Formal Charges, Reactivity, Acids (electrophiles) & Bases (nucleophiles)

 

 

The following table summarizes the formal charge on a central atom, and the reactivity of several of the most important species in organic chemistry.  

 

Species

Lewis Structure

Valence Electrons "Owned" by Central Atom

Valence Electron Count of Neutral Central Atom

Formal Charge of Central Atom 

Reactivity

neutral

+

 

4

4

0

very low

carbocation

3

4

+1

high: strong electron pair acceptor
(ACID)

free radical

-

 

4

4

0

high: (due to unpaired electron)

anion

5

4

-1

high: strong electron pair donor
(BASE)

ammonia

5

5

0

weak electron pair donor; weak electron pair acceptor
(BASE)

ammonium ion

(cation)

-

 

+

 

4

5

+1

strong electron pair acceptor
(ACID)

amide ion

(anion)

6

5

-1

high: strong electron pair donor
(BASE)

Water

(neutral)

6

6

0

weak electron pair donor; weak electron pair acceptor
(ACID or BASE)

hydronium ion

(cation)

-

 

+

 

5

6

+1

strong electron pair acceptor
(ACID)

hydroxide ion

(anion)

7

6

-1

strong electron pair donor
(BASE)

bonded hydrogen

(neutral)

1

1

0

low unless activated by  neighboring atom(s)

hydride

(anion)

-

 

2

1

-1

strong electron pair donor
(BASE)

proton

(cation)

+

 

0

1

+1

strong electron pair acceptor
(ACID)

hydrogen

atom (free radical)

1

1

0

high: (due to unpaired electron)