Anomeric effect plays a major role in the conformational isomerism of fluorinated pnictogen compounds | Zendy

Martins Levindo E. | Zendy; Freitas Matheus P. | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

Anomeric effect plays a major role in the conformational isomerism of fluorinated pnictogen compounds

Author(s) -

Martins Levindo E.,

Freitas Matheus P.

Publication year - 2008

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.1397

Subject(s) - chemistry , anomeric effect , isodesmic reaction , pnictogen , conformational isomerism , vicinal , hyperconjugation , antibonding molecular orbital , lone pair , stereochemistry , crystallography , anomer , computational chemistry , density functional theory , molecule , organic chemistry , atomic orbital , physics , superconductivity , quantum mechanics , electron

According to our theoretical studies, the anomeric effect, an stereoelectronic interaction between lone pair and a vicinal antibonding orbital, has shown to contribute decisively for the conformational isomerism of 1‐fluoro‐ N,N ‐dimethylmethanamine ( 1 ) and of its corresponding P, As and Sb analogues ( 2 – 4 ). CX bonds in 2 – 4 are larger than in the parent compound 1 , thus providing a LP X /CF * interaction progressively weaker on going from 1 to 4 . However, such hyperconjugation contributed by more than 1.3 kcal mol −1 for the stabilization of anti conformer in 4 ( θ LPXCF = 180°), increasing to 24.1 kcal mol −1 in 1 . An isodesmic reaction model supported these findings. Copyright © 2008 John Wiley & Sons, Ltd.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research