Concept

Point group — where it appears

The set of symmetry operations that leave a molecule looking unchanged, closed under multiplication. It decides polarity, chirality and every selection rule, and assigning one to a real structure requires a tolerance somebody chose.

Named by 49 essays across 5 fields — each of them below, with the objects they name alongside it.

ammonia — C3v. 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.

Point groups from coordinates

A molecule's symmetry is not a label to be looked up. It is decidable from the atom positions by searching for the operations that permute them, and the search either finds an operation or it does not.

symmetry · Point group
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
Five sites are not five of a kind. The minimised arrangement of five points, with the two axial sites marked apart from the three equatorial ones. Their neighbour angles differ, so the two kinds of position are genuinely different places — which the shape's name does not convey.

Five sites are not alike

Every other common arrangement has one or two distinct angles. Five has three, because two of its positions are on an axis and three are round an equator — and a molecule built that way does something about it.

shape · VSEPR
What the group settles. For each molecule, the point group found from its coordinates and the two properties that follow from the group alone. Neither column required knowing anything about the bonds.

Symmetry forbids a dipole

Whether a molecule can have a dipole moment follows from its point group alone. The usual argument — adding up bond vectors — gets the right answer for easy cases by a route that does not generalise.

symmetry · Point group
bromochlorofluoromethane — C1. 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.

Chirality is a symmetry statement

A molecule is chiral when its group contains no improper operation at all. The four-different-groups rule is a useful special case that misses molecules with no stereocentre and wrongly condemns some that have several.

symmetry · Point group
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
4 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.

Two structures, two spectra

A linear XY₂ gives two infrared bands, one Raman band and no band in common. A bent XY₂ gives three of each and three in common. Counting settles the shape, without a force constant, an assignment or a single measured frequency.

spectra · Spectrum
phosphorus pentafluoride — D3h. 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.

Site symmetry, and what it constrains

A molecule's group is not the only group in the problem. Each atom sits at a position with a symmetry of its own, and what that local group permits decides how many kinds of environment a structure really has.

symmetry · Representation
phosphorus pentafluoride: 3 environments. The atoms of phosphorus pentafluoride sorted into orbits under its own symmetry group — two atoms are in the same orbit when an operation of the group carries one onto the other, which makes them indistinguishable by any measurement. There are 2 of F, 1 of P, and a spectrum that resolves environments counts those rather than atoms.

A spectrum counts environments, not atoms

Phosphorus pentafluoride has five fluorines in two inequivalent sets, so its magnetic resonance spectrum should show two signals. It shows one — and the reason is not a symmetry the molecule has but a motion faster than the measurement.

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
Angles at exponents 1, 2, 3, 6, 12. The distinct angles of the minimised arrangement of 4, 5, 6, 7 points, under a repulsion going as one over r to the power 1, 2, 3, 6, 12. Where the arrangement is the maximally symmetric one the angles do not move at all; where it is not, both the angles and how many of them there are depend on the law assumed.

Which angles are symmetry and which are the model

VSEPR says electron pairs repel and never says by what law. For four, five and six domains it makes no difference whatever — change the exponent by a factor of twelve and not one angle moves. For seven it decides the answer.

shape · VSEPR
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
carbonyl sulfide: a linear. The principal axes of carbonyl sulfide drawn at its centre of mass, with the moment of inertia about each. Which kind of top this makes it is decided by comparing three numbers, and the point group forces the same answer independently: an axis of order infinity means a linear molecule, with one moment at zero forbids an asymmetric top.

The rotational spectrum is a moment of inertia

Every line in a microwave spectrum sits at a multiple of one number, and that number is a conversion constant divided by a sum of mass times distance squared. No bonding argument appears anywhere in it.

spectra · Rotation
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
One dihedral, three point groups. Hydrogen peroxide built at 13 values of its dihedral angle, with the point group searched for from the coordinates at each. The group is C2v when the hydrogens eclipse, C2h when they are anti, and C2 at every angle strictly between. The rails below are what the group settles on its own: the molecule may be polar except at the anti arrangement, and it is chiral except at the two ends. No energy is computed anywhere, and the marked angle is the measured one rather than a minimum found here.

One coordinate, three point groups

Hydrogen peroxide has four atoms and one soft internal coordinate. Turning it from nought to a hundred and eighty degrees takes the molecule through C2v, C2 and C2h — so it is chiral at every angle but two, and forbidden a dipole at exactly one of them.

shape · Dipole
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
The moment that does not depend on where the origin is. For each molecule, the dipole and the largest quadrupole component about the centre, and the same two about an origin moved 1.6 bohr away. The lowest non-vanishing moment is unchanged in every row and the one above it moves in every row. The 4 non-polar molecules here have a quadrupole that is a property of the molecule; the polar ones have one that is a property of a choice.

