Electronic interactions and their influence on the conformational stability of trans-2-halocyclopentanol.
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.
Tormena
Cláudio F
CF
Chemistry Institute, State University of Campinas, Caixa Postal 6154, 13084-971 Campinas, SP, Brazil. tormena@iqm.unicamp.br
Santos
Francisco P Dos
FP
Neto
Alvaro Cunha
AC
Rittner
Roberto
R
Yoshinaga
Fabiana
F
Temistocles
Jacqueline C T
JC