Bruno A Piscelli, D. O'Hagan, Rodrigo A. Cormanich
Jan 17, 2023
Citations
0
Influential Citations
0
Citations
Journal
The journal of physical chemistry. A
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.