Abstract
A fundamental and ubiquitous phenomenon in chemistry is the contraction of both C−H and C−C bonds as the carbon atoms involved vary, in s–p hybridization, along sp3 to sp2 to sp. Our quantum chemical bonding analyses based on Kohn–Sham molecular orbital theory show that the generally accepted rationale behind this trend is incorrect. Inspection of the molecular orbitals and their corresponding orbital overlaps reveals that the above‐mentioned shortening in C−H and C−C bonds is not determined by an increasing amount of s‐character at the carbon atom in these bonds. Instead, we establish that this structural trend is caused by a diminishing steric (Pauli) repulsion between substituents around the pertinent carbon atom, as the coordination number decreases along sp3 to sp2 to sp.
Highlights
A fundamental and ubiquitous phenomenon in chemistry is the contraction of both CÀH and CÀC bonds as the carbon atoms involved vary, in s–p hybridization, along sp3 to sp2 to sp
The geometrical properties of organic molecules are, in general, explained using hybridization theory, which was introduced by Linus Pauling in 1931.[1,2] A case in point is the fundamental and ubiquitous phenomenon in chemistry that CÀH and CÀC bonds contract as the carbon atoms involved vary, in s–p hybridization, along sp3 to sp2 to sp
We find that a diminishing steric (Pauli) repulsion between substituents around the carbon atom constitutes the physical mechanism behind the universal trend in molecular structure, as the number of substituents around the pertinent carbon atom decreases from 4 to 3 to 2 along sp3 to sp2 to sp hybridization, respectively
Summary
The following full text is a publisher's version. For additional information about this publication click this link. https://repository.ubn.ru.nl/handle/2066/236451.
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