A261340 -id:A261340 - cp's OEIS frontend

A000598 Number of rooted ternary trees with n nodes; number of n-carbon alkyl radicals C(n)H(2n+1) ignoring stereoisomers.

1, 1, 1, 2, 4, 8, 17, 39, 89, 211, 507, 1238, 3057, 7639, 19241, 48865, 124906, 321198, 830219, 2156010, 5622109, 14715813, 38649152, 101821927, 269010485, 712566567, 1891993344, 5034704828, 13425117806, 35866550869, 95991365288, 257332864506, 690928354105

Offset: 0

N. J. A. Sloane

Number of unlabeled rooted trees in which each node has out-degree <= 3.
Ignoring stereoisomers means that the children of a node are unordered. They can be permuted in any way and it is still the same tree. See A000625 for the analogous sequence with stereoisomers counted.
In alkanes every carbon has valence exactly 4 and every hydrogen has valence exactly 1. But the trees considered here are just the carbon "skeletons" (with all the hydrogen atoms stripped off) so now each carbon bonds to 1 to 4 other carbons. The out-degree is then <= 3.
Other descriptions of this sequence: quartic planted trees with n nodes; ternary rooted trees with n nodes and height at most 3.
The number of aliphatic amino acids with n carbon atoms in the side chain, and no rings or double bonds, has the same growth as this sequence. - Konrad Gruetzmann, Aug 13 2012

			From _Joerg Arndt_, Feb 25 2017: (Start)
The a(5) = 8 rooted trees with 5 nodes and out-degrees <= 3 are:
:         level sequence    out-degrees (dots for zeros)
:     1:  [ 0 1 2 3 4 ]    [ 1 1 1 1 . ]
:  O--o--o--o--o
:
:     2:  [ 0 1 2 3 3 ]    [ 1 1 2 . . ]
:  O--o--o--o
:        .--o
:
:     3:  [ 0 1 2 3 2 ]    [ 1 2 1 . . ]
:  O--o--o--o
:     .--o
:
:     4:  [ 0 1 2 3 1 ]    [ 2 1 1 . . ]
:  O--o--o--o
:  .--o
:
:     5:  [ 0 1 2 2 2 ]    [ 1 3 . . . ]
:  O--o--o
:     .--o
:     .--o
:
:     6:  [ 0 1 2 2 1 ]    [ 2 2 . . . ]
:  O--o--o
:     .--o
:  .--o
:
:     7:  [ 0 1 2 1 2 ]    [ 2 1 . 1 . ]
:  O--o--o
:  .--o--o
:
:     8:  [ 0 1 2 1 1 ]    [ 3 1 . . . ]
:  O--o--o
:  .--o
:  .--o
(End)

N. L. Biggs et al., Graph Theory 1736-1936, Oxford, 1976, p. 62 (quoting Cayley, who is wrong).
A. Cayley, On the mathematical theory of isomers, Phil. Mag. vol. 67 (1874), 444-447 (a(6) is wrong).
J. L. Faulon, D. Visco and D. Roe, Enumerating Molecules, In: Reviews in Computational Chemistry Vol. 21, Ed. K. Lipkowitz, Wiley-VCH, 2005.
R. A. Fisher, Contributions to Mathematical Statistics, Wiley, 1950, 41.397.
J. L. Gross and J. Yellen, eds., Handbook of Graph Theory, CRC Press, 2004; p. 529.
Handbook of Combinatorics, North-Holland '95, p. 1963.
Knop, Mueller, Szymanski and Trinajstich, Computer generation of certain classes of molecules.
D. Perry, The number of structural isomers ..., J. Amer. Chem. Soc. 54 (1932), 2918-2920.
G. Polya, Mathematical and Plausible Reasoning, Vol. 1 Prob. 4 pp. 85; 233.
N. J. A. Sloane, A Handbook of Integer Sequences, Academic Press, 1973 (includes this sequence).
N. J. A. Sloane and Simon Plouffe, The Encyclopedia of Integer Sequences, Academic Press, 1995 (includes this sequence).

