Al-Swaidan, Ibrahim A.;
El-Azab, Adel S.;
Alanazi, Amer M.;
Abdel-Aziz, Alaa A.-M.
Synthesis and Conformational Analysis of Sterically Congested (4R)-(−)-1-(2,4,6-Trimethylbenzenesulfonyl)-3-n-butyryl-4-tert-butyl-2-imidazolidinone: X-Ray Crystallography and Semiempirical Calculations
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Media type:
E-Article
Title:
Synthesis and Conformational Analysis of Sterically Congested (4R)-(−)-1-(2,4,6-Trimethylbenzenesulfonyl)-3-n-butyryl-4-tert-butyl-2-imidazolidinone: X-Ray Crystallography and Semiempirical Calculations
Contributor:
Al-Swaidan, Ibrahim A.;
El-Azab, Adel S.;
Alanazi, Amer M.;
Abdel-Aziz, Alaa A.-M.
Published:
Hindawi Limited, 2014
Published in:
Journal of Chemistry, 2014 (2014), Seite 1-15
Description:
The crystal structure of (4R)-(−)-1-(2,4,6-trimethylbenzenesulfonyl)-3-n-butyryl-4-tert-butyl-2-imidazolidinone(3)was determined by single-crystal X-ray diffraction. Compound3crystallizes in triclinic system in space groupP1 (≠1). The crystal data area=10.62165 Å,b=16.5321 Å,c=8.95729 Å,∝=91.1936∘,β=93.8496∘,γ=88.0974∘,V=1568.22 Å3,Z=3,Dcalc=1.253 g/cm3,μCuKα=15.98 cm−1,F000=636.00,T=20.0°C, andR=0.037. The crystal structure confirmed the occurrence of three molecules of3A,3B, and3Cin which then-butyryl moiety adopted thes-transoidconformation. Crystal structure also revealed that the conformation of 2,4,6-trimethylbenzenesulfonyl groups was inanti-position relative totert-butyl group. The crystal packing showed that three molecules of compound3are stacked as a result of intermolecularπ-πinteractions between the phenyl ring of one molecule and the phenyl ring of the other molecule by approaching each other to an interplanar separation of 5.034 Å. Interestingly, these stacked molecules are also connected by intermolecularCH-πinteraction. The conformational analysis of thes-transoid 3A,3B, and3Cwas separately performed by molecular mechanic MM+ force field. Additionally, computational investigation using semiempirical AM1 and PM3 methods was performed to find a correlation between experimental and calculated geometrical parameters. The data obtained suggest that the structural data furnished by the AM1 method is in better agreement with those experimentally determined for the above compound. It has been found that the lowest energetic conformer computed gives approximate correspondence with experimental solid state data.