Conformational stabilization of phthalan: Physical origin of tiny ring-puckering barrier

Sangmi Jeon, Jaebum Choo, Sungwhan Kim, Younghi Kwon, Jin Yeol Kim, Young Il Lee, Hoeil Chung

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The conformational property of phthalan has been investigated using ab initio calculation and natural bond orbital (NBO) analysis methods. Geometry optimizations for the planar (C2v) and puckered (Cs) conformers have been carried out using the HF, B3LYP, and MP methods, and the results indicate that this molecule has a tiny ring-puckering barrier. This barrier appears to be in good agreement with the previous experimental result. NBO analysis shows that the tiny ring-puckering barrier is closely related to the molecular orbital interactions around the C-O bonds of the five-membered ring. The gas-phase infrared and liquid-phase Raman spectra of phthalan and 1,3-benzodioxole have been recorded and analyzed in terms of C2v symmetry. Vibrational frequency calculations using the B3LYP method have also been performed to compare with the spectroscopic data. The B3LYP frequency calculations do a reasonable job of estimating the frequencies.

Original languageEnglish
Pages (from-to)159-167
Number of pages9
JournalJournal of Molecular Structure
Volume609
Issue number1-3
DOIs
StatePublished - 2002 May 30

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Stabilization
Vibrational spectra
Molecular orbitals
Raman scattering
Gases
Infrared radiation
Molecules
Geometry
Liquids
folpet
1,3-benzodioxole

Keywords

  • 1,3-Benzodioxole
  • Natural bond analysis
  • Phthalan
  • Ring-puckering potential energy function
  • Vibrational spectroscopy

Cite this

Jeon, Sangmi ; Choo, Jaebum ; Kim, Sungwhan ; Kwon, Younghi ; Kim, Jin Yeol ; Lee, Young Il ; Chung, Hoeil. / Conformational stabilization of phthalan : Physical origin of tiny ring-puckering barrier. In: Journal of Molecular Structure. 2002 ; Vol. 609, No. 1-3. pp. 159-167.
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Conformational stabilization of phthalan : Physical origin of tiny ring-puckering barrier. / Jeon, Sangmi; Choo, Jaebum; Kim, Sungwhan; Kwon, Younghi; Kim, Jin Yeol; Lee, Young Il; Chung, Hoeil.

In: Journal of Molecular Structure, Vol. 609, No. 1-3, 30.05.2002, p. 159-167.

Research output: Contribution to journalArticle

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T1 - Conformational stabilization of phthalan

T2 - Physical origin of tiny ring-puckering barrier

AU - Jeon, Sangmi

AU - Choo, Jaebum

AU - Kim, Sungwhan

AU - Kwon, Younghi

AU - Kim, Jin Yeol

AU - Lee, Young Il

AU - Chung, Hoeil

PY - 2002/5/30

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