Novel olefinic-centered macroacyclic compounds involving tetrasubstituted 4-hydroxybenzoic acid fragments: Synthesis, structural characterization and comparison of experimental and computational results


Er M., DEĞİRMENCİOĞLU İ. , TAHTACI H.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, cilt.139, ss.68-74, 2015 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 139
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.saa.2014.12.030
  • Dergi Adı: SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
  • Sayfa Sayıları: ss.68-74

Özet

Dialkyl 4,4'-(2-(1,3-bis(4-(alkoxycarbonyl)phenoxy)propan-2-ylidene)propane-1,3-diyl)bis (oxy)dibenzoate 6a,b were synthesized through the reaction of ethene-1,1,2,2,-tetra-yl-tetra methylene tetra bromide 1 with methyl 4-hydroxy benzoate or ethyl 4-hydroxy benzoate 2a,b. In addition, compounds 6a,b were obtained by using the esterification reaction from the reaction compound 5 with methyl and ethyl alcohol in high yields. Compound 4 was synthesized from the reaction of ethene-1,1,2,2,-tetra-yl-tetra methylene tetra bromide 1 with 4-hydroxy benzonitrile 3. The structures of the novel synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, COSY, elemental analysis, and mass spectral data. Compound 6b, C42H44O12, was also characterized with additional analysis such as UV-vis, and X-ray spectral techniques. The electronic structure of compound 6b was studied by DFT level 6-31G*(d,p) using X-ray crystallographic data. The results obtained from this study are consistent with the X-ray data. In order to understand the electronic transitions of the compound 6b, time dependent density functional theory (TD-DFT) calculations were carried out. TD-DFT studies showed that the low-energy excitations are consistent with the experimental results. (C) 2014 Elsevier B.V. All rights reserved.