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 language | English |
|---|---|
| Pages (from-to) | 159-167 |
| Number of pages | 9 |
| Journal | Journal of Molecular Structure |
| Volume | 609 |
| Issue number | 1-3 |
| DOIs | |
| State | Published - 2002 May 30 |
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Keywords
- 1,3-Benzodioxole
- Natural bond analysis
- Phthalan
- Ring-puckering potential energy function
- Vibrational spectroscopy
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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 journal › Article
TY - JOUR
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
Y1 - 2002/5/30
N2 - 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.
AB - 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.
KW - 1,3-Benzodioxole
KW - Natural bond analysis
KW - Phthalan
KW - Ring-puckering potential energy function
KW - Vibrational spectroscopy
UR - http://www.scopus.com/inward/record.url?scp=0037198478&partnerID=8YFLogxK
U2 - 10.1016/S0022-2860(01)00968-1
DO - 10.1016/S0022-2860(01)00968-1
M3 - Article
AN - SCOPUS:0037198478
VL - 609
SP - 159
EP - 167
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
SN - 0022-2860
IS - 1-3
ER -