Vaclav Kotesovec, Table of n, a(n) for n = 0..1000 (first 200 terms from N. J. A. Sloane)
Jean-François Alcover, Mathematica program translated from N. J. A. Sloane's Maple program for A000022, A000200, A000598, A000602, A000678.
A. T. Balaban, J. W. Kennedy and L. V. Quintas, The number of alkanes having n carbons and a longest chain of length d, J. Chem. Education, 65 (1988), 304-313.
A. Cayley, On the mathematical theory of isomers, Phil. Mag. vol. 67 (1874), 444-447 (a(6) is wrong). (Annotated scanned copy)
Frederic Chyzak, Enumerating alcohols and other classes of chemical molecules.
Maximilian Fichtner, K. Voigt, and S. Schuster, The tip and hidden part of the iceberg: Proteinogenic and non-proteinogenic aliphatic amino acids, Biochimica et Biophysica Acta (BBA)-General, 2016, Volume 1861, Issue 1, Part A, January 2017, pp. 3258-3269.
P. Flajolet and R. Sedgewick, Analytic Combinatorics, 2009; see page 478.
K. Grützmann, S. Böcker, and S. Schuster, Combinatorics of aliphatic amino acids, Naturwissenschaften, Vol. 98, No. 1, 79-86, 2011.
H. R. Henze and C. M. Blair, The number of structurally isomeric alcohols of the methanol series, J. Amer. Chem. Soc., 53 (8) (1931), 3042-3046.
H. R. Henze and C. M. Blair, The number of structurally isomeric alcohols of the methanol series, J. Amer. Chem. Soc., 53 (8) (1931), 3042-3045. (Annotated scanned copy)
INRIA Algorithms Project, Encyclopedia of Combinatorial Structures 1.
P. Leroux and B. Miloudi, Généralisations de la formule d'Otter, Ann. Sci. Math. Québec, Vol. 16, No. 1, pp. 53-80, 1992. (Annotated scanned copy)
Camden A. Parks and James B. Hendrickson, Enumeration of monocyclic and bicyclic carbon skeletons, J. Chem. Inf. Comput. Sci., vol. 31, 334-339 (1991).
D. Perry, The number of structural isomers of certain homologs of methane and methanol, J. Amer. Chem. Soc. 54 (1932), 2918-2920. [Gives a(60) correctly.] (Annotated scanned copy)
G. Polya, Algebraische Berechnung der Anzahl der Isomeren einiger organischer Verbindungen, Zeit. f. Kristall., 93 (1936), 415-443; Table I, line 2.
G. Polya, Algebraische Berechnung der Anzahl der Isomeren einiger organischer Verbindungen, Zeit. f. Kristall., 93 (1936), 415-443; Table I, line 2. (Annotated scanned copy)
R. C. Read, The Enumeration of Acyclic Chemical Compounds, pp. 25-61 of A. T. Balaban, ed., Chemical Applications of Graph Theory, Ac. Press, 1976. [Annotated scanned copy] See p. 20, Eq. (G); p. 27, Eq. 2.1.
Marko Riedel, Chris Grossack, Counting trees with a degree constraint, Math StackExchange.
R. W. Robinson, F. Harary and A. T. Balaban, Numbers of chiral and achiral alkanes and monosubstituted alkanes, Tetrahedron 32 (3) (1976), 355-361.
R. W. Robinson, F. Harary and A. T. Balaban, Numbers of chiral and achiral alkanes and monosubstituted alkanes, Tetrahedron 32 (3) (1976), 355-361. (Annotated scanned copy)
Hugo Schiff, Zur Statistik chemischer Verbindungen, Berichte der Deutschen Chemischen Gesellschaft, Vol. 8, pp. 1542-1547, 1875. [Annotated scanned copy]
N. J. A. Sloane, Maple program and first 60 terms for A000022, A000200, A000598, A000602, A000678.
N. Trinajstich, Z. Jerievi, J. V. Knop, W. R. Muller and K. Szymanski, Computer Generation of Isomeric Structures, Pure & Appl. Chem., Vol. 55, No. 2, pp. 379-390, 1983.
Wikipedia, Polya's enumeration theorem.
Index entries for sequences related to rooted trees
Index entries for sequences related to trees

Cf. A000599, A000600, A000602, A000625, A000628, A000678, A010372, A010373, A086194, A086200, A261340.
Cf. A292553, A292554, A292555, A292556.
Cf. A000081, A001190, A014591, A032305, A295461, A298118, A298120, A298204, A298422, A298426.
Column k=3 of A299038.

