An evaluation of amide group planarity in 7-azabicyclo [2.2. 1] heptane amides. Low amide bond rotation barrier in solution

…, K Yamaguchi, G Yamamoto, M Uchiyama…

Index: Otani, Yuko; Nagae, Osamu; Naruse, Yuji; Inagaki, Satoshi; Ohno, Masashi; Yamaguchi, Kentaro; Yamamoto, Gaku; Uchiyama, Masanobu; Ohwada, Tomohiko Journal of the American Chemical Society, 2003 , vol. 125, # 49 p. 15191 - 15199

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Citation Number: 78

Abstract

Here we show that amides of bicyclic 7-azabicyclo [2.2. 1] heptane are intrinsically nitrogen- pyramidal. Single-crystal X-ray diffraction structures of some relevant bicyclic amides, including the prototype N-benzoyl-7-azabicyclo [2.2. 1] heptane, exhibited nitrogen- pyramidalization in the solid state. We evaluated the rotational barriers about the amide bonds of various N-benzoyl-7-azabicyclo [2.2. 1] heptanes in solution. The observed ...