Proving some conjectures on Kekulé numbers for certain benzenoids by using Chebyshev polynomials
Abstract.
In chemistry, Cyvin-Gutman enumerates Kekulé numbers for certain benzenoids and record it as on OEIS. This number is exactly the two variable array defined by the recursion , where for all nonnegative integers . Interestingly, this number also appeared in the context of weighted graphs, graph polytopes, magic labellings, and unit primitive matrices, studied by different authors. Several interesting conjectures were made on the OEIS. These conjectures are related to both the row and column generating function of . In this paper, give explicit formula of the column generating function, which is also the generating function studied by Bóna, Ju, and Yoshida. We also get trig function representations by using Chebyshev polynomials of the second kind. This allows us to prove all these conjectures.
Mathematic subject classification: Primary 05A15; Secondary 15A18, 05C78, 52B11.
Keywords: Chebyshev polynomials; Kekulé numbers; unit-primitive matrix; linear graphs.
1. Introduction
Throughout this paper, we use standard set notations for nonnegative integers, and positive integers, respectively. We also use and .
Definition 1.1.
Table 1 gives the first several values of as the entries.
0 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | … | |
0 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | … |
1 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | … |
2 | 1 | 3 | 6 | 10 | 15 | 21 | 28 | 36 | 45 | 55 | … |
3 | 1 | 5 | 14 | 30 | 55 | 91 | 140 | 204 | 285 | 385 | … |
4 | 1 | 8 | 31 | 85 | 190 | 371 | 658 | 1086 | 1695 | 2530 | … |
5 | 1 | 13 | 70 | 246 | 671 | 1547 | 3164 | 5916 | 10317 | 17017 | … |
⋮ | ⋮ | ⋮ | ⋮ | ⋮ | ⋮ | ⋮ | ⋮ | ⋮ | ⋮ |
One can find many interesting properties about on [9]. It counts certain chemistry structure, and several combinatorial structures as we shall introduce. Let
be the row and column generating function of , respectively. There are six conjectures related to and . We will state them in Section 2 after introducing some notations.
1.1. Kekulé structures
The number appeared in chemistry [3] as the number of Kekulé structures of the benzenoid hydrocarbon , where is a zigzag chain interpreted as tier condensed linear chains (rows) of hexagons each in a zigzag arrangement as in Figure 1.

The special case is the single structure of benzene (). In Figure 2, picture (1) illustrates , and picture (2) gives the two Kekulé structures regarded differently in chemistry.

The explicit definition of is too involved so we only give several of them in Figure 3. We cannot find a reference proving that .

1.2. Combinatorial Models
Let be a simple graph with vertex set and edge set . We will introduce three combinatorial models: i) Graph polytope studied in [8, 11, 15]; ii) Weighted graph studied in [1]; iii) Magic labellings of a graph studied in [13]. Though the concepts are for general graphs, we will focus on the linear graph (or path) with vertices.
The graph polytope associated to a simple graph is defined as
The dilation of by is denoted . The Ehrhart series of is defined by
A a weighted graph of with distribution is a triplet , where the weight of is . It is natural to define the weight of an edge to be . Let be the number of all weighted graphs of with a fixed upper bound for weight of each vertex and edge of . That is, for all and
(1.2) |
An interesting question is to compute the generating function of :
Let be a finite (undirected) graph with vertex set and edge set . We allow loops in so is also called a pseudo graph in the terminology of [6]. A magic labelling of with magic sum is a labelling of the edges in by nonnegative integers such that for each vertex , the weight of , defined to be the sum of labels of all edges incident to , is equal to . Denote by the number of magic labelling of with magic sum . More precisely, counts the number of maps satisfying
(1.3) |
An interesting question is compute the generating function
Finally, let be the order matrix defined by . It is called a unit-primitive matrix by Jeffery [7] in a different context.
The following result is claimed on [9], but we cannot find a real proof in the literature.
Theorem 1.2.
For , the number has the following interpretations.
-
(1)
The entry of the matrix , also equal to , where .
-
(2)
The number of weighted graphs of with a fixed upper bound .
