Several functional groups containing nitrogen are considerably stronger bases than are ordinary amines. One is the amidine

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Several functional groups containing nitrogen are considerably stronger bases than are ordinary amines. One is the amidine group found in DBN and DBU, both of which are widely used as bases in a variety of organic reactions. 

Amidine 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) group

Another unusually strong organic base is guanidine,

Indicate which nitrogen in each of these bases is the one most likely to be protonated and explain the enhanced strength of these bases relative to simple amines

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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