What a dipole cannot tell apart

A dipole moment is three numbers extracted from a whole charge distribution, and enormously many distributions give the same three. The moment above it is not even a property of the molecule unless the one below it vanishes — which is why a quadrupole is quoted with an origin and a dipole is not.

shape · Dipole
Dipole selection rules in Oh. For every pair of symmetry species, whether an electric dipole transition between them is allowed and along which polarisation. An entry is allowed exactly when the triple product of representations contains the totally symmetric one.

Why a d–d band is weak

In a centrosymmetric complex the transition between the two halves of a split d shell is forbidden — exactly, by parity, with no small quantity anywhere. What makes it visible at all is that the molecule is never quite centrosymmetric, and the computation says which vibrations do the work.

spectra · Representation
methane, substituted 5 ways. CH₄, CH₃D, CH₂D₂, CHD₃, CD₄ — the same molecule with the same force constants, differing only in which nuclei are heavy. Every column is a consequence of which of the parent's operations survive the mass pattern: the surviving set is a subgroup, it is named from its own conjugacy classes, and the vibrations are reduced in it. The allowed and computed columns come from group theory and from the mass-weighted Hessian respectively, and they agree in every row.

A spectrum that changes when only a mass does

Methane has four distinct vibrational frequencies and two infrared bands. Replace two of its hydrogens with deuterium and it has nine and eight — with every force constant identical, every nucleus where it was, and the potential energy surface unchanged.

spectra · Spectrum
How many groups a molecule can fall to. For each molecule, every subgroup of its point group, found by closing subsets of the operations recovered from its atom positions — beside the number the corresponding abstract group is known to have. The two agree in all 4 cases. The last column is how many of those subgroups this site holds a character table for, which is a minority in every row but the first.

Every group a molecule can fall to

A distortion takes a molecule's symmetry away, and what is left is not a free choice — it has to be a group. Closing subsets of methane's twenty-four operations returns thirty of them, which is exactly the number the symmetric group on four letters has.

symmetry · Point group
7 molecules, three moments each. The principal moments of inertia of water, sulfur dioxide, formaldehyde, boron trifluoride, ammonia, methane, hydrogen peroxide, in u Ų, with the inertial defect and the asymmetry parameter beside them. The defect vanishes exactly for a planar structure and does not for any other, so three numbers computed from the coordinates decide planarity with no model anywhere in the argument. Every classification is checked against the one the molecule's point group forces.

The moment that is the sum of the other two

Three numbers computed from the coordinates and the masses decide whether a molecule is flat. For water, sulfur dioxide, formaldehyde, benzene and every other planar structure here the largest moment of inertia is the sum of the other two exactly; for ammonia it misses by 0.76 and for methane by 3.18.

spectra · Rotation
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
The group of benzene, against how much error is forgiven. Four distortions of benzene, none larger than six hundredths of an ångström, and the point group the search reports for each at nine tolerances. The exact structure is D6h at every one of them, so the staircases below belong to the distortions rather than to the search. The cell marked in warning colour is a step at which the order of the group named at the tighter tolerance does not divide the order of the one named at the looser: C6h of order 12, so the sequence is not a chain of subgroups.

The tolerance is a decision

A measured structure is never exactly symmetric, so assigning it a point group means deciding how much error to forgive. Sweep that decision from a thousandth of an ångström to a third of one and benzene, bent by a hundredth, is assigned five different groups — and at one step the group named is not even a supergroup of the one named before it.

symmetry · Point group
Mutual exclusion across every group here. The 20 groups with tables here, each with its highest rotation order, whether it has a centre of inversion, which of its representations carry a coordinate, which carry a product of coordinates, and whether any carries both. Every group with a centre excludes, which is a theorem. 1 group without a centre excludes as well — D5h — so the rule does not run backwards, and the counterexample needs a fivefold axis.

Mutual exclusion does not prove a centre

A centrosymmetric molecule shows no band in both its infrared and its Raman spectrum. The rule is a theorem and its converse is read off as though it were part of it — but ferrocene in the gas phase has no centre of inversion and no coincidence either, and the reason is that a fivefold axis separates the coordinates from their products where a threefold or fourfold axis cannot.

spectra · Spectrum
Three counts for each molecule, and the barrier between them. Four molecules, with the number of operations available to each: the point group, which is what a rigid rotation or reflection can do; the feasible group, which adds whatever a crossable barrier makes available; and the whole permutation-inversion group, which is every rearrangement of identical nuclei whether a molecule can reach it or not. The middle column is the one that describes a real spectrum, and it equals the first only when nothing moves.