-
(3)
The number of integer lattice points in the dilated graph polytope .
-
(4)
The number of magic labellings of the pseudo graph with magic sum , where is obtained from the linear graph by attaching one loop at each vertex.
Consequently in terms of generating functions, we have
The equivalence of (2), (3), (4) can be easily seen by an example of . By definition, is the number of -solutions of the system . The ’s are exactly the lattice points of the dilated graph polytope . Let . Then the system is translated to
which says the labelling as in Figure 4 is a magic labeling of .

To see that (2) is equivalent to (1), we describe as a walk on the finite state of the ’s: first choose , then choose to be any number in , since we have the restriction , and then choose to be any number in by the restriction . The transfer matrix from the state of to the state of is just , the unit primitive matrix of order . It then follows that .
The transfer matrix idea was used in [1], where weighted graphs were systematically enumerated and the following beautiful formula about was cited.
Theorem 1.3.
However, the cited paper was never finished (private communication), so it is necessary to give a proof.
1.3. Main Results
Our objectives in this paper is 4-folded.
Firstly, we give a proof of Theorem 1.2. For convenience, we use to denote the -th unit column vector in . Let . Then it is sufficient to prove the following.
Theorem 1.4.
For , we have
(1.4) |
Secondly, we give two proofs of Theorem 1.3. Further more, we obtain trig function representation.
Theorem 1.5.
For , we have
where .
Thirdly, we obtain a factorization of the characteristic polynomial of as follows, where throughout the paper, we use to denote the characteristic polynomial of an order matrix .
Theorem 1.6.
For a given positive integer , we have
Finally, we prove the six conjectures related to in Section 2.
1.4. Summary
This paper is organized as follows: In Section 2 we state the six conjectures after introducing some notations. Chebyshev polynomial of the second kind plays an important role in our development. Section 3 proves Theorem 1.4, an equivalent form of Theorem 1.2. The idea is to use matrix computation to derive certain recursion of . The idea is used to give a proof of Theorems 1.3, but seems irrelevant to the other sections. Section 4 studies many properties of the unit primitive matrix , especially its eigenvalues. As consequences, we give the proof of Theorems 1.5-1.6 and Conjecture 1. We also give explicit formula of the column generating function . In Section 5, we first use the magic labelling model to sketch a proof of Conjectures 2-3, which are related to the row generating function . Conjectures 4-6 are about the numerator of . We prove them in later subsections by using the explicit formulas of the column generating function .
2. Six Conjectures Related to
We will introduce 6 interesting conjectures related to the unit-primitive matrix and the sequence . Their proofs will be given in later sections.
Our development highly relies on Chebyshev polynomial of the second kind (CPS for short), which is defined recursively by
We also need the well-known formula (see, e.g., [10]):
(2.1) |
Many results are related to the polynomials defined by
(2.2) |
The first conjecture is related to the unit-primitive matrix .
Conjecture 1.
(A187660 [9]). (i) For positive integer . The characteristic polynomial of the unit-primitive matrix is:
(2.3) |
(ii) The eigenvalues of are given by , where for .
The other 5 conjectures are all related to the sequence defined by (1.1).
Let be the Euler number [12, Section 3.16] with exponential generating function
The following result was observed in [9].
Lemma 2.1.
For fixed nonnegative integer , is a polynomial in of degree with leading coefficient . Therefore the -th row generating function of is of the following form
where is a polynomial of degree no more than . Here we start with row .
Proof.
The reason is so simple that we include it here. For the first part, let . We need to show that with and the leading coefficient is . The assertion clearly holds for , since . Assume the lemma holds for all . To show the assertion holds for , we rewrite (1.1) as
That is, the divided difference of is a sum of polynomials of degree with leading coefficient
by the induction hypothesis. Therefore is a polynomial in of degree with leading coefficient . It is in fact follows by equating coefficient of in the identity
The second part follows by classical theory on rational functions. See [12].
Simple calculation shows that . The second conjecture gives more details on .
Conjecture 2.
