Concept

Reduction formula — where it appears

The expression giving how many times each irreducible representation appears in a reducible one. It divides by the group order, so it works only for a finite group and must return whole numbers or something is wrong.

Named by 27 essays across 6 fields — each of them below, with the objects they name alongside it.

A d shell in an octahedral field. The five d energies in octahedral coordination, computed and drawn in units of the octahedral splitting. The dashed line is the barycentre, which the five levels sum to whatever the arrangement.

The splitting is a symmetry statement

Put six ligands round a metal and the five d orbitals stop being degenerate. Which of them stay together, and how many sets there are, follows from the point group alone — before any account of what the ligands are made of, and before any number is computed.

applied · Ligand field
The Td character table. The irreducible representations of the molecule's point group. The class headings carry the number of operations found by generating the group from the coordinates, and those counts were produced before this table was opened.

Character tables and reduction

A molecule's point group is a list of matrices, not a label. Generating them, sorting them into classes, and dividing by the group order turns any set of orbitals into a statement about how many energies there can be.

symmetry · Representation
Eighteen electrons, from a reduction. The ligand σ orbitals of an octahedral complex reduced in Oh (A₁g ⊕ Eg ⊕ T₁u), matched against the metal's nine valence orbitals by species, and counted. 6 bonding and 3 non-bonding orbitals hold 18 electrons.

Eighteen is a count

The eighteen-electron rule is usually justified by adding up an s, three p and five d orbitals. That is a restatement rather than a reason. Reduce the ligand orbitals in the complex's own point group, match them against the metal's by symmetry, and the number that comes out is the count of orbitals lying below a gap — which is eighteen for an octahedron, sixteen for a square plane, and eighteen again for a tetrahedron for a different reason.

applied · Electron count
6 molecules, counted. How many vibrations each molecule has, how many symmetry species they fall into, and how many frequencies are infrared active, Raman active, both, or neither. Every column after the first counts frequencies rather than modes, because a degenerate pair is one line in a spectrum. The molecules with a centre of inversion are the ones with nothing in the both column — mutual exclusion as a computed count. Nothing here uses a force constant.

How many frequencies, not how many modes

Benzene has thirty vibrations. It has twenty distinct frequencies, and of those, eleven can be seen — four in the infrared and seven in the Raman, with no band in common. The other nine are invisible to both experiments, exactly.

spectra · Spectrum
The Td character table. The irreducible representations of the molecule's point group. The class headings carry the number of operations found by generating the group from the coordinates, and those counts were produced before this table was opened.

Degeneracy is a group theorem

How many orbitals can share an energy is decided before any energy is computed. The dimensions of a group's irreducible representations are the only degeneracies it permits, and a molecule with no representation larger than one cannot have a degenerate level at all.

symmetry · Representation
Oh descending to D4h. Every irreducible representation of Oh restricted to D4h and reduced there — A1g, A2g, Eg, T1g, T2g, A1u, A2u, Eu, T1u, T2u. A representation that arrives in more than one piece is a degeneracy the lower symmetry cannot hold, so a level carrying it must split when the molecule distorts.

Descent in symmetry

Lower a molecule's symmetry and its labels stop being available. Which of them survive, which split, and into what, is decided by restricting characters to the operations that are left — arithmetic, not a table to be looked up.

symmetry · Point group
carbon dioxide: D∞h worked in D2h. The vibrations of carbon dioxide, computed in D2h because D∞h has infinitely many operations and the reduction formula divides by the order of the group. Each constructed operation is checked against the molecule before use. The count must come out at 3N−5 rather than 3N−6 — 4 for 3 atoms — because rotation about the molecular axis moves no atom and is not a motion of the molecule at all.

An infinite group, worked in a finite one

A linear molecule has infinitely many symmetry operations, and every formula in character theory divides by the number of them. The standard device is to work in a finite subgroup — and it is worth computing what that trade costs rather than putting it in a footnote.

symmetry · Point group
F s on sulfur hexafluoride: a₁g ⊕ eg ⊕ t₁u. The character of the basis under each class of operations, which is a count of what did not move, and the multiplicities that come out of the reduction formula. The multiplicities must be whole numbers, and that is the check.

Six bonds and four orbitals

The six fluorine σ functions of sulfur hexafluoride span a₁g ⊕ eg ⊕ t₁u. Sulfur's 3s and 3p supply a₁g and t₁u and nothing else, so four bonding orbitals hold twelve electrons across six bonds — a bond order of two thirds, computed from characters with no energy anywhere in it.

symmetry · Hypervalency
methane: 2 valence bands. The measured valence photoelectron bands of methane, each labelled with the symmetry species of the orbital it comes from, and beside them the species the valence basis spans — the central atom's s and p functions and one s on each ligand, reduced in the molecule's own group. A band carrying a species the reduction does not produce would stop this figure being drawn.