N := 45; G000598 := 0: i := 0: while i<(N+1) do G000598 := series(1+z*(G000598^3/6+subs(z=z^2,G000598)*G000598/2+subs(z=z^3,G000598)/3)+O(z^(N+1)),z,N+1): t[ i ] := G000598: i := i+1: od: A000598 := n->coeff(G000598,z,n);
# Another Maple program for g.f. G000598:
G000598 := 1; f := proc(n) global G000598; coeff(series(1+(1/6)*x*(G000598^3+3*G000598*subs(x=x^2,G000598)+2*subs(x=x^3,G000598)),x, n+1),x,n); end; for n from 1 to 50 do G000598 := series(G000598+f(n)*x^n,x,n+1); od; G000598;
spec := [S, {Z=Atom, S=Union(Z, Prod(Z, Set(S, card=3)))}, unlabeled]: [seq(combstruct[count](spec, size=n), n=0..20)];

m = 45; Clear[f]; f[1, x_] := 1+x; f[n_, x_] := f[n, x] = Expand[1+x*(f[n-1, x]^3/6 + f[n-1, x^2]*f[n-1, x]/2 + f[n-1, x^3]/3)][[1 ;; n]]; Do[f[n, x], {n, 2, m}]; CoefficientList[f[m, x], x]
(* second program (after N. J. A. Sloane): *)
m = 45; gf[] = 0; Do[gf[z] = 1 + z*(gf[z]^3/6 + gf[z^2]*gf[z]/2 + gf[z^3]/3) + O[z]^m // Normal, m]; CoefficientList[gf[z], z]  (* Jean-François Alcover, Sep 23 2014, updated Jan 11 2018 *)
b[0, i_, t_, k_] = 1; m = 3; (* m = maximum children *)
b[n_,i_,t_,k_]:= b[n,i,t,k]= If[i<1,0,
  Sum[Binomial[b[i-1, i-1, k, k] + j-1, j]*
  b[n-i*j, i-1, t-j, k], {j, 0, Min[t, n/i]}]];
Join[{1},Table[b[n-1, n-1, m, m], {n, 1, 35}]] (* Robert A. Russell, Dec 27 2022 *)

seq(n)={my(g=O(x)); for(n=1, n, g = 1 + x*(g^3/6 + subst(g,x,x^2)*g/2 + subst(g,x,x^3)/3) + O(x^n)); Vec(g)} \\ Andrew Howroyd, May 22 2018

def seq(n):
    B = PolynomialRing(QQ, 't', n+1);t = B.gens()
    R. = B[[]]
    T = sum([t[i] * z^i for i in range(1,n+1)]) + O(z^(n+1))
    lhs, rhs = T, 1 + z/6 * (T(z)^3 + 3*T(z)*T(z^2) + 2*T(z^3))
    I = B.ideal([lhs.coefficients()[i] - rhs.coefficients()[i] for i in range(n)])
    return [I.reduce(t[i]) for i in range(1,n+1)]
seq(33) # Chris Grossack, Mar 31 2025

G.f. A(x) satisfies A(x) = 1 + (1/6)*x*(A(x)^3 + 3*A(x)*A(x^2) + 2*A(x^3)).

a(n) ~ c * d^n / n^(3/2), where d = 1/A261340 = 2.8154600331761507465266167782426995425365065396907..., c = 0.517875906458893536993162356992854345458168348098... . - Vaclav Kotesovec, Aug 15 2015

Additional comments from Steve Strand (snstrand(AT)comcast.net), Aug 20 2003

A000642 a(1)=0; for n>1, a(n) = number of isomeric hydrocarbons of the acetylene series with carbon content n.

