The NH---FC dipole orientation effect for pendant exocyclic CH2F

被引：35

作者：

Lankin, DC

Grunewald, GL

Romero, FA

Oren, IY

Snyder, JP

机构：

[1] Pharmacia Corp, Skokie, IL 60077 USA

[2] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA

[3] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 21期

关键词：

D O I：

10.1021/ol026358c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] DFT and MMFF force field calculations for 2 (R = H) predict that two conformers dominate in water ( greater than or equal to95%) and both sustain a geometry in which the C-F and H-N dipoles align oppositely in a near-planar arrangement. The H-1 NMR spectra (D2O and DMSO-d(6)) and X-ray structure for 2 (R = SO2NHEt) confirm the predictions in all essentials. A novel single-conformer system is proposed.

引用

页码：3557 / 3560

页数：4

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