The group of a molecule that will not hold still

A point group is a group of rotations of space, and it presupposes a structure for them to act on. Ethane has no one structure — its methyl groups turn billions of times a second — and the group that describes its spectrum has thirty-six elements where the point group has twelve, out of two thousand eight hundred and eighty conceivable.

symmetry · Point group
Every set of point groups here that shares a table. Found by comparing character matrices rather than named: five sets among the tabulated groups, at orders 2, 4, 6, 8, 20. The smallest is the most startling — a mirror plane, a centre of inversion and a twofold axis all have the two-row table with entries 1, 1 and 1, −1, and one of the three describes a chiral molecule. The largest is the eclipsed and staggered conformers of ferrocene, which are one molecule at two temperatures.

One table, three groups

A mirror plane, a centre of inversion and a twofold axis have the same character table — two rows, entries 1, 1 and 1, −1 — and one of the three describes a chiral molecule. A character table is a property of an abstract group; a point group is that plus an action on space, and the action is what a molecule has.

symmetry · Representation
Face to face repels, edge to face attracts. Two benzene molecules 5 Å apart, one turned against the other, with only the quadrupole interaction between them. Stacked, the two negative faces meet and the energy is +8.8 kJ/mol; perpendicular, one molecule's positive rim meets the other's negative face and it is -4.6. The sign changes on the way, so the preference is not that one arrangement is weaker — it is that they are opposite. This is a molecule with no dipole moment at all.

Zero dipole is not no interaction

Benzene's dipole moment is exactly zero at every origin, and its quadrupole moment is large enough to decide a crystal structure. Two benzenes face to face repel by nine kilojoules a mole; edge to face they attract, and the sign changes on the way between.

shape · Dipole
ammonia's rotational levels, sorted by K. The rigid rotational levels of ammonia up to J = 4, each drawn at its computed energy and grouped by J. Within a group the levels are pushed apart by the second rotational constant, so it is plainly there in the level pattern.

The constant a spectrum cannot see

A symmetric top has two rotational constants and its microwave spectrum reports one of them. Not badly, not with difficulty: ammonia's A of 6.3406 wavenumbers appears in none of its lines at any J and any K, because the term it belongs to cancels exactly out of every transition. The molecule turns about that axis, the energy is real, and the measurement is blind to it.

spectra · Rotation
How far benzene is from its own group, against how far it has been pushed. The measure — the distance to the nearest structure with the ideal group — against the size of the distortion, for two ways of distorting the same molecule. Each curve is smooth and quadratic; the markers on it are where the point-group search changes its verdict, which happens at one step and says nothing about the steps either side of it.

How much symmetry is left

A point group is a verdict and every real structure fails it. Two distortions of benzene that are two per cent apart in how far they sit from D6h need tolerances 1.88 times apart before the search will call either of them D6h — and one tolerance, applied to six molecules, admits amounts of asymmetry differing by a factor of fifty-six.

symmetry · Point group
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
A photoelectron band is a filter, and the group chooses the filter. The Huang–Rhys factor of every vibration of five molecules under a change of geometry that lengthens every bond alike — which is what removing an electron from a non-degenerate orbital does. On a logarithmic scale spanning sixteen decades, eight modes carry the whole of it and the rest sit on the floor at arithmetic noise. Which ones is decided by the point group: only a totally symmetric vibration can appear, whatever the size of the change.

A band is a filter on the modes

A photoelectron band's vibrational structure reports the frequencies of a few of the ion's vibrations and is silent about the rest, and which few is decided by the point group before any geometry is known. Under a change of shape that lengthens every bond alike, methane's totally symmetric stretch gets a Huang–Rhys factor of 0.905 and its other eight modes get between 10⁻²⁸ and 10⁻³⁵.

spectra · Photoelectron
An effect that cannot distort a molecule, deciding how far it distorts. The energy along one distortion coordinate, three times. With only the first-order term the minimum is at 0.6; with only the second-order term there is no minimum away from zero at all, because the gap of 1.5 is above the critical 1 for a closed shell on its own. With both, the molecule distorts to 1.06 — well past the first-order answer — and gains 0.09 more than the two separate stabilisations add up to.

