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Interactive Molecular Model Assembly with 3D Printing
Published on: August 13, 2020
Electronic interactions and their influence on the conformational stability of trans-2-halocyclopentanol
Cláudio F Tormena1, Francisco P Dos Santos, Alvaro Cunha Neto
1Chemistry Institute, State University of Campinas, Caixa Postal 6154, 13084-971 Campinas, SP, Brazil. tormena@iqm.unicamp.br
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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