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Cocrystal Controlled Solid-State Synthesis. A Green Chemistry Experiment for Undergraduate Organic Chemistry

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Miranda L. Cheney and Michael J. Zaworotko

Department of Chemistry, University of South Florida, Tampa, FL 33620

Steve Beaton and Robert D. Singer

Department of Chemistry, Saint Mary''s University, Halifax, Nova Scotia, Canada B3H 3C3

J. Chem. Educ., 2008, 85 (12), p 1649

DOI: 10.1021/ed085p1649

Publication Date (Web): December 1, 2008

Section:

History, Education, and Documentation

Abstract

Green chemistry has become an important area of concern for all chemists from practitioners in the pharmaceutical industry to professors and the students they teach and is now being incorporated into lectures of general and organic chemistry courses. However, there are relatively few green chemistry experiments that are easily incorporated into these undergraduate courses and clearly demonstrate the application of green chemistry principles. Experiments are described that can be adapted to a typical undergraduate organic chemistry course easily and are inexpensive, relatively safe, require no solvent (or extremely small quantities of solvent), have high atom economy, make use of non-toxic or low toxicity compounds, and generate negligible quantities of waste. The experiments can be accomplished through the use of a new technique known as cocrystal controlled solid-state synthesis, C³S³. The method not only represents an area of current high activity in the scientific research community but also exposes students to the actual practice and application of green chemistry.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

Green Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Amines / Ammonium Compounds

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Metal−Acetylacetonate Synthesis Experiments: Which Is Greener?
M. Gabriela T. C. Ribeiro and Adélio A. S. C. Machado
Journal of Chemical Education2011 Article ASAP
- Metal−Acetylacetonate Synthesis Experiments: Which Is Greener?
  M. Gabriela T. C. Ribeiro and Adélio A. S. C. Machado
  Journal of Chemical Education2011 Article ASAP
  A procedure for teaching green chemistry through laboratory experiments is presented in which students are challenged to use the 12 principles of green chemistry to review and modify synthesis protocols to improve greenness. A global metric, green star, ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Observation of Deuteration Effect in Co-Crystal System: Hexamethylenetetraminium 3,5-Dinitrobenzoate Hemideuterated Water
Li-Zhuang Chen, Hong Zhao, Jia-Zhen Ge, Ren-Gen Xiong and Hong-Wen Hu
Crystal Growth & Design2009 9 (9), 3828-3831
- Observation of Deuteration Effect in Co-Crystal System: Hexamethylenetetraminium 3,5-Dinitrobenzoate Hemideuterated Water
  Li-Zhuang Chen, Hong Zhao, Jia-Zhen Ge, Ren-Gen Xiong and Hong-Wen Hu
  Crystal Growth & Design2009 9 (9), 3828-3831
  Variable-temperature single-crystal X-ray diffraction, DSC (differential scanning calorimetry), and dielectric measurements show that the co-crystal system (D-HMTA)(DNBA)(0.5D2O) (1) (HMTA = hexamethylenetetramine, H-DNBA = 3,5-dinitrobenzoic acid) easily ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links