Phospholes with reduced pyramidal character from steric crowding III NMR and X-ray diffraction studies on 1-( 2,4,6-tri-isopropylphenyl)-3-methylphosphole

G. Keglevich, Louis D. Quin, Zsolt Böcskei, György M. Keserü, Rajdeep Kalgutkar, Paul M. Lahti

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

The 2,4,6-tri-isopropylphenyl substituent was placed on the phosphorus of a phosphole to reduce the pyramidal character. That this was accomplished was revealed by single crystal X-ray diffraction analysis; with respect to the plane of C2-P-C5 in the phosphole ring, the ipso carbon of the benzene ring was deflected by only 58.0°, whereas the deflection is 66.9° in the uncrowded 1-benzylphosphole. This proves that the concept of reducing the pyramidal character (with the goal of increasing the electron delocalization) through steric crowding can be realized. In the crystal the two rings are in orthogonal planes, but this relation is not retained in solution; NMR studies show that the two edges of the benzene ring, as well as the 2,6-isopropyl groups, are identical.

Original languageEnglish
Pages (from-to)109-116
Number of pages8
JournalJournal of Organometallic Chemistry
Volume532
Issue number1-2
Publication statusPublished - Apr 1 1997

Fingerprint

crowding
Benzene
X-Ray Diffraction
Nuclear magnetic resonance
X ray diffraction
nuclear magnetic resonance
rings
diffraction
Phosphorus
X ray diffraction analysis
x rays
Carbon
benzene
Single crystals
Electrons
Crystals
phosphorus
deflection
carbon
single crystals

Keywords

  • Aromaticity
  • Bird-index
  • Delocalization
  • Phosphole
  • Single crystal X-ray analysis
  • Stereostructure

ASJC Scopus subject areas

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

Cite this

Phospholes with reduced pyramidal character from steric crowding III NMR and X-ray diffraction studies on 1-( 2,4,6-tri-isopropylphenyl)-3-methylphosphole. / Keglevich, G.; Quin, Louis D.; Böcskei, Zsolt; Keserü, György M.; Kalgutkar, Rajdeep; Lahti, Paul M.

In: Journal of Organometallic Chemistry, Vol. 532, No. 1-2, 01.04.1997, p. 109-116.

Research output: Contribution to journalArticle

Keglevich, G. ; Quin, Louis D. ; Böcskei, Zsolt ; Keserü, György M. ; Kalgutkar, Rajdeep ; Lahti, Paul M. / Phospholes with reduced pyramidal character from steric crowding III NMR and X-ray diffraction studies on 1-( 2,4,6-tri-isopropylphenyl)-3-methylphosphole. In: Journal of Organometallic Chemistry. 1997 ; Vol. 532, No. 1-2. pp. 109-116.
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AU - Böcskei, Zsolt

AU - Keserü, György M.

AU - Kalgutkar, Rajdeep

AU - Lahti, Paul M.

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