期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 68, 期 23, 页码 8790-8797出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo034906+
关键词
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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.
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