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Article

Substituent Effects on the Basicity of 3,7-Diazabicyclo[3.3.1]nonanes

Supporting Info

Lauri Toom,^† Agnes Kütt,^‡ Ivari Kaljurand,^‡ Ivo Leito,^‡ Henrik Ottosson,^† Helena Grennberg,^† and Adolf Gogoll*^†

Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, SE-75123, Uppsala, Sweden, and Institute of Chemical Physics, University of Tartu, Jakobi 2, 51014, Tartu, Estonia

J. Org. Chem., 2006, 71 (19), pp 7155–7164

DOI: 10.1021/jo0604991

Publication Date (Web): August 22, 2006

†

Uppsala University.

‡

University of Tartu.

Corresponding author. Fax: +46-18-4713818. Tel: +46-18-4713822.

, Adolf.Gogoll@kemi.uu.se

Abstract

Basicity constants for a series of 3,7-diazabicyclo[3.3.1]nonane derivatives in acetonitrile with a variation over 13 orders of magnitude have been determined using a spectrophotometric titration technique. An excellent correlation between basicity and calculated proton affinities obtained at PCM-B3LYP/6-31+G(d)//B3LYP/6-31G(d) level was found. The results are discussed in terms of substituent effects and compared to ¹⁵N NMR chemical shifts.

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History

Published In Issue September 15, 2006
Received March 7, 2006

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Article

Substituent Effects on the Basicity of 3,7-Diazabicyclo[3.3.1]nonanes