Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols

被引：11

作者：

de Rezende, Fatima M. P. ^{[1
]}

Moreira, Marilua A. ^{[1
]}

Cormanich, Rodrigo A. ^{[2
]}

Freitas, Matheus P. ^{[1
]}

机构：

[1] Univ Fed Lavras, Dept Chem, BR-37200000 Lavras, MG, Brazil

[2] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP, Brazil

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 8卷

基金：

巴西圣保罗研究基金会;

关键词：

conformational analysis; 2-fluorobicyclo[2.2.1]heptan-7-ols; hydrogen bond; (1h)J(F; H(O)) coupling constant; quantum-chemical calculations; HYDROGEN-BOND; MOLECULAR-STRUCTURE;

D O I：

10.3762/bjoc.8.137

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four diastereoisomers of 2-fluorobicyclo[2.2.1]heptan-7-ols were computationally investigated by using quantum-chemical calculations, and their relative energies were analyzed on the basis of stereoelectronic interactions, particularly the presence or otherwise of the F center dot center dot center dot HO intramolecular hydrogen bond in the syn-exo isomer. It was found through NBO and AIM analyses that such an interaction contributes to structural stabilization and that the (1h)J(F),(H(O)) coupling constant in the syn-exo isomer is modulated by the n(F)->sigma*(OH) interaction, i.e., the quantum nature of the F center dot center dot center dot HO hydrogen bond.

引用

页码：1227 / 1232

页数：6

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