Premium
Stereoelectronic Effects in Multivicinal Fluoroalkanes and Conformational Implications
Author(s) -
Simões Luís H.,
Cormanich Rodrigo A.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901780
Subject(s) - chemistry , natural bond orbital , hyperconjugation , computational chemistry , atomic orbital , anomeric effect , electrostatics , molecule , stereochemistry , chemical physics , density functional theory , electron , organic chemistry , quantum mechanics , physics
Multivicinal fluoroalkanes is an interesting group of fluorinated compounds whose synthesis have been extensively explored, but it lacks theoretical studies to support and understand experimental evidences about their geometry. This work elucidates the effects that rule multivicinal fluoroalkanes preference for helical character in extended geometries. Molecules chosen as models are all‐ syn and all‐ anti multivicinal fluorinated n‐alkanes containing 4–10 carbon atoms. Natural Bond Orbitals (NBO) calculations point out that the main driving force to helical conformation in multivicinal fluoroalkanes is electrostatics, in opposition to hyperconjugation domination in n‐perfluoroalkanes. Also, these theoretical calculations show F–H attractive interactions as the main important ones in helical stabilization, particularly those at 1,5 relative distance.