What a photoelectron spectrum measures

The bands of a photoelectron spectrum are routinely read off as orbital energies. They are ionisation energies, which is a different quantity — and the identification rests on two errors of about an electronvolt each that happen to have opposite signs.

wrong · Photoelectron
Sixteen electrons, from a reduction. The ligand σ orbitals of a square planar complex reduced in D4h (A₁g ⊕ B₁g ⊕ Eu), matched against the metal's nine valence orbitals by species, and counted. 4 bonding and 4 non-bonding orbitals hold 16 electrons.

Sixteen is also a count

A transition metal brings nine valence orbitals, and nine filled orbitals is eighteen electrons. A square plane leaves more of those nine unmatched than an octahedron does and still holds fewer electrons, because one of the leftovers is out of reach.

applied · Electron count
water: 4 valence bands. The measured valence photoelectron bands of water, each labelled with the symmetry species of the orbital it comes from, and beside them the species the valence basis spans — the central atom's s and p functions and one s on each ligand, reduced in the molecule's own group. A band carrying a species the reduction does not produce would stop this figure being drawn.

Water's lone pairs are not a pair

Every course draws two equivalent lone pairs on water, pointing away from the hydrogens like a pair of ears. Its photoelectron spectrum shows the two bands they would produce at 12.6 and 14.7 electronvolts, two point one apart, in different symmetry species.

bonding · Photoelectron
Why a character table has the rows it has. All 20 groups this site defines, with the two counts that fix the shape of every character table: the number of representations equals the number of classes, and the sum of the squares of their dimensions equals the order of the group. Neither column pair differs anywhere in the table, and there is no room for another row in any of them.

Why a character table stops where it stops

A character table is square, and both of its dimensions are forced. The number of representations equals the number of classes, the squares of their dimensions sum to the order of the group, and between them there is no room for another row.

symmetry · Representation
ammonia: 3 valence bands. The measured valence photoelectron bands of ammonia, each labelled with the symmetry species of the orbital it comes from, and beside them the species the valence basis spans — the central atom's s and p functions and one s on each ligand, reduced in the molecule's own group. A band carrying a species the reduction does not produce would stop this figure being drawn.

Fewer bands than electrons

Methane has eight valence electrons and two photoelectron bands. Ammonia has eight and three; water has eight and four. The count is not of electrons, not of bonds and not of orbitals — it is of the symmetry species the occupied orbitals fall into, and it falls as the symmetry rises.

spectra · Photoelectron
Two answers from one projector: E1g. The E1g projection operator of benzene, applied to the pz function on one atom and then to the one on its neighbour. Both results belong to the same two-dimensional representation and span the same subspace; neither is more correct than the other; and they are different pictures, overlapping by 0.500. The circle areas are the coefficients and the two colours are their signs.

The projector is unique, the basis is not

A reduction says how many times each representation appears. It cannot say which combinations of orbitals they are — that takes a projection operator, and for a degenerate representation the operator returns a different pair of orbitals depending on which function it is handed first. Both pairs are correct, they span the same space, and every energy computed from either is identical.

symmetry · Representation
One distortion, resolved into the species of the group it left. An arbitrary displacement of benzene, projected onto each symmetry species of D6h. The weights add to 1, which is the check that the projectors resolve the whole of it: the largest is E2g at 35.0 per cent, and the totally symmetric part — 3.4 per cent here — is the part that changes every distance and no symmetry at all.

How far, and along which coordinate

A continuous symmetry measure returns one number: how far a structure is from a shape. Projecting the same displacement onto the twelve symmetry species of benzene's group turns it into a list that sums to 1.000000000000, says which coordinates the structure left along, and shows that the totally symmetric part — 3.4 per cent of this one — moves every atom by 0.0200 ångström and lowers the symmetry measure by nothing at all.

symmetry · Point group
Four, however many ligands there are. For each molecule, the number of ligand σ combinations that find a partner among the central atom's four s and p orbitals, against the number of ligands and lone pairs it has. The matched count rises along the diagonal and then stops at four, because there are four orbitals; everything above the ceiling is a pair with nowhere on the central atom to go, and that is what the word hypervalent names.

