Iminophosphorane-substituted proton sponges. Part 4. Comparison of X-ray molecular structures with solution properties (pKa,1H and13C NMR spectroscopy)
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 709-713
- https://doi.org/10.1039/p29930000709
Abstract
Classical ‘proton sponges’ related to 1,8-bis(dimethylamino) naphthalene (DMAN) and new ones derived from the replacement of one or both dimethylamino groups by iminophosphorane groups are compared (i) in the solid state using crystallographic data, (ii) in solution in deuteriochloroform and [2H6]dimethyl sulfoxide by 1H and 13C NMR spectroscopy, (iii) in water and ethanol–water mixtures by determining their pKa′ s. The conclusion is that the new sponges are stronger than the classical ones but, since they decompose when the acid proton is removed are of no practical value as chemical reagents.Keywords
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