Stabilizing the hammick intermediate

Oldamur Hollóczki, L. Nyulászi

Research output: Article

26 Citations (Scopus)

Abstract

(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
Volume73
Issue number13
DOIs
Publication statusPublished - júl. 4 2008

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Stabilization
Deprotonation
Birds
Isomers
Substitution reactions
Nitrogen
Carbon
Atoms
pyridine
carbene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stabilizing the hammick intermediate. / Hollóczki, Oldamur; Nyulászi, L.

In: Journal of Organic Chemistry, Vol. 73, No. 13, 04.07.2008, p. 4794-4799.

Research output: Article

Hollóczki, Oldamur ; Nyulászi, L. / Stabilizing the hammick intermediate. In: Journal of Organic Chemistry. 2008 ; Vol. 73, No. 13. pp. 4794-4799.
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