Four is all that s and p can match

Reduce the ligand σ set of ten molecules in each one's own point group and ask how many of its components transform as one of the central atom's four valence orbitals. The answer is never more than four — not by arrangement, in every geometry from linear to octahedral — and what is left over is n + L − 4, with exactly twice that many electrons in excess of an octet.

beyond · Hypervalency
The shallowest slope, and the steepest. For three molecules, the softest and stiffest vibrations, the species each belongs to, and what a unit distortion along each costs. The cost is not taken from the frequency: it is computed by resolving the distortion onto the normal coordinates in the mass-weighted metric and adding up ω²q². That it comes back as the frequency is the identity the whole comparison rests on — the species decomposition uses only the coordinates and the group, and the cost uses only the masses and the force constants, and the two have to agree on this case before they can be asked to disagree on any other.

The coordinate it was already soft along

A distorted structure can be resolved into the symmetry species of its ideal group, and that resolution cannot say which coordinate a molecule fell down by itself and which one something outside pushed it along. The force field answers that, and the two halves agree on the case where they must — a unit distortion along a normal mode costs exactly that mode's frequency, to a part in a million, computed from masses and force constants by one side and from coordinates and characters by the other.

symmetry · Point group
Where the orphan pair actually sits. A σ-only Hückel model of each molecule, built from its own coordinates: the central atom's four valence orbitals, one σ orbital on each ligand, and the coupling between them the direction cosine of that ligand. Lone pairs need no special handling — they come out of the diagonalisation as the central orbitals no ligand combination transforms like. The charge is measured rather than assigned, and PF₅ comes out with two kinds of fluorine at 3 at -0.13 and 2 at -0.3, the more charged pair being the axial one that carries the orphan.

The count is the population

The census counted how many ligand combinations have no partner on the central atom and called the count n + L − 4. A σ-only model built from each molecule's own coordinates says what that count is worth: with no electronegativity difference anywhere, the mean charge on a ligand is minus the orphan count divided by the ligand count, exactly, in all ten cases. And the prediction the census made — that the charge grows with the orphan count — is refused by the divisor.

beyond · Hypervalency
The even sharer is the one the repulsion likes least. trigonal bipyramid: 2 kinds of ligand, spread 0.1137, repulsion 6.4747; square pyramid: 2 kinds of ligand, spread 0.1658, repulsion 6.4844; pentagonal planar: 1 kind of ligand, spread 0.0000, repulsion 6.8819. The planar arrangement gives all five ligands exactly the same charge and costs 6.3 per cent more in repulsion than the bipyramid, which is the arrangement chemistry actually adopts — so the two models disagree about which arrangement is preferred, and about how much charge is moved.

Two models that disagree about the shape

The identity says how much charge a hypervalent molecule's ligands must share and nothing about how. Working out which arrangement shares it most evenly puts the σ model and the repulsion model on one axis for the first time: the even sharer is the pentagonal plane, which is the arrangement the repulsion likes least — and along the interchange chemistry actually uses, one model sees 0.15 per cent of a change and the other sees 54.

beyond · Hypervalency
A species label is ambiguous for every one of 17. For each molecule, the share of its vibrations belonging to a symmetry species that appears more than once — the distortions a species label cannot price, because the label picks a space rather than a mode. Every molecule in the census has at least one such species, the share averages 71.4 per cent, and for 9 of 17 the repetition is not forced by the group's capacity — those molecules have fewer vibrations than their group could hold without repeating, and repeat anyway.

A label that prices nothing

Pricing a distortion by its symmetry species works when the species appears once. It appears more than once for every one of seventeen molecules — 71.4 per cent of their vibrations on average belong to a species that is not unique — and for nine of the seventeen nothing forces it: their groups have room to spare and they repeat anyway.

symmetry · Point group
However hard the π channel is driven, the counted orbital stays the metal's. The metal's share of the filled T₂g orbital against the π coupling, with the eighteen-electron count drawn beside it. The share falls from 1 to 0.5467 across a coupling range of 80,000 cm⁻¹ and approaches a half from above without reaching it: the lower eigenvector of a two-level problem always carries more of the lower basis function, whatever the coupling. The count is eighteen at every point.

The count that cannot be broken by strength

Back-donation puts electrons into orbitals that are not the metal's, and the eighteen-electron rule counts the metal's nine. Turning the π channel up as far as it will go never breaks it: the counted orbital's metal share falls from 100 per cent to 54.67 and approaches a half from above without reaching it. What does flip it is not strength but order.

applied · Electron count
Ten molecules, twenty-six arrangements, three disagreements. Every arrangement of every one of the ten molecules, with the point group recovered from the arrangement's own coordinates and the ligand σ set reduced in it. 27 of them can be worked in a tabulated group; the formula n + L − 4 is right for 23 and wrong for 4. Every failure is a planar arrangement of four or more ligands, and every one of them is a molecule that does not adopt that arrangement.

