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1996
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October
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In the Classroom
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A Mnemonic for the Inositols
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Terence J. Painter
University of Trondheim, Norway
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October 1996
Vol. 73 No. 10
p. 949
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| Abstract |
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The mnemonic derives from the mythical tale of Scylla and Charybdis in Homer's Odyssey (chapter 12). It takes the form of an imaginary headline in a newspaper: SCYLLA MEETS CHARYBDIS - EPIC NEWS MUCH ALARMS SICILY. The first two or three letters in each of these eight words remind the user that the nine configurational prefixes are scyllo-, meso-, (or myo-), chiro- [(+) and (-)], epi-, neo-, muco-, allo-, and cis-, respectively. The mnemonic also arranges the prefixes in an order that allows the configurations to be derived in a logical manner by performing a defined sequence of imaginary configurational inversions (epimerizations) around a cyclohexane ring. The all-equatorial, chair conformation of scyllo-inositol is selected as the starting point, and the sequence of inversions is defined by a systematic permutation of possibilities for performing one, two or three inversions in succession (1; 1 and 2; 1 and 3; 1 and 4; 1, 2 and 3; 1, 2 and 4; and finally 1, 3 and 5). In the case of the two chiro-inositols, the enantiomeric form is determined simply by the direction (clockwise or counterclockwise) around the ring in which the imaginary inversions are performed. This also applies formally to allo-inositol, but in that case the two optical enantiomers are isoenergetic chair conformers in rapid equilibrium.
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| More Information |
 Citation |
Painter, Terence J. J. Chem. Educ. 1996 73 949.
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Keywords |
Organic Chemistry
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History |
Created:
Last Updated: |
September 22, 1999
February 21, 2006
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| Home > JCE Print > Journal of Chemical Education > Issues >
1996
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October
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949
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