Nonplanar structures of thioamides derived from 7-azabicyclo [2.2. 1] heptane. Electronically tunable planarity of thioamides

…, M Kawahata, K Yamaguchi, T Ohwada

Index: Hori, Tetsuharu; Otani, Yuko; Kawahata, Masatoshi; Yamaguchi, Kentaro; Ohwada, Tomohiko Journal of Organic Chemistry, 2008 , vol. 73, # 22 p. 9102 - 9108

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Citation Number: 24

Abstract

X-ray crystallographic analysis showed that N-thiobenzoyl-7-azabicyclo [2.2. 1] heptane displays marked nonplanarity of the thioamide (1a, α= 167.1° and| τ|= 11.2°) as compared with the corresponding monocyclic pyrrolidine thioamide (2a, α= 174.7° and| τ|= 3.9°). In a series of para-substituted or unsubstituted thioaroyl-7-azabicyclo [2.2. 1] heptanes (1a− 1h), the planarity of the thioamide depended significantly on the electronic nature of the ...