Concept

Dipole moment — where it appears

The first moment of a charge distribution, which vanishes for any molecule whose point group forbids it. It is a property of the molecule only when the total charge is zero, and it is not what decides an infrared spectrum's strength.

Named by 21 essays across 6 fields — each of them below, with the objects they name alongside it.

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
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.

The dipole is not a sum of bonds

Adding bond dipoles as vectors gets the easy cases right and rests on a quantity with several incompatible definitions. The symmetry argument is exact, needs no electronegativities, and says when the answer must be zero.

wrong · Dipole
Four scales, four orderings. Each column ranks the elements by one electronegativity scale, most electronegative at the top, with a line joining each element across the columns. Every crossing is a pair of elements that two scales order differently.

Electronegativity is not one quantity

Four scales, four definitions, four sets of units, and a defence — "they correlate well" — that answers a question nobody asked. Two scales can correlate at 0.99 and still put hydrogen on the wrong side of carbon.

wrong · Electronegativity
Dipole selection rules in Td. 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.

Selection rules are one theorem

An integral over all space vanishes unless the integrand is totally symmetric. Every selection rule in spectroscopy is that sentence with a different integrand — and the rule of mutual exclusion falls out rather than being remembered.

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
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
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
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
The bond sum, the measurement, and what is left over. For each pyramid: the vector sum of three bond moments estimated from the electronegativity difference and the measured geometry, the measured dipole, and the difference between them. Positive is towards the lone pair. Ammonia's bonds point that way and nitrogen trifluoride's point the other, which is why the trifluoride's far more polar bonds give it a dipole six times smaller. The leftover is 0.58 D for ammonia and at least 1.48 D for the trifluoride, so it is not one lone pair's property.

The lone pair is not the missing term

Ammonia's dipole is 1.47 debye and nitrogen trifluoride's is 0.235, although the N–F bonds are far more polar than the N–H ones. The bond sums explain the reversal exactly and point in opposite directions — and the lone pair that is supposed to make up the difference has to be worth 0.58 debye in one molecule and at least 1.48 in the other.

shape · Dipole
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
The dipole moment, and how many bands there are. For each of five molecules: the dipole moment of the point-charge model, the number of modes whose dipole derivative does not vanish, and the largest derivative. The molecules with no dipole at all have the most active bands, which is the whole of the argument.

A dipole is not what an infrared spectrum sees

Carbon dioxide has no dipole moment at all and three of its four modes are infrared active. Methane has none and six of nine; boron trifluoride none and five of six. Water, which has the largest dipole of the five, has three modes and three bands — and its dipole predicted neither number.

shape · Dipole
What boron trifluoride's bands are strong in, and what they move. Every infrared-active mode of boron trifluoride, with its band strength and the root-mean-square displacement of its atoms in the zero point, each scaled to its own largest. The two do not order the modes the same way — the rank correlation between them is 0.2 — and the strongest band belongs to the mode at 719 cm⁻¹, in which 89.93 per cent of the motion is the lightest atom's. Every mode moves the same weighted amount of mass, exactly, so that is not what separates them either.

The mode that moves least radiates most

Boron trifluoride's strongest infrared band is the one in which the fluorines barely move: ninety per cent of the motion belongs to the boron, which is a fifth of the molecule's mass. The mode that moves the most mass is nine and a half times weaker. Across five molecules the rank correlation between band strength and how far the atoms actually go runs from +1 to −0.66, and every normal mode carries exactly the same weighted motion by construction.

shape · Dipole
A ninety per cent surface with a neighbour beside it. The contour enclosing 90 per cent of a one-electron ion's density at an effective charge of 1.6, drawn with no field as a circle and in a field of 0.05 atomic units as the closed curve. The surface moves out by 47.3 millibohr on the side the field pulls the density towards and in by the same amount on the far side — 2.84 per cent of its own radius. What the sphere encloses does not change to first order; only where the surface is does.

The surface a neighbour moves

An ion in a crystal sits in the field of the ion next to it, and that field moves its contour. The displacement has a closed form, it is checked against the polarisability it implies, and it turns out to be almost perfectly anti-correlated with the discrepancy it was proposed to explain — the pairs that need the most correction get the least.

orbitals · Contour
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
Twelve hydrogen bonds, four tables. The bond dipole of hydrogen against each partner, in debye, on each of the four tables after all four are anchored to the same hydrogen–fluorine separation. Positive is hydrogen at the positive end. A bond whose marks straddle the axis is one the tables disagree about the direction of, and there are 3 of them.

