|Table of Contents|

[1] Cheng Jinjin, Ge Yuhua,. Syntheses and calculation of(E)-4-chloro-4’-ethoxystilbeneand(E)-4, 4’-dichlorostilbene [J]. Journal of Southeast University (English Edition), 2018, (3): 408-414. [doi:10.3969/j.issn.1003-7985.2018.03.018]

Syntheses and calculation of(E)-4-chloro-4’-ethoxystilbeneand(E)-4, 4’-dichlorostilbene()

Journal of Southeast University (English Edition)[ISSN:1003-7985/CN:32-1325/N]

2018 3
Research Field:
Chemistry and Chemical Engineering
Publishing date:


Syntheses and calculation of(E)-4-chloro-4’-ethoxystilbeneand(E)-4, 4’-dichlorostilbene
Cheng Jinjin Ge Yuhua
College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, China
1 2-diphenylethylene crystal structure density functional theory synthesis
(E)-4-chloro-4’-ethoxystilbene(2a)and(E)-4, 4’-dichlorostilbene(2b)were synthesized by the Witting-Horner reaction. The crystals of 2a and 2b were prepared through solvent evaporation and characterized by the single-crystal X-ray diffraction. Molecular structure analysis confirms the E-configuration of CC bond. The crystal of 2a reveals an orthorhombic and space group Pna21 structure while 2b shows a monoclinic and space group P21/c structure. The electronic structures of 2a and 2b were optimized at B3LYP/6-311++G(d, p)level. The Hirshfeld surface and fingerprint plot indicate close O—H and Cl—H contacts and π—π stacking in 2a and 2b. Molecular electrostatic potential shows that the O and Cl atoms of 2a and Cl atoms of 2b have the minimum energies and they are more likely to be attacked by electrophiles in reaction. Frontier molecular orbitals analysis demonstrates that the ΔELUMO-HOMO of 2a and 2b are 3.85 and 3.91 eV, respectively.


[1] Menezes da Silva V H, de Lima Batista A P, Navarro O, et al. Theoretical study on selectivity trends in(N-heterocyclic carbene)-Pd catalyzed mizoroki-heck reactions: Exploring density functionals methods and molecular models [J]. Journal of Computational Chemistry, 2017, 38(28): 2371-2377. DOI: 10.1002/jcc.24867. DOI:10.1002/jcc.24867.
[2] Sirick A, Lednev S, Moskalenko I, et al. Kinetic features of chain initiation reactions during the oxidation of unsaturated compounds in media of different polarity [J]. Reaction Kinetics Mechanisms and Catalysis, 2015, 117(2): 405-415. DOI:10.1007/s11144-015-0957-6.
[3] Xu B, Fang H H, Chen F P, et al. Synthesis, characterization, two-photon absorption, and optical limiting properties of triphenylamine-based dendrimers [J]. New Journal of Chemistry, 2009, 33(12): 2457. DOI:10.1039/b9nj00393b.
[4] Xu H J, Zhao Y Q, Zhou X F. Palladium-catalyzed Heck reaction of aryl chlorides under mild conditions promoted by organic ionic bases[J]. The Journal of Organic Chemistry, 2011, 76(19): 8036-8041. DOI:10.1021/jo201196a.
[5] Li X B, Wang L, Zhang X Q, et al. A highly stereoselective synthesis of stilbenes under solvent-free conditions[J]. Journal of Chemical Research, 2010, 34(9): 489-492. DOI:10.3184/030823410x12814419570511.
[6] Thompson C M, Orellana M D, Lloyd S E, et al. Stereospecific synthesis of cis-stilbenes from benzaldehydes and phenylacetic acids via sequential Perkin condensation and decarboxylation [J]. Tetrahedron Letters, 2016, 57(43): 4866-4868. DOI:10.1016/j.tetlet.2016.09.069.
[7] Roman B I, de Coen L M, Mortier S T F C, et al. Design, synthesis and structure-activity relationships of some novel, highly potent anti-invasive(E)-and(Z)-stilbenes[J]. Bioorganic & Medicinal Chemistry, 2013, 21(17): 5054-5063. DOI:10.1016/j.bmc.2013.06.048.
[8] Hosna S, Janzen D E, Rzaigui M, et al. Synthesis, structural characterization, spectroscopic, thermal, dielectric and Hirshfeld surface analysis of 1-(2-methoxyphenyl)piperazinium chloranilate [J]. Phase Transitions, 2017, 91(1): 15-25. DOI: 10.1080/01411594.2017.1350959.
[9] Becke A D. Density-functional thermochemistry. Ⅲ. The role of exact exchange [J]. The Journal of Chemical Physics, 1993, 98(7): 5648-5652. DOI: 10.1063/1.464913.
[10] Lu T, Chen F W. Quantitative analysis of molecular surface based on improved Marching Tetrahedra algorithm [J]. Journal of Molecular Graphics and Modelling, 2012, 38: 314-323. DOI: 10.1016/j.jmgm.2012.07.004.


Biographies: Cheng Jinjin(1991—), female, graduate; Ge Yuhua(corresponding author), male, doctor, professor, 101004698@seu.edu.cn.
Citation: Cheng Jinjin, Ge Yuhua.Synthesesand calculation of(E)-4-chloro-4’-ethoxystilbene and(E)-4, 4’-dichlorostilbene[J].Journal of Southeast University(English Edition), 2018, 34(3):408-41.DOI:10.3969/j.issn.1003-7985.2018.03.018.
Last Update: 2018-09-20