How to Use the Solvent selection chart
Solvents known to swell polystyrene are shown in blue. Protic solvents are shown in red. Aprotic solvents are shown in black. N-methylformamide and N-methylacetamide are shown slightly lower than their t1 coordinates, 5.4 and 5.3, to compact the chart.
This chart is based on: “Screening of suitable solvents in organic synthesis. Strategies for solvent selection.” Carlson, R.; Lunstedt, T.; Albano, C. Acta Chem. Scand. B 1985, 39, 79-91. This work used principal components analysis of solvent properties [mp, bp, dielectric constant (e), dipole moment (m), refractive index (h), ET (spectroscopically determined effect on a solvatochromatic dye), and log P]. The eigenvectors were projected into two dimensions, t1 and t2, representing a conflation of properties that most differentiate these solvents, accounting for ?80% of their variance. Polarity correlates with t1, while polarizability correlates with t2. Solvents in the vicinity of one another in this chart should have similar properties. Solvents are positioned approximately to improve clarity.
For reactions with a known solvent dependence, select solvents in the vicinity of the known best solvent(s).For reactions with an unknown solvent dependence:
a. Select solvents that give uniform coverage of the solvent space (i.e., a regular lattice with a density consistent with the number of experiments desired). Both aprotic and protic solvents might be selected when compatible with reaction conditions.
b. Select solvents as dissimilar as possible. A D-optimal design selects solvents at the extreme periphery of the solvent space. A quadratic D-optimal design also includes a solvent near the origin.
c. Select typical solvents from each class (polar/non-polar, protic/aprotic, etc.).
From the Back Cover
A practical, hands-on guide that belongs in every organic chemistry lab
A unique reference that consolidates essential information in a practical, user-friendly format, The Synthetic Organic Chemist’s Companion provides a detailed description
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A thorough, accessible reference for organic chemists, laboratory technicians, or students, this guide merits a prominent place in every lab. It’s also a great textbook for upper-level undergraduate and graduate students studying organic chemistry, medicine, pharmaceuticals, and polymers.
About the Author
Michael C. Pirrung, PhD, is a Professor of Chemistry and UC Presidential Chair at the University of California-Riverside. He received his PhD in organic chemistry at UC-Berkeley in 1980 under the direction of Clayton Heathcock and did postdoctoral work with Gilbert Stork at Columbia as an NSF postdoctoral fellow. He is a member and is on the Steering Committee for the Chemical Genomics IGERT Program and has served on the Editorial Boards of the Journal of Combinatorial Chemistry, QSAR and Combinatorial Science, and Chemistry and Biology.
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