Contribution of Hyperconjugation and Inductive Effects to the Pseudo -anomeric Effect in 4-Substituted Methoxycyclohexanes
The Journal of Physical Chemistry A2023Vol. 127(3), pp. 724–728
Citations Over TimeTop 18% of 2023 papers
Abstract
The importance of electrostatic nonconventional hydrogen bonds (NCHBs) to the pseudo-anomeric effect of 4-substituted methoxycyclohexanes is evaluated using theory [natural bond orbital (NBO)] to deconvolute electrostatic from other contributing effects. There is an interesting interplay between σCH → σCX* hyperconjugation and the electropositive charge on 3,5-axial hydrogens (Hax). In essence, better σCX* (or πCO*) acceptors increase the charge on 3,5-CHax, which in turn strengthens Cδ+Hax···δ-OMe NCHB interactions.
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