Two distortions in one coordinate

A second-order Jahn–Teller effect that cannot distort a molecule by itself — its gap is half again above the critical value — nearly doubles the distortion when a first-order effect is already acting. The molecule goes to 1.075 instead of 0.600 and gains twice the energy, and it does it while the gap the second-order term divides by is opening rather than closing.

shape · Peierls distortion
Three quarters, exactly, for every mode that is not totally symmetric. The depolarisation ratio of every Raman-active mode of five molecules, computed from a bond-polarisability model. 18 of the 26 sit on three quarters to better than a millionth, and they are exactly the modes that are not totally symmetric: the mean polarisability derivative is a trace, a trace is invariant, and an invariant has no derivative along any other species. The polarised ones below the line are the totally symmetric modes, and where they sit is a property of the model rather than of the group.

The one intensity symmetry does fix

Symmetry says which bands exist and declines to say how strong they are. It makes exactly one exception, and it is a ratio: every Raman band that is not totally symmetric is depolarised by exactly three quarters, whatever the molecule and whatever the model — and methane's symmetric stretch is polarised by exactly zero, because its group is cubic.

symmetry · Spectrum
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
A ratio that measures a distortion, and squares it first. How far ammonia's depolarised bands come off three quarters against how far one of its bonds has been stretched. Undistorted the departure is 3.1e-8, which is the rounding in the stored coordinates rather than a physical effect; at 0.1 Å it is 0.04239, and the slope is 1.999 — the departure goes as the square of the distortion, so a ratio measured to three decimals fixes a length to one and a half.

A ratio that squares what it measures

A depolarised Raman band sits at exactly three quarters because symmetry says its mean polarisability derivative is zero. Distort the molecule and it comes off — by 4.5 × 10⁻⁴ for a hundredth of an ångström and 0.042 for a tenth, going as the square of the distortion, which makes a ratio measured to three decimals a length known to one and a half.

spectra · Spectrum
Four tables, one answer, and a reason it could not be otherwise. The intensity–motion correlation — infrared intensity against how far the atoms move — computed with charges from four published electronegativity tables. Every molecule gives the same number on all four, to machine precision, because each is made of two elements: its charges are one number times a fixed pattern, a change of table changes only that number, and a rank correlation does not notice a rescaling. The dipole moments beside them do notice, which is the check that the tables are genuinely different.

The table that could not have mattered

Charges taken from one of four electronegativity tables invite a worry, because the tables disagree with each other. They do disagree — hydrogen cyanide's dipole runs over a factor of eleven between them — and for the molecules in question the worry could not have applied, because a molecule of two elements has charges that are one number times a fixed pattern and a rank correlation does not notice a rescaling.

shape · Dipole
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
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 gap that makes sixteen special does not move. The gap above the sixteen-electron closure of a square plane and above the eighteen-electron closure of an octahedron, against the π strength. The octahedron's is 3eσ − 4eπ and moves at every value; the square plane's is exactly 2eσ until the π strength reaches a quarter of the σ one, because the orbital that sets it is d(z²) and a square-planar ligand set has nothing of that symmetry to offer. Past the threshold the two are the same number, which is not a coincidence: beyond it the square plane's gap is set by d(xy) and the expression is the octahedron's.

The orbital a ligand cannot reach

The sixteen-electron count of a square plane is a statement about an energy rather than about symmetry matching, so it was the count that ought to be sensitive to a π channel where the eighteen-electron one is not. It is not sensitive either — and for a sharper reason. The orbital that sets its gap is d(z²), and a square-planar ligand set contains nothing of that symmetry, so the gap is exactly 2eσ until the π strength reaches a quarter of the σ one.

applied · Electron count
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
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
The orbit identity holds on all nineteen, and the formula it replaced on eight. For each molecule in the census under the radius rule: its number of totally symmetric vibrations, the corrected count — symmetric orbits less symmetric redundancies — and the usual formula, orbits less redundancies. The corrected count lands on the molecule's own count every time. The usual formula is right for 8 of 19, and for ferrocene under the new bond list it predicts minus sixty-six.

The census a bond rule was hiding

Every internal coordinate, redundancy and totally symmetric count here is built on a bond list, and the bond list came from a length cutoff that gave five molecules no bonds. Rebuilt on the radius rule, the census reaches nineteen molecules instead of fifteen, the orbit identity holds on every newcomer, ferrocene's coordinates finally span all its vibrations — and a different gap appears: no bond rule can give a square-planar centre its two out-of-plane vibrations.

symmetry · Point group
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 representationsSymmetry operationModel limitDegeneracyCharacter tableReduction formulaGroup orderSelection rulesConventionHypervalencyNormal modeVibrational modes

All concepts