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Origin of cis preference among the three isomers of 1,4‐difluorobutadiene
Author(s) -
Hu HaiRong,
Gong MaoChu,
Tian Anmin,
Wong NingBew
Publication year - 2003
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.10479
Subject(s) - natural bond orbital , atomic orbital , chemistry , gaussian , computational chemistry , preference , molecular orbital , atom (system on chip) , interaction energy , crystallography , molecule , density functional theory , physics , quantum mechanics , mathematics , electron , organic chemistry , statistics , computer science , embedded system
The slight energy differences among the three isomers of 1,4‐difluorobutadiene have been investigated by Gaussian‐3 (G3) theory. The computational results suggest that the Gaussian‐3–Becke's three‐parameter functional (G3B3) theoretical estimates are in good agreement with experimental data. Mulliken population analysis also has been performed to interpret the anomalous equilibrium relationship among these three isomers. Wire mesh contours of the highest occupied molecular orbital (HOMO) orbitals of these isomers help to illustrate the cis effect visually. Natural bond orbital (NBO) analysis indicates that the origin of cis preference among the three isomers may lie in the configurational orientation and the n‐π conjugative interaction between fluorine atom and CC double bond. © 2003 Wiley Periodicals, Inc. Int J Quantum Chem, 2003