Concept

Hypervalency — where it appears

The apparent presence of more than eight electrons round a second-row atom. It needs no d orbitals: three-centre four-electron bonding puts twelve electrons round sulfur using only s and p, at the price of charge on the ligands.

Named by 17 essays across 2 fields — each of them below, with the objects they name alongside it.

sulfur hexafluoride — Oh. The molecule with the point group found from its coordinates rather than looked up: every candidate operation was applied and kept when it permuted the atoms among themselves.

Hypervalency without d orbitals

Sulfur hexafluoride is not d²sp³ hybridised. The d orbitals are far too high in energy to contribute meaningfully, the bonding is three-centre four-electron, and the textbook account has been known to be wrong for fifty years.

beyond · Hypervalency
Which rings close a shell. Each ring is filled with its own number of pi electrons and asked whether the highest occupied shell came out full. Of the rings drawn here, C6 and C10 close — at 6 and 10 electrons — which is Hückel's 4n+2, produced here rather than recalled.

Where two-centre bonding stops

A bond between two atoms is a special case, not the general one. Rings, clusters and metals are held together by orbitals spread over many centres, and the arithmetic that describes them is the arithmetic already used for benzene.

beyond · Multicentre
Hückel levels of three-centre four-electron. The orbital energies of the pi system, computed as the eigenvalues of the molecule's adjacency matrix. Degenerate levels share a line. The electrons are placed by aufbau with Hund's rule, so a half-filled degenerate shell shows as two unpaired spins.

Three-centre bonding, computed

Three orbitals in a line and four electrons: a bonding level, a level with exactly zero amplitude on the central atom, and an empty antibonding one. The middle atom never exceeds an octet, and the ligands carry the charge — which is why every molecule that needs this arrangement has electronegative ligands.

beyond · Hypervalency
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
Three orbitals in a line, four electrons in them. The three levels of a linear three-centre system, with the two lowest filled. The lower one is bonding across all three centres; the second has exactly zero amplitude on the middle atom, by symmetry rather than by arithmetic, so the two electrons in it sit entirely on the ends. That is where the charges come from: -0.5 on each end and +1 in the middle. Each of the two bonds has an order of 0.7071, which is 1/√2 and not the half the electron count suggests.

Hypervalency is about the ligands

The three-centre four-electron bond is offered as the reason sulfur hexafluoride needs no d orbitals. Read it forwards instead of backwards and it is a requirement rather than a permission — the arrangement puts half an electron onto each ligand before any electronegativity difference is applied, which is why the hypervalent compounds are fluorides and SH₆ is not a compound.

beyond · Hypervalency
Strong outside, weak inside. The bond orders along each chain. A three-centre system has two equal bonds of 0.707 — not the one half the electron count suggests — and every longer chain alternates, strong at the ends and weak in the middle. The spread grows with the chain: 3:0.000, 5:0.211, 7:0.271, 9:0.296. Nothing here is about iodine.

Hypervalency does not stop at three centres

The three-centre four-electron bond is written up everywhere as an arrangement peculiar to hypervalent molecules. It is the first member of a family — five centres and six electrons, seven and eight — and the family predicts alternating bond strengths that the polyiodide crystal structures have.

beyond · Hypervalency
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
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
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
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
One steps, the other slides — and the step is at the far end. The repulsion energy and the orphan count along the path from a tetrahedron to a square plane. The energy rises smoothly and monotonically, lowest at the tetrahedron and highest at the plane. The count is zero everywhere — including at 89.99° — and becomes one only at 90° exactly. The step is not near the energy's minimum; it is at its maximum, and it is at a single point.

A count that changes at one point

Where does the orphan count step along a distortion, relative to where the energy's minimum sits? A rule that depends on an exact symmetry may have no answer for a real molecule. On the path from a tetrahedron to a square plane the count is the same at every angle up to 89.99° and changes only at 90° exactly — which is the energy's maximum, not its minimum, and a single geometry out of a continuum.

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
Eighteen paths, two hundred and seventy geometries, one gap. Every one-parameter path between two arrangements of the same ligand count, each sampled at 15 geometries, with each geometry coloured by whether its group is named and tabulated, refused by the finder's tolerance, or a finite group with no table. The one gap is a group of order 10 at the pentagonal-pyramidal end of two paths — C5v, which no table here reaches. The path with a linear end is excluded, since a continuous group is declined deliberately rather than missing.

The gap found on purpose

A twist between two coordination arrangements passes through a point group with no character table among the twenty in use, and that was found by accident. Running every path between the arrangements — eighteen of them, two hundred and seventy geometries — finds exactly one more gap, at a group of order ten. It also finds something the search was not looking for: a group without a table had been reported as an infinite group.

beyond · Hypervalency
Folding the ring off its plane never gives the orbital back. For rings of four to eight ligands round a centre with no lone pair, the orphan count minus the formula n + L − 4, at polar angles from 60° to 120°. The upper dot in each row is the bare ring and the lower the same ring with a ligand on the axis. The bare ring is one over the formula at every angle, including 90°, where the ring is flat and its group is D₄ₕ, D₅ₕ or D₆ₕ; there is no table here for D₇ₕ or D₈ₕ. The capped ring agrees with the formula at every angle, 90° included, where the ring is exactly flat and the apex alone keeps its group C₄ᵥ to C₈ᵥ.

Folding the ring does not give the orbital back

Three arrangements break the orphan count n + L − 4, all flat, and the reason given was flatness: the p orbital perpendicular to the ring has no ligand combination of its species. Fold the ring into an umbrella at any angle and that orbital becomes totally symmetric — and the count stays wrong by exactly one, for rings of four to eight. The ring offers one symmetric combination to a centre with two symmetric orbitals. Writing C₅ᵥ to see it also counts the pentagonal pyramid at last, and the formula holds there.

beyond · Hypervalency

Named alongside it

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

Irreducible representationsPoint groupThree-centre bondingNon-bonding orbitalsReduction formulaElectron countModel limitSymmetry operationLone pairOctet ruleCharacter tableDegeneracy

All concepts