Inhaltszusammenfassung

Bond angles at thiohydroxamate oxygen in crystal structures of 3-alkoxy-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thiones gradually increased with the size of the 3-alkoxy substituent. This effect was attributed to strain on the basis of (i) a linear free energy relationship (Taft-Dubois correlation) and (H) signal coalescence from resonances of diastereotopic CH3 groups in solution (O-cumyl substituent; DNMR). Substitution at oxygen along the sequence OR (R prim-, sec-, and tert-alkyl), CH,...Bond angles at thiohydroxamate oxygen in crystal structures of 3-alkoxy-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thiones gradually increased with the size of the 3-alkoxy substituent. This effect was attributed to strain on the basis of (i) a linear free energy relationship (Taft-Dubois correlation) and (H) signal coalescence from resonances of diastereotopic CH3 groups in solution (O-cumyl substituent; DNMR). Substitution at oxygen along the sequence OR (R prim-, sec-, and tert-alkyl), CH, and OLi was reflected in a gradual decrease of N,O distances and lengthening of associated C,S bonds. The responsivity for these changes was more pronounced in the thiazole-2(3H)-thione than in the pyridine-2(1H)-thione series. (C) 2009 Elsevier Ltd. All rights reserved. » weiterlesen» einklappen

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