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Structure and Bonding of Alkenes02:47

Structure and Bonding of Alkenes

Olefins, which are unsaturated hydrocarbons containing one or more carbon–carbon double bonds, are broadly divided into alkenes and cycloalkenes. The general chemical formula of an alkene is CnH2n.
Doubly bonded carbons are sp2 hybridized and have a trigonal planar geometry. The double bond is composed of a σ bond formed by the overlap of hybrid orbitals and a π bond produced by the lateral overlap of unhybridized 2p orbitals on both the carbons. Each carbon atom is bonded to two hydrogen atoms...
Structure of Alkanes02:23

Structure of Alkanes

The formation of carbon-carbon bonds leading to the creation of the carbon chain is the basis of organic chemistry. August Kekulé and Archibald Scott Couper independently developed this idea of carbon chain formation.
Hydrocarbons are the simplest organic compounds composed of carbons and hydrogens. Based on the bond order between carbons, the hydrocarbons are further classified into alkanes, alkenes, and alkynes. 
Alkanes are the simplest hydrocarbons with sp3 hybrid carbon atoms. These sp3...
Hydrogen Bonds01:04

Hydrogen Bonds

A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
Hydrogen Bonds00:26

Hydrogen Bonds

Hydrogen BondsHydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.Hydrogen Bonds Control the World!Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are...
Physical Properties of Alkanes02:33

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Alkanes are nonpolar molecules due to the presence of only carbon and hydrogen atoms. The electronegativity difference between carbon and hydrogen is minimal, and hence alkanes have a zero dipole moment. This leads to the presence of only dispersion forces between the molecules. The strength of dispersion forces is dependent on the surface area of the molecules on which they act. Since the surface area increases with the molecular length for straight-chain alkanes, the dispersion forces also...
Constitutional Isomers of Alkanes02:18

Constitutional Isomers of Alkanes

Organic compounds of the same molecular formula can have different structural formulas called constitutional isomers, and the phenomenon is known as constitutional isomerism. Alkanes with four or more carbons showing multiple structures with the same molecular formula thereby exhibit constitutional isomerism.
The linear isomer of an alkane is prefixed by the term “n”; hence a linear isomer of pentane is known as n-pentane. Based on the type of branching, some of the branched isomers are given...

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Hydrogen bonding to alkanes: computational evidence.

Solveig Gaarn Olesen1, Steen Hammerum

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This study reveals that hydrogen bonds significantly influence alkane and proton donor adducts. These interactions, similar to conventional hydrogen bonds, stabilize the adducts and alter vibrational properties.

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Area of Science:

  • Physical Chemistry
  • Computational Chemistry
  • Supramolecular Chemistry

Background:

  • Hydrogen bonding plays a crucial role in molecular interactions.
  • Understanding adducts of alkanes and proton donors is key to various chemical processes.

Purpose of the Study:

  • To investigate the structural, vibrational, and energetic properties of alkane-cationic proton donor adducts.
  • To elucidate the nature and strength of hydrogen bonding in these systems.

Main Methods:

  • Utilized composite ab initio calculations for theoretical analysis.
  • Employed Natural Bond Orbital (NBO) and Atoms in Molecules (AIM) analyses to substantiate findings.

Main Results:

  • Hydrogen bonding significantly contributes to the interaction energy in D-H(+)...H-alkyl adducts.
  • Observed characteristic hydrogen bond manifestations: D-H bond elongation, red shift in vibrational frequencies, and stabilization.
  • Alkane adducts show C-H bond elongation and red shifts due to charge-transfer interactions, weakening both O-H and C-H bonds.
  • Adducts exhibit bent structures with asymmetric bifurcated hydrogen bonds.
  • Hydrogen bond strength increases with isobutane and stronger acids.
  • Intramolecular hydrogen bonding in protonated alcohols behaves similarly to intermolecular interactions and can be equally strong.

Conclusions:

  • Hydrogen bonding is a dominant force in alkane-proton donor adducts, influencing their stability and properties.
  • The findings provide insights into the fundamental nature of non-covalent interactions in organic systems.