Contribution of hyperconjugation and inductive effects to the pseudo-anomeric effect in 4-substituted methoxycyclohexanes

Bruno A. Piscelli, David O’Hagan, Rodrigo A. Cormanich*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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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.
Original languageEnglish
Pages (from-to)724–728
Number of pages5
JournalJournal of Physical Chemistry A
Volume127
Issue number3
Early online date17 Jan 2023
DOIs
Publication statusPublished - 26 Jan 2023

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