Nature of Bonding in Cyclic Conjugated Ylides

and, László Nyulászi; Veszprémi, Tamás

doi:10.1021/jp951740a

Cited by 64 publications

(61 citation statements)

References 37 publications

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“…[224] The extent of aromaticity in phosphinine was initially evaluated as being 88 % of that of benzene [225] but more recent calculations (employing bond separation and homodesmic reaction energies) suggest it to be about 97 %. [226] l 5 Phosphinines, whilst behaving like delocalized cyclic ylids, have similar degrees of aromatic stabilization. [226] From a structural standpoint, it seems that the most reliable structural data come from theoretical studies [226,227] which give bond lengths of PÀC 1.739, C a ÀC b 1.393, C b ÀC g 1.396 .…”

Section: H 4 P]mentioning

confidence: 99%

“…[226] l 5 Phosphinines, whilst behaving like delocalized cyclic ylids, have similar degrees of aromatic stabilization. [226] From a structural standpoint, it seems that the most reliable structural data come from theoretical studies [226,227] which give bond lengths of PÀC 1.739, C a ÀC b 1.393, C b ÀC g 1.396 . As can be seen, the bond-length equalization within the carbon framework is almost perfect.…”

Section: H 4 P]mentioning

confidence: 99%

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Phospha‐Organic Chemistry: Panorama and Perspectives

2003

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Since the beginning of the seventies, organophosphorus chemistry has been completely rejuvenated by the discovery of stable derivatives in which phosphorus has the coordination numbers one or two. The chemistry of these compounds mimics the chemistry of their all-carbon analogues. In this Review article this analogy is discussed for the phosphorus counterparts of alkenes, alkynes, and carbenes. In each case, the synthesis, reactivity, and coordination modes are briefly examined. Some special electronic configurations are also discussed, which include one-electron Pbond;P bonds, strained bonds, and aromatic systems. To conclude, some potential applications of this chemistry in the areas of molecular materials and homogeneous catalysis are presented.

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Section: H 4 P]mentioning

confidence: 99%

Section: H 4 P]mentioning

confidence: 99%

Phospha‐Organic Chemistry: Panorama and Perspectives

2003

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“…[32] Interestingly,s uch buildingb locks also show significant interactions in conjugated p systems, resulting in significant stabilisation energies. [33] We, and others, showed that chemical modifications and coordination to transition metals of a s 3 ,l 3 -P centre [34] was apowerful methodt od evelop new functional p-conjugated molecules.…”

Section: Introductionmentioning

confidence: 99%

Phosphorus‐Containing Polycyclic Aromatic Hydrocarbons

et al. 2017

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Polycyclic aromatic hydrocarbons (PAHs) are highly appealing functional materials in the field of molecular electronics. In particular, molecular engineering of these derivatives by using organic chemistry is a powerful method to tune their properties from the point of view of the band gap and supramolecular assemblies. Another way to achieve such control is to take advantage of the specific reactivity of heteroatoms placed within the sp2‐carbon framework. This strategy has been successfully applied to nitrogen, sulfur and boron. In this review, examples of phosphorus‐containing PAHs and the effect of the phosphorus environment on the electronic properties from both experimental and theoretical points of view are discussed.

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“…[29] Weitere Untersuchungen zum Verhalten von 3 in Additions-und Eliminierungsreaktionen sowie zur Substitution der Seitengruppe N(Alkyl) 2 unter Erhaltung der PH-Funktionalität sind im Gange. …”

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