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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > September  >
In the Laboratory
Calix[4]pyrrole: Synthesis and Anion-Binding Properties. An Organic Chemistry Laboratory Experiment
James A. Shriver and Scott G. Westphal
Department of Chemistry, Central College, Pella, IA 50219
Cover
September 2006
Vol. 83 No. 9
p. 1330

Abstract
The study of synthetic macrocycles capable of interacting with small anionic species is an emerging field in organic chemistry. One specific example is a class of compounds known as calixpyrroles. The most common formulation of this system is a result of the condensation of acetone and pyrrole, which leads to the formation of a tetrapyrrolic macrocycle structurally similar but electronically different than porphyrins. This system is different from porphyrin in that you cannot form an 18π electron aromatic structure, which imparts drastically different properties. Instead, each pyrrole is electronically independent and consequently, each can donate one hydrogen bond. Their solid state structure also suggests that these meso-octamethylporphyrinogens are more aptly named calixpyrroles to emphasize their structural similarities to other members in the calixarene family. These observations led to the development of these systems as anion binding agents used to target a multitude of useful functions. Herein is described a three to four hour procedure introducing students to this system during their second term of organic chemistry. It has been optimized to have a completion time of three hours while allowing for optional characterization. The exploration of the anion-binding properties of calixpyrroles also makes this laboratory suitable for more advanced students.
Supplement
A detailed lab procedure for both parts of this experiment, a data sheet, and notes to the instructor are available.
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Citation
Shriver, James A.; Westphal, Scott G. J. Chem. Educ. 2006 83 1330.
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Keywords
Aromatic Compounds; Hands-On Learning / Manipulatives; Hydrogen Bonding; Laboratory Instruction; Molecular Recognition; Organic Chemistry; Second-Year Undergraduate; Synthesis; Thin Layer Chromatography; Upper-Division Undergraduate
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History
Created:
Last Updated:
8/7/2006
8/18/2006
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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