N-对-甲苯磺酰-3-乙酰基-吲哚的合成、晶体结构和理论计算(英文)

Synthesis,Crystal Structure and Theoretical Calculation of N-p-Tolylsulfonyl-3-acetyl-indole

N-对-甲苯磺酰-吲哚(1)在二氯甲烷中与乙酰基氯反应得到产率为89%的N-对-甲苯磺酰-3-乙酰基-吲哚(2)(分子式:C17H15NO3S,分子量:313.36),用单晶X-射线衍射方法测定了2的晶体结构并表明:属三斜晶系,空间群为P-1,单胞参数为a=10.026 4(13),b=12.591 3(16),c=14.162 1(18),α=111.933(2)°,β=107.593(2)°,γ=93.675(2)°,V=1 548.9(3)3,Dc=1.344 g/cm3,μ=0.221 mm-1,F(000)=656及Z=4。在化合物2中,吲哚环的9个原子几乎处于同一平面,两个独立分子中的苯基环与吲哚环面所形成的二面角分别是81.1°和95.0°,S-N和S=O的平均键长分别为1.674(4),1.412(4)。此外,在B3LYP/6-31G*水平下用密度泛函理论(DFT)计算化合物2的分子轨道并优化其结构几何。

Treatment of N-p-tolylsulfonylindole 1 with acetyl chloride in dried dichloromethane gave the title compound, N-p-tolylsuffonyl-3-acetyl-indole 2 （C17H15NO3S, Mr=313.36） in 89% yield. Single-crystal structure of 2 was determined by X-ray crystallography.2 crystallizes in the triclinic system, space group P-1 with a=10.026 4（13）,b=12.591 3（16）, c=14.162 1（18） A, α=111.933（2）°, β=107.593（2）°, γ=93.675（2）°,V=1 548.9（3） A^3, Dc=1.344 g/cm^3,μ=0.221 mm^-1, F （000）=656 and Z=4. In the compound, the 9-atom indole ring system is nearly planar, and the dihedral angles formed by the phenyl ring and the indole plane are 81.1°and 95.0°.The average S-N and S=O bond lengths are 1.674（4） and 1.412（4）A, respectively. Molecular orbital calculation using density functional theory （DFT） at B3LYP/631 G＊ level optimized the structural geometry of compound 2.