Electronic Interactions and Their Influence on the Conformational Stability of trans-2-Halocyclopentanol

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...

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Veröffentlicht in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2007-01, Vol.111 (2), p.295-298
Hauptverfasser: Tormena, Cláudio F, dos Santos, Francisco P, Neto, Alvaro Cunha, Rittner, Roberto, Yoshinaga, Fabiana, Temistocles, Jacqueline C. T
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container_end_page 298
container_issue 2
container_start_page 295
container_title The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory
container_volume 111
creator Tormena, Cláudio F
dos Santos, Francisco P
Neto, Alvaro Cunha
Rittner, Roberto
Yoshinaga, Fabiana
Temistocles, Jacqueline C. T
description 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.
doi_str_mv 10.1021/jp066026f
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title Electronic Interactions and Their Influence on the Conformational Stability of trans-2-Halocyclopentanol
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