کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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216029 | 1426261 | 2012 | 14 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: The quinones of bicyclo[3.1.0]hexatriene: A computational study of their chemistry and thermochemistry The quinones of bicyclo[3.1.0]hexatriene: A computational study of their chemistry and thermochemistry](/preview/png/216029.png)
Quinones of bicyclo[3.1.0]hexa-1,3,5-triene were examined computationally. The six compounds considered were the five possible classical and one non-classical quinone: bicyclo[3.1.0]hexa-1(6),4-diene-2,3-dione (and its monocyclic isomer with a long trans-annular bond), bicyclo[3.1.0]hexa-1(5),3-diene-2,6-dione, bicyclo[3.1.0]hexa-1,4-diene-3,6-dione (and its monocyclic isomer with a long trans-annular bond), and bicyclo[3.1.0]hexa-1(5),4-diene-2,4-dione-3,6-diyl, a non-classical (non-Kekulé) zwitterion. The two long trans-annular bond structures are akin to that found for m-benzyne. Geometries were calculated (BLYP/6-31G∗, CASSCF(2,2)/6-31G∗, MP2/6-31G∗) and electronic structural inferences were made from the geometries. Also calculated were relative energies and heats of formation (CBS-QB3), singlet and triplet energies (BLYP/6-31G∗), and ionization energies and electron affinities (HF/6-311+G∗∗//BLYP/6-31G∗). The NICS(1) calculations were performed as a probe of the aromaticity of the diverse quinones.
Figure optionsDownload as PowerPoint slideHighlights
► Five new bicyclo[3.1.0]hexa-1,3,5-triene quinones are explored quantum chemically.
► A nonclassical zwitterionic quinone of reasonable stability is uncovered.
► Shortbond-long bond isomerism is exhibited.
Journal: The Journal of Chemical Thermodynamics - Volume 52, September 2012, Pages 43–56