Crystal structure and DFT studies of (E)-1-(4-fluorophenyl)-3-(1H-indol-1-yl)-4-styrylazetidin-2-one

被引：8

作者：

Gummidi, Lalitha ^{[1
]}

Kerru, Nagaraju ^{[1
]}

Ibeji, Collins U. ^{[2
]}

Singh, Parvesh ^{[1
]}

机构：

[1] Univ KwaZulu Natal, Sch Chem & Phys, P Bag X54001, ZA-4000 Durban, South Africa

[2] Univ Nigeria, Fac Phys Sci, Dept Pure & Ind Chem, Nsukka 410001, Enugu State, Nigeria

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2019年 / 1187卷

基金：

新加坡国家研究基金会;

关键词：

cis-beta-Lactam; Indole; Exo attack; X-ray crystal structure; DFT studies; DENSITY-FUNCTIONAL THEORY; MOLECULAR DOCKING; DERIVATIVES; MODEL; STEREOSELECTIVITY; COMPLEXES; CONTINUUM; INDOLES; KETENES;

D O I：

10.1016/j.molstruc.2019.03.053

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An unprecedented diasterospecific synthesis of (E)-1-(4 fluorophenyl)-3-(1H-indol-1-yl)-4-styrylazetidin-2-one (3) from Staudinger [2 + 2] cycloaddition reaction between (E)-4-fluoro-N-((E)-3-phenylallylidene)aniline (1) and indole ketene is herein described. The single crystal X-ray structure confirmed that compound 3 (C25H19FN2O) crystallizes in the monoclinic space group C2/c, with Z = 8, and unit cell parameters; a = 32.0225 (5) angstrom, b=7.39970 (10) angstrom, c = 17.4100 (2) angstrom, beta= 108.3010 (10)degrees, V = 3916.75 (10) angstrom(3), Z = 8. Crystal structure 3 shows the absolute cis configuration of the molecule to be C9 (S) and C10 (R). In addition, the structural parameters (bond lengths, bond angles, and torsion angles) and electronic properties of 3 were computed using the B3LYP/6-31 + G (d,p) and M06-2X/6-31 + G (d,p) basis set in ground state. A good correlation (R-2 = 0.9989) between the experimental and theoretical parameters was achieved. (C) 2019 Elsevier B.V. All rights reserved.

引用

页码：50 / 58

页数：9

共 79 条

[1] Crystallographic structure and quantum chemical computations of 1-(3,4-dimethylphenyl)-3-phenyl-5-(4-methoxyphenyl)-2-pyrazoline [J].