Experimental and theoretical investigation of molecular structure and conformation of the 4-isopropylthioxanthone

Autor(es)

Correa, Rodrigo S. ^{[1, 2]} ; Barolli, Joao P. ^[1] ; Ribeiro, Leandro ^[2] ; Batista, Alzir A. ^[1] ; Ellena, Javier ^[2] ; Andrade, Marcelo B. ^[2]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Carlos UFSCar, Dept Quim, BR-13561901 Sao Carlos, SP - Brazil

^[2] Univ Sao Paulo, Inst Fis Sao Carlos, Dept Fis & Informat, BR-13560970 Sao Carlos, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Molecular Structure; v. 1000, n. 1-3, p. 155-161, AUG 10 2011.
• Citações Web of Science: 4

Resumo

In this study, the molecular structure and conformational analyses of the 4-isopropylthioxanthone (4-ITX) are reported according to experimental and theoretical results. The compound crystallizes in the centrosymmetric P (1) over bar space group with only one molecule in the asymmetric unit, presenting the most stable conformation, in which the three fused-rings adopt a planar geometry, and the isopropyl group assumes a torsional angle with less sterical hindrance. The structural and conformational analyses were performed using theoretical calculations such as Hartree-Fock (HF), DFT method in combination with 6-311G(d,p) and 6-31++G(d,p) and the results were compared with infrared spectroscopy (FT-IR) and X-ray diffraction (XRD). The supramolecular assembly of 4-ITX is kept by non-classical C-H center dot center dot center dot O hydrogen bonds and weak interactions such as pi-pi stacking. 4-ITX was also studied by (1)H and (13)C NMR spectroscopy. UV-Vis absorption spectroscopic properties of the 4-ITX showed the long-wavelength maximum shifts towards high energy when the solvent polarity increases. (C) 2011 Elsevier B.V. All rights reserved. (AU)

• Processo FAPESP: 09/08131-1 - Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas citotoxicidades em células tumorais
• Beneficiário: Rodrigo de Souza Corrêa
• Modalidade de apoio: Bolsas no Brasil - Doutorado