A new look at the similarities of the conjugative ability and reactivity of -P=C and C=C double bonding

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Abstract

Comparison of π-ionization energies of 28 compounds containing -X=C〈(X = CH, N, P) double bonds reveals a larger similarity between the carbon and phosphorus than between nitrogen and phosphorus containing species. Ring fragmentation reaction heats of the corresponding azaphospholes and azoles show a similar behavior. All of these facts suggest that, although the strength of the -P=C bond is known to be significantly smaller, than that of the C=C or C=N bond, in conjugative interactions -P=C is more comparable to C=C than to N=C π-systems. By using perturbation arguments, earlier observations about the similarities in chemical reactions of the -P=C and C=C bonds are understandable.

Original languageEnglish
Pages (from-to)4011-4015
Number of pages5
JournalJournal of physical chemistry
Volume97
Issue number16
Publication statusPublished - Dec 1 1993

ASJC Scopus subject areas

  • Engineering(all)
  • Physical and Theoretical Chemistry

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