Amidine

Amidines are a class of oxoacid derivatives.

The oxoacid from which an amidine is derived must be of the form RnE(=O)OH, where R is a substituent. The −OH group is replaced by an −NH2 group and the =O group is replaced by =NR, giving amidines the general structure RnE(=NR)NR2 [1][2][3].

Contents

Carboxamidines

When the parent oxoacid is a carboxylic acid, the resulting amidine is a carboxamidine or carboximidamide (IUPAC name), and has the following general structure:

Carboxamidines are frequently referred to simply as amidines, as they are the most commonly encountered type of amidine in organic chemistry. The simplest amidine is formamidine, HC(=NH)NH2.

Examples of amidines include DBU and diminazene.

The most common way to make primary amidines is by the Pinner reaction.

Amidinate salts

An amidinate salt has the general structure M+[RNRCNR]- [4] and can be accessed by reaction of a carbodiimide with an organometallic compound such as methyl lithium. They are used widely as ligands in organometallic complexes.

See Also

References

  1. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "amidines".
  2. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "carboxamidines".
  3. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "sulfinamidines".
  4. ^ Chemistry and Technology of Carbodiimides Henri Ulrich