Chiral Symmetry Breaking of Axially Chiral Nicotinamide by Crystallization from the Melt

被引：6

作者：

Yagishita, Fumitoshi ^{[1
,2
]}

Okamoto, Kazuma ^{[1
]}

Kamataki, Norifumi ^{[1
]}

Kanno, Shota ^{[1
]}

Mino, Takashi ^{[1
]}

Kasashima, Yoshio ^{[3
]}

Sakamoto, Masami ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Engn, Dept Appl Chem & Biotechnol, Inage Ku, Chiba 2638522, Japan

[2] Chiba Univ, Ctr Analyt Instrumentat, Inage Ku, Chiba 2638522, Japan

[3] Chiba Inst Technol, Fac Engn, Educ Ctr, Narashino, Chiba 2750023, Japan

来源：

CHEMISTRY LETTERS | 2013年 / 42卷 / 12期

关键词：

MODELS; RESOLUTION; CATALYST;

D O I：

10.1246/cl.130796

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

One of six 2-alkylamino-4,6-dimethylnicotinamides afforded a conglomerate, and subsequent X-ray crystallographic analysis revealed that the compound crystallized in the monoclinic system, the space group P2(1). Crystallization of the racemic nicotinamide from the melt led to the chiral breaking of symmetry from 83 to 92% ee. This amide exhibited considerably stable axial Chirality (Delta G(double dagger): 22.4-23.5 kcal mol(-1) at 20 degrees C) due-to rotationally restricted scaffolds for the C C(=O) bond.

引用

页码：1508 / 1510

页数：3

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