RESONANCE
In a Chemistry resonance is
way of describing delocalized electrons within certain molecules or polyatomic ions where the bonding cannot be expressed by one single Lewis structure. A molecule or ion with such delocalized electrons is represented by several contributing structures.canonical structures, or, in older works or translations, mesomers), which collectively constitute a resonance hybrid.
DELOCALIZED ELECTRON
in resonance structures, the electrons are able to move to help stabilize the molecule. This movement of the electrons is called delocalization.
HISTORY OF RESONANCE
The concept first appeared in 1899 in Johannes Thiele's "Partial Valence Hypothesis" to explain the unusual stability of benzene which would not be expected from August Kekulé's structure proposed in 1865 with alternating single and double bonds.
The resonance proposal also helped explain the number of isomers of benzene derivatives. For example, Kekulé's structure would predict four dibromobenzene isomers, including two ortho isomers with the brominated carbons joined by either a single or a double bond. In reality there are only three dibromobenzene isomers and only one is ortho, in agreement with the idea that there is only type of carbon-carbon bond, intermediate between a single and a double bond.
The mechanism of resonance was introduced into quantum mechanics by Werner Heisenberg in 1926 in a discussion of the quantum states of the helium atom. He compared the structure of the helium atom with the classical system of resonating coupled harmonic oscillators.
In the classical system, the coupling produces two modes, one of which is lower in frequencythan either of the uncoupled vibrations; quantum mechanically, this lower frequency is interpreted as a lower energy. Linus Pauling used this mechanism to explain the partial valence of molecules in 1928, and developed it further in a series of papers in 1931-1933
The alternative term mesomerism popular in German and French publications with the same meaning was introduced by C. K. Ingold in 1938, but did not catch on in the English literature. The current concept of mesomeric effect has taken on a related but different meaning. The double headed arrow was introduced by the German chemist Fritz Arndt who preferred the German phrase zwischenstufe or intermediate stage.
In the Soviet Union, resonance theory – especially as developed by Pauling – was attacked in the early 1950s as being contrary to the Marxist principles of dialectical materialism, and in June 1951 the Soviet Academy of Sciences under the leadership of Alexander Nesmeyanov convened a conference on the chemical structure of organic compounds, attended by 400 physicists, chemists, and philosophers, where "the pseudo-scientific essence of the theory of resonance was exposed and unmasked".
In a Chemistry resonance is
way of describing delocalized electrons within certain molecules or polyatomic ions where the bonding cannot be expressed by one single Lewis structure. A molecule or ion with such delocalized electrons is represented by several contributing structures.canonical structures, or, in older works or translations, mesomers), which collectively constitute a resonance hybrid.
DELOCALIZED ELECTRON
in resonance structures, the electrons are able to move to help stabilize the molecule. This movement of the electrons is called delocalization.
HISTORY OF RESONANCE
The concept first appeared in 1899 in Johannes Thiele's "Partial Valence Hypothesis" to explain the unusual stability of benzene which would not be expected from August Kekulé's structure proposed in 1865 with alternating single and double bonds.
The resonance proposal also helped explain the number of isomers of benzene derivatives. For example, Kekulé's structure would predict four dibromobenzene isomers, including two ortho isomers with the brominated carbons joined by either a single or a double bond. In reality there are only three dibromobenzene isomers and only one is ortho, in agreement with the idea that there is only type of carbon-carbon bond, intermediate between a single and a double bond.
The mechanism of resonance was introduced into quantum mechanics by Werner Heisenberg in 1926 in a discussion of the quantum states of the helium atom. He compared the structure of the helium atom with the classical system of resonating coupled harmonic oscillators.
In the classical system, the coupling produces two modes, one of which is lower in frequencythan either of the uncoupled vibrations; quantum mechanically, this lower frequency is interpreted as a lower energy. Linus Pauling used this mechanism to explain the partial valence of molecules in 1928, and developed it further in a series of papers in 1931-1933
The alternative term mesomerism popular in German and French publications with the same meaning was introduced by C. K. Ingold in 1938, but did not catch on in the English literature. The current concept of mesomeric effect has taken on a related but different meaning. The double headed arrow was introduced by the German chemist Fritz Arndt who preferred the German phrase zwischenstufe or intermediate stage.
In the Soviet Union, resonance theory – especially as developed by Pauling – was attacked in the early 1950s as being contrary to the Marxist principles of dialectical materialism, and in June 1951 the Soviet Academy of Sciences under the leadership of Alexander Nesmeyanov convened a conference on the chemical structure of organic compounds, attended by 400 physicists, chemists, and philosophers, where "the pseudo-scientific essence of the theory of resonance was exposed and unmasked".
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