Synthesis, characterization and palladium complex formation of pyridinium- and quinolinium-3-acetylides: mesomeric betaines or betaine-stabilized carbenes?

Smeyanov, Alexey; Namyslo, Jan C.; Hübner, Eike G.; Nieger, Martin; Schmidt, Andreas

doi:10.1016/j.tet.2015.07.053

Cited by 7 publications

(1 citation statement)

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“…Though an extensive structural characterization was performed, no absorption/emission study was reported, possibly due to the stability issue of complexes in solution. Smeyanov et al 372 reported the first Pd(II) complexes 186 (Chart 20) bearing pyridinium-and quinolinium-3-acetylides. Since quinolinium-3-acetylide can be represented by resonance forms of a mesomeric betaine, allenylidenes, and a betaine-stabilized carbene, the determination of the final structure of the complex was quite challenging.…”

Section: Chemical Reviewsmentioning

confidence: 99%

Rise of Conjugated Poly-ynes and Poly(Metalla-ynes): From Design Through Synthesis to Structure–Property Relationships and Applications

et al. 2018

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Conjugated poly-ynes and poly(metalla-ynes) constitute an important class of new materials with potential application in various domains of science. The key factors responsible for the diverse usage of these materials is their intriguing and tunable chemical and photophysical properties. This review highlights fascinating advances made in the field of conjugated organic poly-ynes and poly(metalla-ynes) incorporating group 4-11 metals. This includes several important aspects of conjugated poly-ynes viz. synthetic protocols, bonding, electronic structure, nature of luminescence, structure-property relationships, diverse applications, and concluding remarks. Furthermore, we delineated the future directions and challenges in this particular area of research.

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Section: Chemical Reviewsmentioning

confidence: 99%

Rise of Conjugated Poly-ynes and Poly(Metalla-ynes): From Design Through Synthesis to Structure–Property Relationships and Applications

et al. 2018

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Stable Carbenes or Betaines?

Kleinpeter

Koch

2018

Eur J Org Chem

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The anisotropy effect in 1H NMR spectroscopy can be readily employed to indicate the position of carbene/betaine mesomeric equilibria. NR2 substituted carbene/betaines tend to adopt betaine structures, whereas in the absence of NR2 substituents, the betaine structures cannot stabilise the structure through both π‐donation effects of the NMe2 groups and the electronegativity of the nitrogen atoms, and the corresponding carbene‐like structures are preferred. These conclusions are supported by calculated bond orders and δ(13C)/ppm values. The spatial magnetic properties of isonitriles and carbon monoxide, which can be counted as stable carbenes or, at least, as carbene‐analogues, also exist as stable betaine structures, which is again supported by structural and magnetic properties.

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Six-Membered Ring Systems

Kishbaugh

2016

Progress in Heterocyclic Chemistry

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Synthesis, characterization and palladium complex formation of pyridinium- and quinolinium-3-acetylides: mesomeric betaines or betaine-stabilized carbenes?

Cited by 7 publications

References 50 publications

Rise of Conjugated Poly-ynes and Poly(Metalla-ynes): From Design Through Synthesis to Structure–Property Relationships and Applications

Rise of Conjugated Poly-ynes and Poly(Metalla-ynes): From Design Through Synthesis to Structure–Property Relationships and Applications

Stable Carbenes or Betaines?

Six-Membered Ring Systems

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