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
收藏
页码：1227 / 1232
页数：6
相关论文
共 24 条
123