Synthesis, Crystal Structure, DFT Studies and Hirshfeld Surface Analysis of N-(cyclohexyl(methyl)carbamothioyl)-4-nitrobenzamide

Abstract

In this study, new N-(cyclohexyl(methyl)carbamothioyl)-4-nitrobenzamide was synthesized in good yield and the compound was characterized by 1H NMR spectroscopic technique. In addition, the crystal structure of N-(cyclohexyl (methyl)carbamothioyl)-4-nitrobenzamide clarified by the X-ray single crystal diffraction technique. The compound crystallizes into monoclinic system with space group P21/c symmetry. The unit cell parameters of the crystal structure were determined as a = 14.858(4) Å, b = 5.0386(14) Å, c = 22.336(7) Å and β = 104.952(8)°. Density functional theory optimized structure in the gaseous phase at B3LYP/6-311G(d,p) level of theory has been compared with the experimentally defined molecular structure for N-(cyclohexyl(methyl)carbamothioyl)-4-nitrobenzamide compound. The HOMO and LUMO energies and energy gap were calculated for title compound. It was determined that there is an energy gap of 0.7772 eV between the HOMO and LUMO energy levels of the compound. This value indicated that the molecule had a high tendency to react chemically and was unstable. The graphical approach of the intermolecular interactions was obtained from the Hirshfeld surface analysis and 2D fingerprint plots was employed to quantifies various interaction. Hirshfeld surface analysis determined that the most dominant contribution to the surface area was due to H···H (42.10%) interactions.

Keywords

• DFT
• Synthesis
• Benzoylthiourea
• X-ray diffraction
• Hirshfeld surface
• Single crystal structure analysis

N-(Siklohekzil(metil)karbamotiyoil)-4-nitrobenzamit Bileşiğinin Sentezi, Kristal Yapısı, DFT Çalışmaları ve Hirshfeld Yüzey Analizi

Öz

Bu çalışmada, yeni N-(siklohekzil(metil)karbamotioil)-4-nitrobenzamit (1) bileşiği iyi verimle sentezlendi ve bileşik 1H NMR spektroskopik tekniğiyle karakterize edildi. Ayrıca, N-siklohekzil(metil)karbamotiyoil)-4-nitrobenzamit’in kristal yapısı, X-ışını tek kristal kırınım tekniği ile aydınlatıldı. Monoklinik sistemde kristallenen 1´in uzay grubu P21/c olarak tespit edildi. Kristal yapının birim hücre parametreleri a = 14,858(4) Å, b = 5,0386(14) Å, c = 22,336(7) Å ve β = 104,952(8)° olarak belirlendi. N-(Siklohekzil(metil)karbamotiyoil)-4-nitrobenzamit bileşiği için B3LYP/6-311G(d,p) teori seviyesinde gaz fazındaki yoğunluk fonksiyoneli teorisi ile optimize edilmiş yapı deneysel olarak tanımlanmış moleküler yapı ile karşılaştırıldı. 1 için HOMO ve LUMO enerjileri ve enerji boşluğu hesaplandı. Bileşiğin HOMO ve LUMO enerji seviyeleri arasında 0,7772 eV’luk bir enerji boşluğunun olduğu tespit edildi. Bu değer, molekülün kimyasal olarak reaksiyona girme eğiliminin yüksek olduğunu ve kararsız olduğunu gösterdi. Moleküller arası etkileşimlerin grafiksel yaklaşımı, Hirshfeld yüzey analizinden elde edildi ve çeşitli etkileşimleri ölçmek için 2D parmak izi çizimleri kullanıldı. Hirshfeld yüzey analizi, yüzey alanına en baskın katkının H···H (%42,10) etkileşimlerinden kaynaklandığı belirledi.

Anahtar Kelimeler

• DFT
• Sentez
• Benzoiltiyoüre
• X-ışını kırınımı
• Hirshfeld yüzey
• Tek kristal yapı analizi

Kaynakça

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