Electronic interactions and their influence on the conformational stability of trans-2-halocyclopentanol |
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Authors: | Tormena Cláudio F Santos Francisco P Dos Neto Alvaro Cunha Rittner Roberto Yoshinaga Fabiana Temistocles Jacqueline C T |
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Institution: | Chemistry Institute, State University of Campinas, Caixa Postal 6154, 13084-971 Campinas, SP, Brazil. tormena@iqm.unicamp.br |
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Abstract: | Conformational preferences and electronic interactions of trans-2-fluorocyclopentanol (1), trans-2-chlorocyclopentanol (2), and trans-2-bromocyclopentanol (3) were analyzed using experimental and theoretical (3)J(HH) coupling constants, theoretical calculations, and natural bond orbital (NBO) analysis. The conformational equilibria of compounds 1-3 can be represented by their diaxial and diequatorial conformers as supported by theoretical calculations. From (3)J(HH) coupling constant values, it can be found that the diequatorial conformer is present in the equilibrium as 55% for compound 1 and as 60% for compounds 2 and 3. This behavior is in agreement with orbital interaction analyses obtained from NBO. |
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