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The structures of two aldazines: [1,1′‐(1 E ,1′ E )‐hydrazine‐1,2‐diylidenebis(methan‐1‐yl‐1‐ylidene)dinaphthalen‐2‐ol] (Lumogen) and 2,2′‐(1 E ,1′ E )‐hydrazine‐1,2‐diylidenebis(methan‐1‐yl‐1‐ylidene)diphenol (salicylaldazine) in the solid state and in solution
Author(s) -
Silva Artur M. S.,
Silva Vera L. M.,
Claramunt Rosa M.,
María Dolores Santa,
Ferraro Marta B.,
Reviriego Felipe,
Alkorta Ibon,
Elguero José
Publication year - 2013
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.3983
Subject(s) - tautomer , chemistry , azine , hydrazone , density functional theory , computational chemistry , dimethyl sulfoxide , keto–enol tautomerism , deuterium , nuclear magnetic resonance spectroscopy , sulfoxide , stereochemistry , medicinal chemistry , organic chemistry , quantum mechanics , physics
A combination of NMR spectroscopy and theoretical methods Density functional theory including dispersion corrections (DFT‐D) was used to study the structures of Lumogen and salicylaldazine. In the solid state, Lumogen exists as the dihydroxy tautomer 1a (an azine, CN–NC) as was already known from an X‐ray determination. In a deuterated dimethyl sulfoxide solution, another tautomer is observed besides 1a; its structure corresponds to the hydroxy‐oxo tautomer 1b (a hydrazone, CN–NH–Csp 2 ). In what concerns salicylaldazine, we have observed only the dihydroxy tautomer 2a. Copyright © 2013 John Wiley & Sons, Ltd.