Study of the planarization of the tricordinate phosphorus in phospholes; Photoelectron spectra and structure of partially planarized phospholes

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35 Citations (Scopus)

Abstract

The gradual flattening of the tricoordinate phosphorus in phosphole by the increasing steric bulk of the substituent group is shown on the HF/6-31G* optimized geometries of alkylarylphospholes. By the decreasing pyramidality, aromaticity indices show increase, as a result of the increased conjugation. The aromaticity of 1-(2,4,6-tri-tertiarybutyl)-phosphole is similar to that of furan according to the geometrical indices. In the photoelectron spectra of the alkylaryl substituted phospholes the phosphorus lone pair ionization energy also decreases along the decreasing pyramidality. 1-(2,4,6-tri-Tertiarybutyl-phenyl)-3-methylphosphole has the lowest ionization energy value ever reported for a phosphole.

Original languageEnglish
Pages (from-to)29-35
Number of pages7
JournalJournal of Organometallic Chemistry
Volume566
Issue number1-2
Publication statusPublished - Sep 15 1998

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Ionization potential
Photoelectrons
Phosphorus
phosphorus
photoelectrons
ionization
furans
flattening
conjugation
Geometry
energy
geometry
furan

Keywords

  • Ab initio calculations
  • Aromaticity
  • Phospholes
  • Photoelectron spectra

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

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abstract = "The gradual flattening of the tricoordinate phosphorus in phosphole by the increasing steric bulk of the substituent group is shown on the HF/6-31G* optimized geometries of alkylarylphospholes. By the decreasing pyramidality, aromaticity indices show increase, as a result of the increased conjugation. The aromaticity of 1-(2,4,6-tri-tertiarybutyl)-phosphole is similar to that of furan according to the geometrical indices. In the photoelectron spectra of the alkylaryl substituted phospholes the phosphorus lone pair ionization energy also decreases along the decreasing pyramidality. 1-(2,4,6-tri-Tertiarybutyl-phenyl)-3-methylphosphole has the lowest ionization energy value ever reported for a phosphole.",
keywords = "Ab initio calculations, Aromaticity, Phospholes, Photoelectron spectra",
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T1 - Study of the planarization of the tricordinate phosphorus in phospholes; Photoelectron spectra and structure of partially planarized phospholes

AU - Nyulászi, László

AU - Soós, László

AU - Keglevich, György

PY - 1998/9/15

Y1 - 1998/9/15

N2 - The gradual flattening of the tricoordinate phosphorus in phosphole by the increasing steric bulk of the substituent group is shown on the HF/6-31G* optimized geometries of alkylarylphospholes. By the decreasing pyramidality, aromaticity indices show increase, as a result of the increased conjugation. The aromaticity of 1-(2,4,6-tri-tertiarybutyl)-phosphole is similar to that of furan according to the geometrical indices. In the photoelectron spectra of the alkylaryl substituted phospholes the phosphorus lone pair ionization energy also decreases along the decreasing pyramidality. 1-(2,4,6-tri-Tertiarybutyl-phenyl)-3-methylphosphole has the lowest ionization energy value ever reported for a phosphole.

AB - The gradual flattening of the tricoordinate phosphorus in phosphole by the increasing steric bulk of the substituent group is shown on the HF/6-31G* optimized geometries of alkylarylphospholes. By the decreasing pyramidality, aromaticity indices show increase, as a result of the increased conjugation. The aromaticity of 1-(2,4,6-tri-tertiarybutyl)-phosphole is similar to that of furan according to the geometrical indices. In the photoelectron spectra of the alkylaryl substituted phospholes the phosphorus lone pair ionization energy also decreases along the decreasing pyramidality. 1-(2,4,6-tri-Tertiarybutyl-phenyl)-3-methylphosphole has the lowest ionization energy value ever reported for a phosphole.

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KW - Aromaticity

KW - Phospholes

KW - Photoelectron spectra

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