NMR Spectroscopic Observation of a Metal‐Free Acetylide Anion | Zendy

Tanaka Yoshiyuki | Zendy; Arakawa Makoto | Zendy; Yamaguchi Yohei | Zendy; Hori Chieko | Zendy; Ueno Masahiro | Zendy; Tanaka Takeyuki | Zendy; Imahori Tatsushi | Zendy; Kondo Yoshinori | Zendy

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NMR Spectroscopic Observation of a Metal‐Free Acetylide Anion

Author(s) -

Tanaka Yoshiyuki,

Arakawa Makoto,

Yamaguchi Yohei,

Hori Chieko,

Ueno Masahiro,

Tanaka Takeyuki,

Imahori Tatsushi,

Kondo Yoshinori

Publication year - 2006

Publication title -

chemistry – an asian journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.18

H-Index - 106

eISSN - 1861-471X

pISSN - 1861-4728

DOI - 10.1002/asia.200600099

Subject(s) - phenylacetylene , deprotonation , carbanion , chemistry , acetylide , alkyne , photochemistry , metal , resonance (particle physics) , nuclear magnetic resonance spectroscopy , medicinal chemistry , inorganic chemistry , ion , stereochemistry , organic chemistry , catalysis , atomic physics , physics

A metal‐free acetylide was observed by using NMR spectroscopy. Metal‐free acetylides are closely related to reactive intermediates (carbanions) in solution; therefore, they have been regarded as unobservable species. However, we generated this highly reactive and unstable species through the deprotonation of phenylacetylene by using the strong nonmetallic phosphazene base t Bu‐P4. In the presence of t Bu‐P4, the J coupling between the ethynyl carbon and hydrogen nuclei ( 1 J C,H ) of phenylacetylene disappeared; this indicates the deprotonation of the alkyne terminal. Furthermore, a large low‐field shift (approximately 90 ppm) of the alkyne carbon resonance was observed. We concluded that we have observed a metal‐free carbanion with a formal charge on an sp‐hybridized carbon atom for the first time.

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