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New Element‐Carbon (p‐p)π Bonds
Author(s) -
Jutzi Peter
Publication year - 1975
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197502321
Subject(s) - double bond , chemistry , carbon fibers , benzene , naphthalene , main group element , boron , anthracene , inorganic chemistry , computational chemistry , organic chemistry , materials science , transition metal , composite material , catalysis , composite number
Recent years have seen the preparation of π systems containing novel (p‐p)π bonds between carbon and elements from the third, fourth, and fifth Main Groups of the Periodic Table; most of these compounds are predicted to be incapable of existence according to the classical concepts of the double bond. (p‐p)π. Bonds between carbon and phosphorus, arsenic, and antimony have been successfully stabilized in resonance‐stabilized colored compounds of the cyanine and triphenylmethane type, and also in aromatic systems deriving from benzene, naphthalene, and anthracene. Bismuth‐carbon and boron‐carbon (p‐p)π bonds have likewise been confirmed in aromatic systems. Silicon‐carbon and germanium‐carbon (p‐p)π bonds have been detected in extremely reactive derivatives of silaethylene and germaethylene, respectively. The present report describes characteristic reactions of the new π systems. Their bonding follows from X‐ray structure analysis, from photoelectron, UV, and NMR spectra, and from calculations. Criteria for the existence of π systems which are not allowed by the classical double bond rule are discussed; these criteria remain valid on generalization.