B. C.,
Digioia A. J.,
Menardi P. J.
Publication year - 1981
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02899469
Subject(s) - delocalized electron , chemistry , proton , imidazoline receptor , product (mathematics) , nuclear magnetic resonance spectroscopy , resonance (particle physics) , spectroscopy , computational chemistry , stereochemistry , organic chemistry , atomic physics , physics , quantum mechanics , mathematics , geometry , medicine
Two structures are possible for the product of quaternization of an N‐alkylimidazoline, i.e., symmetrical and unsymmetrical. The literature employs both versions, with no unambiguous proof available for either. Proton and 13 C nuclear magnetic resonance spectroscopy have been used in this work. The product of quaternization under neutral conditions is shown to be symmetrical. This can be easily rationalized on the basis of resonance stabilization caused by delocalization of the positive charge.