The array is given by the sequence A205497 in [9]. Christopher H. Gribble kindly calculated the first 100 antidiagonals of the array which starts as in Table 2.
0 | 1 | 2 | 3 | 4 | 5 | … | |
0 | 1 | 1 | 1 | 1 | 1 | 1 | … |
1 | 1 | 3 | 7 | 14 | 26 | 46 | … |
2 | 1 | 7 | 31 | 109 | 334 | 937 | … |
3 | 1 | 14 | 109 | 623 | 2951 | 12331 | … |
4 | 1 | 26 | 334 | 2951 | 20641 | 123216 | … |
5 | 1 | 46 | 937 | 12331 | 123216 | 1019051 | … |
⋮ | ⋮ | ⋮ | ⋮ | ⋮ | ⋮ | ⋮ |
There are several conjectures about .
Conjecture 3.
(A205497 [9]). , for all and ; that is, is symmetric about the central terms .
Conjecture 4.
Conjecture 5.
(A205497 [9]). The generation functions from column 0 to 4 of are the following 5 in order.
-
(0)
;
-
(1)
;
-
(2)
;
-
(3)
;
-
(4)
.
Here
3. Proofs of Theorems 1.3 and 1.4
In this section, we first prove Theorem 1.4 by using matrix computations. Then we use similar idea to give our first proof of Theorem 1.3. The ideas in this section are irrelevant to the other sections.
We use the following notations: , and (the all matrix). The basic properties of these order matrices are given in the following lemma. They will be used in the next subsection.
Lemma 3.1.
For a given positive integer , the following equations all hold true.
-
(1)
and ;
-
(2)
;
-
(3)
;
-
(4)
;
-
(5)
;
-
(6)
;
-
(7)
, where .
Proof.
The first six equalities are straightforward, so we only prove the seventh equality. By using block matrix operation, we have
3.1. Proof of Theorem 1.4
To prove Theorem 1.4, it is sufficient to show that satisfy the same recursion (1.1) as for . This is Corollary 3.6 below.
We need some lemmas.
Lemma 3.2.
Given three positive integers , and with , we have
(3.1) |
Lemma 3.3.
For given two positive integers and , we have
Proof.
We discuss by the parity of as follows.
If is odd, then . We have
Lemma 3.4.
For given two positive integers and , we have
Proof.
By adding Equation (3.1) with respect to , we get
(3.2) |
This is just a equivalent form of the lemma.
A direct consequence of Lemma 3.4 is the following.
Theorem 3.5.
Let and be two positive integers. Then for any vectors and , we have
In particular, setting and gives the following corollary.
Corollary 3.6.
For positive integers and , we have
(3.3) |
3.2. Proof of Theorem 1.3
We will prove a more general result by using similar technique as in the previous subsection.
Lemma 3.7.
For given three positive integers , and , we have
Lemma 3.8.
For given two positive integers and , we have
Proof.
Lemma 3.9.
For given two positive integers and , we have
(3.5) |
Proof.
Theorem 3.10.
Let and be positive integers. Then for any vectors and , we have
(3.7) |
Proof.
Multiply Equation (3.5) from the left by and from the right by .
Corollary 3.11.
For and , we have
Proof.
First Proof of Theorem 1.3.
It suffices to show that
(3.8) |
which is equivalent to
Put in the formula
and equate coefficient of , we need to prove
which is just Corollary 3.11 (replacing by ). This completes the proof.
Define . Then
Theorem 3.12.
For a given positive integer , we have
(3.9) | ||||
Proof.
Corollary 3.13.
For a given positive integer , we have
Let with in Corollary 3.13. We get the following corollary.
Corollary 3.14.
For a given positive integer , we have
where and is the dimensional vector obtained by removing the last component of .
4. Some results about
From now on, we will consider instead of in last section.
4.1. The Characteristic polynomial of
Recall that is the unit primitive matrix of order . We need to introduce two closely related matrix and and their relation to the CPS . Let be an matrix with . Damianou give the following result.
Theorem 4.1.
(Damianou [4]). For a given positive integer , we have .
Let be the matrix with entries We will use the following fact.
Fact 4.2.
