basicity

The Mesomeric Effect And Aromatic Amines

April 28, 2017

We’ve seen that several key factors influence the basicity of amines – charge, resonance, inductive effects, pi donor / pi acceptor behavior, hybridization and even the contribution of the nitrogen lone pa…

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5 Factors That Affect Basicity of Amines

5 Factors That Affect Basicity of Amines

April 26, 2017

What are the most important factors that affect the basicity of amines? Previously, we’ve seen how to evaluate the basicity of amines by examining the pKa of its conjugate acid (pKaH). (The higher the pKaH, th…

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Basicity of Amines And pKaH

Basicity of Amines And pKaH

April 18, 2017

How do you measure the basicity of an amine? Case in point: what’s a stronger base: pyridine or piperidine? Care to make a prediction? If you said piperidine, congratulations – it is indeed a stronger bas…

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Putting Acidity In Perspective

Putting Acidity In Perspective

January 25, 2013

[Source: xkcd  hat tip to Mike Evans @mevans86 for finding this] One concept that always seems to have a hard time getting through is that of pKa. No matter how many times I nag students to “know their pKasR…

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Leaving Groups Are Nucleophiles Acting In Reverse

Leaving Groups Are Nucleophiles Acting In Reverse

June 25, 2012

We’ve covered “what makes a good leaving group” before – the weaker the base, the better the leaving group. In this short post, I just want to make an observation. Note how similar nucleophiles…

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Nucleophilicity vs. Basicity

Nucleophilicity vs. Basicity

June 6, 2012

Following up on Nucleophiles and Electrophiles, here’s a common question students have about nucleophilicity: What’s the difference between nucleophicity and basicity? Great, great question. First of all, …

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Acid Base Reactions Are Fast

Acid Base Reactions Are Fast

May 21, 2012

Common dilemma in organic chemistry as you move through the latter parts of Org 1 and then into Org 2: When more than one reaction is possible, how do you know which one will happen? In a steel cage match between an a…

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Walkthrough of Acid-Base reactions (4) – pKa

Walkthrough of Acid-Base reactions (4) – pKa

May 9, 2012

So last time we went through all the different trends that affect acidity. The bottom line is that any factor which stabilizes the conjugate base will result in increased acidity.  Now it’s fine to know trends …

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Walkthrough of Acid-Base Reactions (3) – Acidity Trends

Walkthrough of Acid-Base Reactions (3) – Acidity Trends

April 25, 2012

Let’s review what’s been talked about so far in this series on acid-base reactions: An acid base reaction involves the donation of a proton (H+) from an acid to a base. The species which loses H+ is the ac…

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Walkthrough of Acid Base Reactions (2): Basicity

Walkthrough of Acid Base Reactions (2): Basicity

April 16, 2012

Last time I started writing about acid-base reactions. We looked at this list of stabilities of anions going across the topmost row of the periodic table.  Fluoride ion is the most stable in this series because it…

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