The square that wastes an orbital

The orphan count that prices hypervalency was treated as a property of a molecule's composition — ligands plus lone pairs minus four. Run on twenty-six arrangements of the same ten molecules it is right for twenty-three and wrong for three, and all three are flat. A planar arrangement gives a main-group centre three usable orbitals rather than four, so the count is a property of the shape.

beyond · Hypervalency
Where the explanation gives a negative number of vibrations. The usual formula against the answer, for the 15 molecules with internal coordinates here. It is right for 7 of them and wrong for 8, and for sulfur hexafluoride, benzene and both ferrocenes it predicts a negative number of totally symmetric vibrations — which is the clearest possible sign that the quantity being subtracted is not the one that should be.

A formula that predicts minus eleven vibrations

A molecule's count of totally symmetric vibrations is often explained as one per orbit of internal coordinates, less one per redundancy, with methane as the worked example. Computed for fifteen molecules it is right for seven and wrong for eight — and for sulfur hexafluoride, benzene and both ferrocenes it returns a negative number. Two independent corrections turn it into an identity.

symmetry · Point group
The repulsion against the count, and they do not sort together. Every arrangement of the census by how many ligand σ combinations are left without a central partner and by how far its ligand repulsion sits above the best arrangement of that many points. The three that break the formula are marked. They are not the expensive ones: they sit at 4.2, 6.3, 9.8 per cent while the arrangements the formula gets right run to 26.5.

Expensive is not the same as unadopted

A counting formula right for twenty-three arrangements and wrong for three invites a reading: the failures are the arrangements nothing adopts, so the formula is reliable because chemistry stays away from where it breaks. Put the repulsion energy on the same axis and the reading fails — the most expensive arrangement in the census is one the formula gets right.

beyond · Hypervalency
The energy runs the whole way; the count exists at the two ends. The Coulomb repulsion of six ligands along the Bailar twist, from the trigonal prism at 0° to the octahedron at 60°, with the geometries that have an orphan count marked underneath. The energy is smooth and monotone, lowest at the octahedron. The count is defined at the two ends and at the handful of angles the symmetry finder rounds into them, and nowhere else — not because the geometry is unsymmetrical, but because its group is not tabulated.

The group nobody wrote a table for

The orphan count is predicted to be constant along the Bailar twist, because the twist keeps D3 the whole way. The premise is exactly right — at every angle strictly between the prism and the octahedron the symmetry finder assembles six operations that hold to four parts in 10¹⁶. The conclusion cannot be tested here, because a count is a reduction, and the calculation's nineteen character tables did not include D3.

beyond · Hypervalency
The same number, in three different groups, all the way along. The orphan count along the Bailar twist once the D3 character table is written. It is 2 at every one of the 15 geometries the symmetry finder answers for, across D3h at the prism, D3 through the whole interior and Oh at the octahedron. The lower row shows what the same sweep gave before the table existed: two ends and nothing between. This constancy was predicted from the premise that the twist keeps D3 throughout, and the premise was right.

The count the table was hiding

The interior of the Bailar twist looks uncountable — exactly D3 at every angle, and D3 is a point group whose character table is rarely written out. Writing it takes nine lines and settles the prediction made for the path: the orphan count is two at every geometry on the path that can be answered, in three different groups, out of three different decompositions.

beyond · Hypervalency
Two centres, one path, and the leftover changes sides. The count of leftover orbitals along the Bailar twist, for a main-group centre and for a transition metal. At four valence orbitals against six ligand combinations, two combinations are left with no partner and the count is a count of orphans; at nine against six, every combination finds one and three metal orbitals are left instead. Both are constant along the whole path, in three different point groups, out of decompositions that share no species — which is the replacement rule holding in a case where the arithmetic runs the other way.

The leftover changes sides

A main-group centre brings four valence orbitals against six ligand combinations, so two are orphaned. A transition metal brings nine, so the arithmetic inverts and three metal orbitals are left instead — three at every geometry of the Bailar twist, out of decompositions that share no species. Run past the whole arrangement census, exactly one arrangement orphans anything at a metal, and it needs an f orbital to fix.

beyond · Hypervalency

Named alongside it

The objects these essays reach for when they reach for this one.

Irreducible representationsPoint groupCharacter tableDegeneracySymmetry operationElectron countHypervalencyModel limitGroup orderNon-bonding orbitalsConventionLone pair

All concepts