Stabilizing the hammick intermediate

Oldamur Hollóczki, László Nyulászi

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(Figure Presented) The possible stabilization of pyridine-2-ylidene has been investigated at B3LYP/6-31+G* and B3LYP/6-311+G** levels of theory. The aromaticity of this compound is a significant contributor to its stability (ISEc = 24-27 kcal mol-1, Bird index = 77, NICS(0) = -6.8 ppm, NICS(1) = -9.1 ppm; all about 80% of those for the H-shift isomer pyridine). The stabilization energy of the carbene (measured by an appropriate isodesmic reaction) can be influenced by the substitution at nitrogen with bulky groups, and at the carbon atom by amino groups. Considering possible competitive deprotonation reactions of the most likely synthetic route, 1j, 1k, and 1L are suggested as synthesizeable new stable carbenes.

Original languageEnglish
Pages (from-to)4794-4799
Number of pages6
JournalJournal of Organic Chemistry
Issue number13
Publication statusPublished - Jul 4 2008


ASJC Scopus subject areas

  • Organic Chemistry

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