Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 23, Pages 8790-8797Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo034906+
Keywords
-
Categories
Ask authors/readers for more resources
1,8-Bis(dimethylethyleneguanidino)naphthalene (DMEGN), the second example of a peralkyl guanidine proton sponge based on the 1,8-naphthalene backbone, was prepared and fully characterized. The crystal structure analysis of monoprotonated DMEGN reveals an unsymmetrical intramolecular hydrogen bridge. A decrease in the basicity with respect to the noncyclic parent 1,8-bis(tetramethylguanidino)naphthalene was found. Nevertheless, a new proton sponge provides a new crossbar in the ladder of highly basic neutral organic compounds. A detailed theoretical study of DMEGN and related cyclic guanidines explains this surprising experimental result. Homodesmotic reactions reveal that the intramolecular hydrogen bond contributes effectively 10 kcal/mol to proton affinity of DMEGN.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available