N ‐Carbeniopyridinium salts: Charge‐transfer complexes with the C 5  (COOMe) 5  anion; CC bond formation with the TCNQ radical anion | Zendy

Maas Gerhard | Zendy; Weber Hans Martin | Zendy; Exner Reiner | Zendy; Salbeck Josef | Zendy

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N ‐Carbeniopyridinium salts: Charge‐transfer complexes with the C 5 (COOMe) 5 anion; CC bond formation with the TCNQ radical anion

Author(s) -

Maas Gerhard,

Weber Hans Martin,

Exner Reiner,

Salbeck Josef

Publication year - 1990

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.610030708

Subject(s) - pyridinium , chemistry , dication , tetrafluoroborate , medicinal chemistry , pyridinium compounds , ion , organic anion , hydrate , crystal structure , stereochemistry , crystallography , ionic liquid , organic chemistry , catalysis

N ‐[2,3‐Bis(dimethylamino)cyclopropenylio]‐ and N ‐(tetramethylamidinio)pyridinium salts (trifluoromethanesulphonates and tetrafluoroborates) form 1:1 and 1:2 charge‐transfer complexes with the pentakis(methoxycarbonyl)cyclopentadienide anion. The x‐ray crystal structures of 1‐[2,3‐bis(dimethylamino)cyclopropenylio] pyridinium pentakis(methoxycarbonyl)cyclopentadienide tetrafluoroborate hydrate and of 1‐[2,3‐bis(dimethylamino)cyclopropenylio] pyridinium bis[pentakis(methoxycarbonyl)cyclopentadienide] were determined. In constrast, the tetra‐cyano‐ p ‐quinodimethane (TCNQ) radical anion reacts with the first‐mentioned salts by CC bond formation to give novel dicationic salts. Thereby, the radical anion attacks the pyridinium γ‐position of the N ‐(tetramethylamidinio)‐pyridinium dication, but the three‐membered ring of the N ‐[2,3‐bis(dimethylamino)cyclopropenylio] pyridinium system.

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