(Jeffery [7]). For , we have .
We have the following conclusion.
Lemma 4.3.
For a given positive integer , we have
-
(1)
, where ;
-
(2)
;
-
(3)
.
Proof.
Comparing the recursions in Lemma 4.3 gives the following result.
Lemma 4.4.
For a given positive integer , we have
(4.1) |
Proof.
We prove by induction on .
Lemma 4.5.
For a given positive integer , we have
Proof.
where and .
Lemma 4.6.
For a given positive integer , we have
Compare with the definition of in (2.2), we obtain the following result.
Corollary 4.7.
For a given positive integer , we have
Now, we give all solution of the equation as follows.
Lemma 4.8.
For a given positive integer , has distinct eigenvalues where .
Proof.
Lemma 4.9.
For a given positive integer , the unit-primitive matrix has distinct eigenvalues
where .
Recall Fact 4.2 says that . Then by Lemmas 4.8 and 4.9, we get the following result, which can also be obtained by direct calculation.
Corollary 4.10.
For , we have
where and with .
We have the following result which is useful for asymptotic analysis.
Lemma 4.11.
For , the eigenvalues of are ordered as follows.
-
(1)
If is odd, then
-
(2)
If is even, then
Moreover, the spectral radius of is given by the formula
Proof.
Observe that the function is monotonically decreasing in the interval . The first statement is straightforward.
By comparing with when is odd, and similarly when is even, we see that for all .
Finally, direction computation gives
This completes the proof.
We finish this subsection by the following byproduct by direct computation.
Proposition 4.12.
For a given positive integer , and , we have
4.2. Some results about and the proof of Theorem 1.5
In this subsection, our goal is to give some results about and prove Theorem 1.5. Our starting point is the determinant formula proved in Corollary 4.7.
We use the following notations: and is the -th unit column vector in ; for an order matrix , we denote by the adjoint matrix of . It is clear that is just the entry of , or the -minor of .
Lemma 4.13.
For , we have
Proof.
Observe that is just the sum of the first column entries of . Then it is standard to rewrite and compute as follows.
(Add the multiple of column 1 by to all the other columns) | |||
Similar determinant computation gives the following result as a byproduct.
Proposition 4.14.
For , we have
Combining the above with for , we obtain explicit diagonalization of as follows.
Corollary 4.15.
For a given positive integer and , the unit eigenvector of with respect to the eigenvalue is
where , and
Consequently, is an orthogonal matrix and .
The following result follows by the explicit formula of in (2.2), but we will give a determinant proof.
Lemma 4.16.
For , we have
Proof.
We have
where is obtained from by factoring out from column 1 and then applying Lemma 4.13, and is obtained from by expanding along the two boxed entries in the determinant.
A direct consequence of Lemma 4.16 is the following.
Corollary 4.17.
For , we have
Now we give explicit formula of and reprove Theorem 1.3.
Theorem 4.18.
Next we derive a trig representation of with the help of .
Lemma 4.19.
Let . Then we have
Thus has distinct roots , where .
Lemma 4.20.
For , we have
where .
Proof of Theorem 1.5.
We have
where and so that we choose .
Corollary 4.21.
For , the partial fraction decomposition of is:
(4.3) |
where with for . Moreover, , and asymptotically we have
Proof.
For a particular , the constant can be computed by using L’Hospital’s rule, where we need the relation and .
In particular, it is an easy exercise in calculus to show that
Remark 4.22.
Let be the graph of a -cycle with . It was shown in [1] that , and
Then we can obtain more explicit formula of . Moreover, we have
5. Some results on the generating function of
5.1. Proof of Conjectures 2-3
If we assume Theorem 1.2 holds true, then has been studied. For instance, [1, Corollary 3.8] asserts that
for some symmetric polynomial of degree at most . Here by saying that is symmetric, we mean that if . Such is also called palindromic in some literature. Indeed Bona et. al. gave a description of when is a simple bipartite graph in [1, Theorem 3.6]. But they seemed to be unaware of Conjectures 2-3 and didn’t study .
