Crystal Structure of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4-diazaspiro[5.5]undecane -1,3,5,9-tetraone and its computational studies

Journal of Chemical Sciences

Hazem A Ghabbour4²  Assem Barakat1 2¹  Hoong-Kun Fun4²  Abdullah Mohammed Al-Majid¹  Saied M Soliman³  Mohammad Shahidul Islam¹ 

[1] Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia$$;Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia$$;Department of Chemistry, Rabigh College of Science and Art, King Abdulaziz University, P. O. Box 344, Rabigh 21911, Saudi Arabia$$

关键词: Spiro heterocycles;    [5+1] cyloaddition;    Michael Addition;    𝑁;    𝑁 -Dimethyl barbituric acid;    DFT-computation.;   

DOI  :  

来源: Indian Academy of Sciences

【 摘 要 】

Crystals of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4-diazaspiro[5.5]undecane -1,3,5,9-tetraone were grown in polar solvents and subjected to single crystal X-ray diffraction. The molecular crystal is Triclinic, P-1, 𝑎 = 8.3734 (19) Å, 𝑏 = 12.382 (3) Å, 𝑐 = 12.871 (3) Å, 𝛼 = 66.639 (7)° , 𝛽 = 85.148 (7)°, 𝛾 = 70.690 (6)° , 𝑉 = 1154.5 (5)Å3, 𝑍 = 2, Dcalc = 1.519 g cm−3. The optimized molecular structure of the studied compound using B3LYP/6-311G(d,p) method showed good agreement with the X-ray structure. The electronic and spectroscopic properties of the title compound were predicted. The NBO calculations were used to calculate the natural atomic charges at the different atomic sites as well as the intramolecular charge transfer (ICT) interactions among the most significant natural orbitals. The high LP(N)→ BD*(2)C-O ICT interaction energies indicate strong electron delocalization from the lone pair of the N-atoms of the pyrimidinetrione ring to the adjacent carbonyl groups. In contrast, the small LP(O)→ BD*(1)C-H stabilization energies (E(2)) indicated weak C-H—O interactions. Experimentally, the studied compound showed the most intense electronic transition band at 232 nm which is calculated using TD-DFT method as a shoulder at 231.3 nm (f=0.0832) and it belongs to H-3/H-1→L+1 and H-2→L+2 excitations. The GIAO calculated 1H and 13C NMR chemical shifts showed good correlations with the experimental data.

【 授权许可】

Unknown