Theoretical Study of Halogen Effect in Isomerization of 2-Halo-[9]-annulen Anion at the DFT Level |
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| Authors: | AHMADREZA Bekhradnia SATTARArshadi |
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| Affiliation: | 1. Pharmaceutical Sciences Research Center, Department of Medicinal Chemistry, Mazandaran University of Medical Sciences, Sari, Iran
2. Department of Chemistry, Payame Noor University, Behshahr Unit, Behshahr, Iran |
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| Abstract: | Cis-trans isomerization of [9]-annulenanion (1) and its 2-fluoro-, 2-chloro- and 2-bromo-derivatives (2, 3 and 4, respectively) were investigated at the HF/6-31G* and B3LYP/6-311++G** levels of theory. Cis,cis,cis,cis structures appear more stable than their corresponding cis,cis,cis,trans-isomers. The relative height of energy barriers for cis-trans isomerization is: 2cis ＞ 1cis＞ 3cis ＞ 4cis. This trend for the reverse trans-cis isomerization follows the electronegativity of the substituent at C-2 (2trans ＞ 3trans ＞ 4trans ＞ 1trans). |
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| Keywords: | isomerization halogen effects [9]-annulen anion DFT |
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