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Which is more basic and why, cyclohexylamine or piperidine?
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Al Chou
Which is more basic and why, cyclohexylamine or piperidine?
I see there is some disagreement between the other authors of answers. One says cyclohexylamine, the other says piperidine. So, let’s look at the empirical data
So, piperidine is the stronger base (smaller the pKa, stronger the acid/weaker the base)
Why…well Mr. S. Jacks is correct…Secondary amines like piperidine are generally more basic than primary amines like cyclohexylamine. Carbon attached donates electron density to the Nitrogen better than Hydrogen.
And David Min is wrong. He confused piperidine with pyridine. However, Dr. Min is correct, pyridine (pKa = 5) is a weaker base.
I see there is some disagreement between the other authors of answers. One says cyclohexylamine, the other says piperidine. So, let’s look at the empirical data
So, piperidine is the stronger base (smaller the pKa, stronger the acid/weaker the base)
Why…well Mr. S. Jacks is correct…Secondary amines like piperidine are generally more basic than primary amines like cyclohexylamine. Carbon attached donates electron density to the Nitrogen better than Hydrogen.
And David Min is wrong. He confused piperidine with pyridine. However, Dr. Min is correct, pyridine (pKa = 5) is a weaker base.
Secondary amines like piperidine are generally more basic than primary amines like cyclohexylamine. Carbon attached donates electron density to the Nitrogen better than Hydrogen.
Secondary amines like piperidine are generally more basic than primary amines like cyclohexylamine. Carbon attached donates electron density to the Nitrogen better than Hydrogen.
I see there is some disagreement between the other authors of answers. One says cyclohexylamine, the other says piperidine. So, let’s look at the empirical data
pKa (cyclohexamuine) = 10.64
pKa (piperidine) = 11.28
So, piperidine is the stronger base (smaller the pKa, stronger the acid/weaker the base)
Why…well Mr. S. Jacks is correct…Secondary amines like piperidine are generally more basic than primary amines like cyclohexylamine. Carbon attached donates electron density to the Nitrogen better than Hydrogen.
And David Min is wrong. He confused piperidine with pyridine. However, Dr. Min is correct, pyridine (pKa = 5) is a weaker base.
I see there is some disagreement between the other authors of answers. One says cyclohexylamine, the other says piperidine. So, let’s look at the empirical data
pKa (cyclohexamuine) = 10.64
pKa (piperidine) = 11.28
So, piperidine is the stronger base (smaller the pKa, stronger the acid/weaker the base)
Why…well Mr. S. Jacks is correct…Secondary amines like piperidine are generally more basic than primary amines like cyclohexylamine. Carbon attached donates electron density to the Nitrogen better than Hydrogen.
And David Min is wrong. He confused piperidine with pyridine. However, Dr. Min is correct, pyridine (pKa = 5) is a weaker base.
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Secondary amines like piperidine are generally more basic than primary amines like cyclohexylamine. Carbon attached donates electron density to the Nitrogen better than Hydrogen.
Secondary amines like piperidine are generally more basic than primary amines like cyclohexylamine. Carbon attached donates electron density to the Nitrogen better than Hydrogen.
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