Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur

Problem 1.13 Draw a line-bond structure for propyne. Cl IjC=CH indicate the hybridization of 

The valence-bond concept of orbital hybridization described in the previous lour sections is not limited to carbon compounds. Covalent bonds formed by other elements can also be described using hybrid orbitals. Look, for instance, at the nitrogen atom in tnethylaniine, CH3Nli2 an organic derivative of ammonia (XH d and the substance responsible for the odor of rotting fish. 

Like the carbon atom in methane and the nitrogen atom in methydamine, tlie oxygen atom in methanol (methyl alcohol) and many other organic molecules can also be described as sp -hybridized. The C—O—H bond angle in methanol is 108.5°, verv dose to the 109.5° tetrahedral angle. Two of the four sp- hybrid 

Phosphorus and sulfur are the third-row analogs of nitrogen and oxygen, and the bonding in both can be described using hybrid orbitals. Because of their positions in the third row, however, both phosphorus and sulfur can expand their outer-shell octets and form more than the typical number of covalent bonds. Phosphorus, for instance, often forms five covalent bonds, and sulfur occasionally forms four. 

Thomson Click Organic Interactive to learn howto identify hybridization in a variety of organic molecules. 

The experimentally measured H-N-H bond angle in methylamine is 107.1° and the C-N-H bond angle is 110.3°, both of which are close to the 109.5° tetrahedral angle found in methane. We therefore assume that nitrogen hybridizes to form four sp orbitals, just as carbon does. One of the four orbitals 

---

Atomic Structure The Nucleus Atomic Structure Orbitals 4 Atomic Structure Electron Configurations 6 Development of Chemical Bonding Theory 7 The Nature of Chemical Bonds Valence Bond Theory sp Hybrid Orbitals and the Structure of Methane 12 sp Hybrid Orbitals and the Structure of Ethane 13 sp2 Hybrid Orbitals and the Structure of Ethylene 14 sp Hybrid Orbitals and the Structure of Acetylene 17 Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur 18 The Nature of Chemical Bonds Molecular Orbital Theory 20 Drawing Chemical Structures 21 Summary 24... 

As a general trend, the interest in the chemistry of hybrid phosphorus-oxygen, nitrogen or/and sulfur donor ligands is mainly focused on the phenomenon of their hemilability and their potential use in catalytic processes. Other possibilities are found when these P,X (O, N, S) donors are integrated in macrocyclic systems, such as the documented ability of their derivatives to interact selectively with ionic species... 

---