Four tables and one molecule to disagree about

A molecule of two elements is provably safe from the choice of electronegativity table, and a series down a group should land where the tables do disagree. It does. All four agree that hydrogen iodide is the exception — and they disagree about what its dipole is by 1.245 debye, which is two and a half times the 0.448 that was measured.

shape · Dipole
A functional with no interior maximum. The Boys functional against the mixing angle for a carbonyl, evaluated directly at a hundred and eighty-one angles. It is a quadratic in cos²θ − ½ with no linear term, so it is symmetric about forty-five degrees and its maximum is at the middle or at the ends and nowhere else. Here the coefficient is positive, so the best is at 0° — the canonical σ and π. There is no angle to search for, however unsymmetrical the molecule is.

The angle that does not have to be searched for

A carbonyl's two bent components have no symmetry making them equivalent, so the mixing that best localises them looks like something to search for and their s characters look like two different numbers. Neither happens. The localisation functional is a quadratic with no linear term, so its maximum is at forty-five degrees or at the ends — bent bonds or canonical ones, decided by one inequality, with nothing in between.

bonding · Hybrids
One number separates the disputed bonds from the agreed ones. Every bond in the collection, ordered by how big its electronegativity difference is as a fraction of each table's range. The six the tables disagree about are all below 0.0507; the 25 they agree about are all above 0.0584. Nothing lies between, and which elements a bond joins does not enter — a dispute is what happens when the difference is small enough that the tables' own disagreement about it is larger.

A dispute is a small difference

Four electronegativity tables disagree about the direction of a quarter of a set of hydrogen bonds, and the interhalogens look like the natural test: five compounds with no hydrogen in them, to say whether the disagreement is about one awkward element or about the whole idea. All four tables agree about every interhalogen. They agree because the differences are large, and that is not a fact about halogens.

shape · Dipole
What a rotation group buys over a single angle. The Boys functional at the canonical orbitals, at the best mixing of the two bonds with the lone pair left alone, and at the maximum over the whole three-dimensional rotation group. The first step is 11.70 per cent and the second, which no two-orbital treatment can reach, is a further 2.50.

An interior maximum a third orbital allows

Two orbitals related by a mirror plane give a Boys functional with no linear term, so it has no interior maximum and no angle is ever searched for. Add the oxygen lone pair and the search over a three-dimensional rotation group finds one — eight and a half degrees of lone pair mixed into two bent bonds, worth a further two and a half per cent that no pair of orbitals could reach.

bonding · Hybrids
The criterion is the reciprocal of the p amplitude. The two lone pairs' mixing criterion — twice the dipole between them over the separation of their centroids — against the p fraction of the outward hybrid. The curve is 1/√(p fraction), written down rather than fitted; the marks are the numerical integrals. They agree to 15 parts in a million at every hybrid, and the criterion never falls to one, so the mixed description wins at every s character there is.

The five figures were an identity

Two lone pairs satisfy the two-orbital mixing criterion by a margin of 1.732128, against √3 = 1.732051 — agreement to five figures on a number assembled from three integrals over a numerical grid. It is exact. The criterion is the reciprocal of the p amplitude of the outward hybrid, and everything else in the molecule cancels out of it.

bonding · Hybrids
Two quantities, and the best straight line between the two kinds of pair. Every pair the four electronegativity tables all cover, by how much the two elements differ and by how much the tables disagree about them. Filled points are pairs whose sign the tables dispute. The line is the boundary that misclassifies fewest — 3 of 153, against 6 for the best rule using the difference alone. It slopes upward, which is the mechanism: more dispute buys a larger difference and still leaves the sign in doubt.

Two numbers caught what one could not

No single threshold on the electronegativity difference separates the bond pairs whose polarity the four tables dispute from those they agree on — the best misses six of a hundred and fifty-three. Adding how much the tables disagree halves that to three and catches every disputed pair. And three is what four coin-flips produce: the rule flags nineteen pairs, an eighth of which should look agreed for no reason at all, which is 2.375 against the three observed.

shape · Dipole
Straight segments, and the curve fitted through their ends. Cl's energy against the charge it carries. The exact theory says the energy is straight between integers, with a kink at each one: the slope below the neutral atom is the electron affinity and the slope above it is the first ionisation energy, and the two are different numbers. Every quantity in this argument comes from the smooth curve fitted through those points instead — and the curve's second derivative, which is the hardness, is a property the segments do not have at all.

Four quantities go and one question stays

The exact theory says an atom's energy against electron count is straight segments between integers, and that model gets the alkali metals right for free — which is exactly where the fitted curves give lithium a negative electronegativity. What it costs is the hardness, the capacity, the electronegativity and equalisation, and what it leaves is a question whose answer is an integer.

wrong · Electronegativity

Named alongside it

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

Model limitElectronegativityPartial chargePolarityBond dipolePoint groupConventionLone pairPauling scaleRank correlationSymmetry operationClosed form

All concepts