Lee et. al. [8] studied the Ehrhart series of graph polytopes and claimed that Conjectures 2-3 are consequences of their Theorem 4 by showing that is an -dimensional regular positive reflexive polytope with parameter (see the paper for the concepts). Their claim is true, but need to modular Theorem 1.2.
The two conjectures can also be attacked by the magic labelling model. Firstly, Stanley [13] studied magic labellings of general pseudo graphs and give a characterization of . In particular, has denominator if the graph obtained by removing all loops from is bipartite. Since removing all loops from is just , is of the desired form .
For details of the numerator , we would like to introduce Stanley’s Reciprocity Theorem, which is a more general result and seems easier to use. We basically follow [EC1, Chapter 4.6].
Let be an by matrix with integer entries. The null space of is denoted , which is also the solution space of the homogeneous linear Diophantine system . The -solution set forms an additive monoid (semigroup with a unit). Stanly’s Reciprocity Theorem [13][Theorem 4.1] gives a nice connection between the following two generating functions:
For further references and generalizations, see [14].
Theorem 5.1.
(Stanley’s Reciprocity Theorem). Let be an by integral matrix of full rank . If there is at least one , then we have as rational functions
Sketched Proof of Conjectures 2-3.
By Theorem 1.2 and the discussion above, we have shown
To prove Conjectures 2-3, it is sufficient to show that
This will be explained by Stanley’s Reciprocity Theorem.
Firstly, the system of homogeneous linear Diophantine equations is given by
See Figure 4 for the case. Secondly, the generating function refers to
and similarly for . It is clear that . Thirdly, the vector belongs to so that Stanley’s Reciprocity Theorem applies. Finally, observe that . It follows that , and consequently
as desired.
It is worth mentioning that Chen et al [5] proved that is unimodal.
5.2. Proof of Conjecture 4
Though is defined using the row generating function , the proof of Conjecture 4 relies on the column generating function .
Firstly, we need to represent in terms of .
Lemma 5.2.
For , we have
(5.1) |
Note that for .
Proof.
The lemma follows by comparing the coefficients of on both sides of
Define . Then, we get the following lemma.
Lemma 5.3.
For and , we have
Proof.
In terms of we obtain:
Theorem 5.4.
Proof.
To prove Conjecture 4, we need two more lemmas. Firstly let us define the degree of a rational function to be .
Lemma 5.5.
Let and be any two nonzero rational functions. Then we have
-
(1)
, and we always have the equality if ;
-
(2)
;
-
(3)
. Consequently, .
Proof.
The first two items are obvious. The third one follows by the quotient rule of derivatives. More precisely, write . Then
Item 3 follows since .
Lemma 5.6.
For given , we have .
Proof.
By Theorem 4.18, it suffice to show that .
By the explicit formula of in , we have
where is a polynomial of degree at most . This completes the proof.
Proof of Conjecture 4.
By Theorem 5.4, we need to analyze the property of each summand.
For the term for , has degree and denominator .
For each term for with , clearly has denominator . By Lemma 5.6, it has degree
Thus
It follows that .
By taking common denominators, we see that
for some polynomial . This proved part (1).
Next, the degree of the displayed denominator of is equal to
This proves part (3).
Finally,
This proves part (2).
Remark 5.7.
From the proof, we see that in general need not be coprime to the displayed denominator. Indeed, the degree of the denominator of in Equation 2.4 is 120, but our computation by Maple shows that the degree of the denominator of is 118. The reason is that and have a common factor , where and .
5.3. Proof of Conjecture 5
By using Theorem 5.4, Maple can easily produce for ?. However the result becomes too complex to print here, so we only do the cases for . Conjecture 5 then follows by our computation.
Example 5.8.
. This follows easily by for .
Example 5.9.
.
Proof.
Example 5.10.
.
Proof.
Example 5.11.
where
Proof.
Example 5.12.
where
Proof.
5.4. Proof of Conjecture 6
Our proof relies on Corollary 4.21, we first give a lemma.
Lemma 5.13.
For , we have
Acknowledgments: The authors would like to thank Bóna for helpful conversations.
References
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