Stereoelectronic and inductive effects on  1 H and  13 C NMR chemical shifts of some  cis ‐1,3‐disubstituted cyclohexanes | Zendy

de Oliveira Paulo R. | Zendy; Tasic Ljubica | Zendy; Rocco Silvana A. | Zendy; Rittner Roberto | Zendy

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Stereoelectronic and inductive effects on 1 H and 13 C NMR chemical shifts of some cis ‐1,3‐disubstituted cyclohexanes

Author(s) -

de Oliveira Paulo R.,

Tasic Ljubica,

Rocco Silvana A.,

Rittner Roberto

Publication year - 2006

Publication title -

magnetic resonance in chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.483

H-Index - 72

eISSN - 1097-458X

pISSN - 0749-1581

DOI - 10.1002/mrc.1850

Subject(s) - electronegativity , chemistry , substituent , chemical shift , halogen , natural bond orbital , inductive effect , isodesmic reaction , crystallography , stereochemistry , computational chemistry , medicinal chemistry , density functional theory , organic chemistry , alkyl

This work presents the substituent effects on the 1 H and 13 C NMR chemical shifts in the cis ‐isomer of 3‐Y‐cyclohexanols (Y = Cl, Br, I, CH 3 , N(CH 3 ) 2 and OCH 3 ) and 3‐Y‐1‐methoxycyclohexanes (Y = F, Cl, Br, I, CH 3 , N(CH 3 ) 2 and OCH 3 ). It was observed that the H‐3 chemical shift, due to the substituent α‐effect, increases with the increase of substituent electronegativity when Y is from the second row of the periodic table of elements, (CH 3 n O > n F ) with *σ C2C3 , *σ C3C4 and *σ C3H3a in comparison with the same type of interaction with the lone pair of the other halogens. Copyright © 2006 John Wiley & Sons, Ltd.

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