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Crystal Structure of 2, 8, 14, 20-tert-Butylpyrogallol[4]arene

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Abstract

The aromatic derivative 2, 8, 14, 20-tert-butylpyrogallol[4]arene was synthesized by the acid catalyzed condensation of pivalaldehyde and pyrogallol in refluxing aqueous ethanol. Single crystal X-ray analysis revealed that the molecule crystallizes in the monoclinic crystal system; space group: P21/c. Unit cell dimensions: a = 11.1175(7) Å, α = 90°, b = 23.4525(15) Å, β = 101.6720(10)°, c = 21.9595(14) Å, γ = 90°, Dcalc = 1.205 Mg/m3 g/m3 for Z = 4. In the solid state, the macrocycle is found to adopt a crown structure that is unique for the rcct conformation.

Graphical abstract

Crystal Structure of 2, 8, 14, 20- tert -Butylpyrogallol[4]arene

Eric E. Dueno, Allen D. Hunter, Matthias Zeller, Thomas A. Ray, Ralph N. Salvatore, Cesar H. Zambrano

Acid catalyzed condensation of pyrogallol and pivalaldehyde in refluxing aqueous ethanol afforded a pyrogallol[4]arene derivative in good yield. Single crystal X-ray diffraction analysis revealed that a new calyx-like structure was formed under the reaction conditions.

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Notes

  1. The volume of the crown structure was calculated with the formula: \( {{\rm V}} = (1/3)h\pi ({{\rm R}}_{{1}}^{{2}} + {{\rm R}}_{{1}}{{\rm R}}_{{2}}+ {{\rm R}}_{{2}}^{{2}}) \), where h is the average height of the cone and R1 and R2 are the average radius of the lower rim and upper rim, respectively

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Acknowledgements

EED acknowledges the National Science Foundation for primary support of this research (EPSCOR Grant No. 450901). MZ acknowledges NSF grant 0087210, the Ohio Board of Regents grant CAP-491, and YSU for funding the diffractometer. CZ is thankful to Andrea Alejandra Saltos R. (USFQ), who helped with the computational work.

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Authors and Affiliations

  1. Department of Chemistry, Eastern Kentucky University, 521 Lancaster Ave., Richmond, KY, 40475, USA

    Eric E. Dueno & Thomas A. Ray

  2. Department of Chemistry, Youngstown University, 1 University Plaza, Youngstown, OH, 44555-3663, USA

    Allen D. Hunter & Matthias Zeller

  3. Lehman College, City University of New York, Davis Hall 317, 250 Bedford Park Boulevard, West Bronx, New York, 10468, USA

    Ralph N. Salvatore

  4. Departamento de Quimica, Universidad San Francisco de Quito, Pampite & Robles - Cumbayá, Quito, Ecuador

    Cesar H. Zambrano

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  1. Eric E. Dueno
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Correspondence to Cesar H. Zambrano.

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Dueno, E.E., Hunter, A.D., Zeller, M. et al. Crystal Structure of 2, 8, 14, 20-tert-Butylpyrogallol[4]arene. J Chem Crystallogr 38, 181–187 (2008). https://doi.org/10.1007/s10870-007-9285-7

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