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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Stereoelectronic Effects in Multivicinal Fluoroalkanes and Conformational Implications

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Author(s):
Simoes, Luis H. [1] ; Cormanich, Rodrigo A. [1]
Total Authors: 2
Affiliation:
[1] Univ Estadual Campinas, Inst Chem, Dept Organ Chem, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2020, n. 4 JAN 2020.
Web of Science Citations: 0
Abstract

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. (AU)

FAPESP's process: 18/03910-1 - Physicochemical studies of fluorinated organic compounds: experimental and theoretical approaches
Grantee:Rodrigo Antonio Cormanich
Support Opportunities: Research Grants - Young Investigators Grants