Organic chemistry Lewis theory

The more recent work finds its origin in the developments in theoretical organic chemistry which occurred after 1930. By means of the electronic theory of G. N. Lewis and by the consistent application of the ionic theory and that of equilibria to organic chemistry, C. K. Ingold and others began to classify the many compounds and reactions according to fundamental principles, a process which is well known to have yielded a rich harvest. 

Two acid-base theories are used in organic chemistry today the Br0nsted theory and the Lewis theory. These theories are quite compatible and are used for different purposes. ... 

In the Brpnsted picture, the acid is a proton donor, but in the Lewis picture the proton itself is the acid since it has a vacant orbital. A Brpnsted acid becomes, in the Lewis picture, the compound that gives up the actual acid. The advantage of Lewis theory is that it correlates the behavior of many more processes. For example, AICI3 and BF3 are Lewis acids because they have only 6 electrons in the outer shell and have room for 8. Both SnCU and SO3 have eight, but their central elements, not being in the first row of the periodic table, have room for 10 or 12. Other Lewis acids are simple cations, like Ag. The simple reaction A + B- A—B is not very common in organic chemistry, but the scope of the Lewis picture is much larger because reactions of the types... 

We wish to emphasise that the formation of esters (E) from alkenes (M) and acids (HA), the catalysis of the reactions of E by HA or MtXn, and the activation of E, such as organic chlorides, by the co-ordination of a Lewis acid, such as A1C13, are all very familiar chapters in conventional organic chemistry. It follows that the pseudo-cationic theory is nothing more than a generalisation of conventional organic-chemical ideas and a revival of some pre-Whitmore interpretations which had become occulted by the usefulness and novelty of the carbenium ion concept. 

Lowry praised the 1916 memoir of the American chemist Lewis as a "turning point in the history of chemistry" with its "plausible theory" of the electronic origin of the different types of chemical affinity and a clear differentiation between two kinds of valence, ionic and covalent. It is customary in mineral chemistry, he said, to consider reactions that occur between ions to be instantaneous, without attaching any importance to ionization in organic chemistry, except for the formation of salts from organic acids. 

It may have been the dramatic 1964 publication of E.S. Lewis and L. Funderburk that forced the question of hydrogen tunneling in complex solution reactions near room temperature into the consciousness of a larger scientific public, particularly in physical-organic chemistry. This article presented isotope effects for proton abstraction from 2-nitropropane by a series of substituted pyridines, and the values rose sharply as the degree of steric hindrance to the reaction increased (Fig. 1). AU the observed H/D isotope effects, from 9.6 to 24, were larger than expected from the simplest version of the so-called semiclassical theory of isotope effects (Fig. 2). 

Bykov s historical sketch of the electron theories of organic chemistry (1965) gives comprehensive coverage, with an emphasis on the application of quantum mechanics.426 R. E. Kohler has written on the origin of G. N. Lewis theory of the shared pair... 

Most chemists still tend to think about the structure and reactivity of atomic and molecular species in qualitative terms that are related to electron pairs and to unpaired electrons. Concepts utilizing these terms such as, for example, the Lewis theory of valence, have had and still have a considerable impact on many areas of chemistry. They are particularly useful when it is necessary to highlight the qualitative similarities between the structure and reactivity of molecules containing identical functional groups, or within a homologous series. Many organic chemistry textbooks continue to use full and half-arrows to indicate the supposed movement of electron pairs or single electrons in the description of reaction mechanisms. Such concepts are closely related to classical valence-bond (VB) theory which, however, is unable to compete with advanced molecular orbital (MO) approaches in the accurate calculation of the quantitative features of the potential surface associated with a chemical reaction. 

Electron donation-acceptance reactions, which are considered to be Lewis acid-base interactions, also include the formation of coordination compounds, complex formation through hydrogen bonding, charge transfer complex formation, and so on. It should be apparent that the Lewis theory of acids and bases encompasses a great deal of both inorganic and organic chemistry. 

The designation of electron-pair donors and acceptors as Lewis bases and Lewis acids is firmly and fittingly ingrained in the language of chemistry. G. N. Lewis laid the foundation for this important theory approximately 80 years ago and Lewis acids have since become increasingly important because of their central role in synthetic organic chemistry. This is clearly illustrated by an ever-increasing number of publications and books. 

March Advanced Organic Chemistry Reactions, Mechanisms, and Structure Memory Quantum Theory of Magnetic Resonance Parameters Pitzer and Brewer (Revision of Lewis and Randall) Thermodynamics Plowman Enzyme Kinetics... 

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