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Why are amidines more basic than amines?
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Keith Roman
Why are amidines more basic than amines?
Note that when you are comparing amidines with amines, you are comparing 2 nitrogen atoms with 1 unless you are comparing it with diamines. Amidines which have 2 ionizable nitrogen atoms are stabilized by 2 resonant structures, therefore making them more likely to accept protons (that is more basic). Similarly, guanidine (not to be confused with guanine which is a nucleic base) which has 3 ionizable nitrogen atoms are stabilized by 3 resonant structures thereby making it even more basic.
For additional reading, check out the basicity of the following drugs.
Betrixaban (which has 1 amidine group)
Pentamidine (which has 2 amidine groups)
Guanethidine (which has 1 guanidine group)
Metformin (a biguanide, that is, having 2 guanidine groups fused together)
Altretamine (which has 3 guanidine groups fused together into a cyclic structure)
Famotidine (which has 1 amidine group and 1 guanidine group).
Note that when you are comparing amidines with amines, you are comparing 2 nitrogen atoms with 1 unless you are comparing it with diamines. Amidines which have 2 ionizable nitrogen atoms are stabilized by 2 resonant structures, therefore making them more likely to accept protons (that is more basic). Similarly, guanidine (not to be confused with guanine which is a nucleic base) which has 3 ionizable nitrogen atoms are stabilized by 3 resonant structures thereby making it even more basic. For additional reading, check out the basicity of the following drugs.Betrixaban (which has 1 amidine group)Pentamidine (which has 2 amidine groups)Guanethidine (which has 1 guanidine group)Metformin (a biguanide, that is, having 2 guanidine groups fused together)Altretamine (which has 3 guanidine groups fused together into a cyclic structure)Famotidine (which has 1 amidine group and 1 guanidine group).
Note that when you are comparing amidines with amines, you are comparing 2 nitrogen atoms with 1 unless you are comparing it with diamines. Amidines which have 2 ionizable nitrogen atoms are stabilized by 2 resonant structures, therefore making them more likely to accept protons (that is more basic). Similarly, guanidine (not to be confused with guanine which is a nucleic base) which has 3 ionizable nitrogen atoms are stabilized by 3 resonant structures thereby making it even more basic. For additional reading, check out the basicity of the following drugs. Betrixaban (which has 1 amidine group) Pentamidine (which has 2 amidine groups) Guanethidine (which has 1 guanidine group) Metformin (a biguanide, that is, having 2 guanidine groups fused together) Altretamine (which has 3 guanidine groups fused together into a cyclic structure) Famotidine (which has 1 amidine group and 1 guanidine group).
Note that when you are comparing amidines with amines, you are comparing 2 nitrogen atoms with 1 unless you are comparing it with diamines. Amidines which have 2 ionizable nitrogen atoms are stabilized by 2 resonant structures, therefore making them more likely to accept protons (that is more basic). Similarly, guanidine (not to be confused with guanine which is a nucleic base) which has 3 ionizable nitrogen atoms are stabilized by 3 resonant structures thereby making it even more basic. For additional reading, check out the basicity of the following drugs.Betrixaban (which has 1 amidine group)Pentamidine (which has 2 amidine groups)Guanethidine (which has 1 guanidine group)Metformin (a biguanide, that is, having 2 guanidine groups fused together)Altretamine (which has 3 guanidine groups fused together into a cyclic structure)Famotidine (which has 1 amidine group and 1 guanidine group).
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