Abstract
The text-book Walden cycle which interconverts the stereochemical configurations of chlorosuccinic and malic acids involves a beta-lactone intermediate in preference to an alpha-lactone intermediate because the O-nuc C Cl angle in the transition structure for the former (174 degrees) is more favourable than that for the latter (139 degrees), as determined by PCM(epsilon = 78.4)/B3LYP/6-31+G* calculations; the smaller ring-strain energy of the beta-lactone contributes little to the reactivity difference.
Original language | English |
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Pages (from-to) | 1106-1108 |
Number of pages | 3 |
Journal | Chemical Communications |
Issue number | 10 |
DOIs | |
Publication status | Published - 2006 |