Hydrogen Bonding : from wikidavis and other sites with Chem 14c student commentary

In red or italics

Donors and Acceptors

In order for a hydrogen bond to occur there must be both a hydrogen donor and an acceptor present. The donor in a hydrogen bond is the atom to which the hydrogen atom participating in the hydrogen bond is covalently bonded, and is usually a strongly electronegative atom such as N,O, or F(rarely anything else) . The hydrogen acceptor is the neighboring electronegative ion or molecule, and must posses a lone electron pair in order to form a hydrogen bond.

Why does a hydrogen bond occur? Since the hydrogen donor is strongly electronegative, it pulls the covalently bonded electron pair closer to its nucleus, and away from the hydrogen atom. The hydrogen atom is then left with a partial positive charge, creating a dipole-dipole attraction between the hydrogen atom bonded to the donor, and the lone electron pair on the acceptor. ( also note that this doesn't have to be a dipole dipole interaction as noted on page 205 of the thinkbook, in this case F- is an ion and the CH3CH2OH molecules are dipoles so we have an ion dipole interaction ) This results in a hydrogen bond.

Types of hydrogen bonds

Hydrogen bonds can occur within one single molecule, between two like molecules, or between two unlike molecules. Intramolecular hydrogen bonds Intramolecular hydrogen bonds are those which occur within one single molecule. This occurs when two functional groups of a molecule can form hydrogen bonds with each other. In order for this to happen, both a hydrogen donor an acceptor must be present within one molecule, and they must be within close proximity of each other in the molecule. For example, intramolecular hydrogen bonding occurs in ethylene glycol (C2H4(OH)2) between its two hydroxyl groups due to the molecular geometry.

Intermolecular hydrogen bonds Intermolecular hydrogen bonds occur between separate molecules in a substance. They can occur between any number of like or unlike molecules as long as hydrogen donors and acceptors are present an in positions in which they can interact.For

example, intermolecular hydrogen bonds can occur between NH3 molecules alone, between H2O molecules alone, or between NH3 and H2O molecules.

http://chemwiki.ucdavis.edu/Physical_Chemistry/Quantum_Mec hanics/Intermolecular_Forces/Hydrogen_Bonding
http://www.bio.brandeis.edu/classes/biochem104/hydrogen_bonds.pdf This quoted from link above: , Quantum mechanical calculations show that the free electron pairs found on nitrogen and oxygen are delocalized around the hydrogen nucleus similar to the way electrons are shared by bonded atoms in a normal covalent bond.
What does this mean in relation to why do we require a lone pair of electrons. If we view hydrogen attached to the donor atom (N, O, F) as a naked H+ proton we can get an idea of why we need an electron pair on the acceptor atom. View the hydrogen bonding between the H delta + and the acceptor with the electrons delta as a bond that has covalent character. Seeing it this way, the lone pair is able to be delocalized around the hydrogen nucleus like completing its valence shell. Also this electron pair is needed to form the hydrogen bond without it be simply have a dipoledipole interaction For example in some bizarre world where oxygen had no lone pairs and only two bonds , while water might still be polar, it wouldnt have the 2 lone pairs . All electrons present would be participating in a bond and therefore no hydrogen bonding BUT! In our normal world the 2 lone pairs not participating in the covalent bond can participate as hydrogen acceptors,