Original entry on oeis.org

0, 1, 1, 2, 3, 7, 14, 32, 72, 171, 405, 989, 2426, 6045, 15167, 38422, 97925, 251275, 648061, 1679869, 4372872, 11428365, 29972078, 78859809, 208094977, 550603722, 1460457242, 3882682803, 10344102122, 27612603765, 73844151259, 197818389539

Offset: 1

N. J. A. Sloane

The former definition was "Number of alkyl derivatives of acetylene X^{II} C_n H_{2n+2} with n carbon atoms" with offset 0.

a(n+1) is the number of rooted trees with n nodes and out-degree <= 2 on the root and out-degree <= 3 on all other nodes. See illustration of initial terms. - Washington Bomfim, Nov 28 2020

N. J. A. Sloane, A Handbook of Integer Sequences, Academic Press, 1973 (includes this sequence).
N. J. A. Sloane and Simon Plouffe, The Encyclopedia of Integer Sequences, Academic Press, 1995 (includes this sequence).

T. D. Noe, Table of n, a(n) for n = 1..201 (offset adapted by _Georg Fischer_, Jan 31 2019)
Washington Bomfim, Illustration of initial terms
D. D. Coffman, C. M. Blair and H. R. Henze, The number of structurally isomeric hydrocarbons of the acetylene series, J. Amer. Chem. Soc., 55 (1933), 252-253.
D. D. Coffman, C. M. Blair and H. R. Henze, The number of structurally isomeric hydrocarbons of the acetylene series, J. Amer. Chem. Soc., 55 (1933), 252-253. (Annotated scanned copy)
Jean-Loup Faulon, Donald P. Visco Jr., Diana Roe, Enumerating Molecules, In: Reviews in Computational Chemistry Vol. 21, Ed. K. Lipkowitz, Wiley-VCH, 2005.
R. J. Mathar, Illustration for graphs up to 6 carbons
G. Polya, Algebraische Berechnung der Anzahl der Isomeren einiger organischer Verbindungen, Zeit. f. Kristall., 93 (1936), 415-443; line 8 of Table I, "R" of Table IV.
G. Polya, Algebraische Berechnung der Anzahl der Isomeren einiger organischer Verbindungen, Zeit. f. Kristall., 93 (1936), 415-443; line 8 of Table I, "R" of Table IV. (Annotated scanned copy)
R. C. Read, Some recent results in chemical enumeration, Lect. Notes Math. 303 (1972), 243-259.
R. C. Read, The Enumeration of Acyclic Chemical Compounds, pp. 25-61 of A. T. Balaban, ed., Chemical Applications of Graph Theory, Ac. Press, 1976. [Annotated scanned copy] See p. 28.
N. Trinajstich, Z. Jerievi, J. V. Knop, W. R. Muller and K. Szymanski, Computer Generation of Isomeric Structures, Pure & Appl. Chem., Vol. 55, No. 2, pp. 379-390, 1983.
Index entries for sequences related to rooted trees

Cf. A000598, A002094.

terms = 32; B[] = 0; Do[B[x] = 1 + (1/6)*x*(B[x]^3 + 3*B[x]*B[x^2] + 2*B[x^3]) + O[x]^terms // Normal, terms];
A[x_] = (1/2)*x*(B[x^2] + B[x]^2) + O[x]^terms;
CoefficientList[A[x], x] (* Jean-François Alcover, Jun 28 2012, updated Jan 10 2018 *)

\\ here G(n) is A000598 as g.f.
G(n)={my(g=O(x)); for(n=1, n, g = 1 + x*(g^3/6 + subst(g, x, x^2)*g/2 + subst(g, x, x^3)/3) + O(x^n)); g}
seq(n)={my(g=G(n)); Vec(subst(g,x,x^2) + g^2, -(n+1))/2} \\ Andrew Howroyd, Nov 28 2020

G.f.: A(x)=(1/2)*x*(B(x^2)+B(x)^2), where B(x) = g.f. for A000598.

a(n) ~ c * d^n / n^(3/2), where d = 1/A261340 = 2.815460033176... and c = 0.13833565403175156418512996853... - Vaclav Kotesovec, Feb 11 2019

I changed the definition and offset so as to agree with Coffman et al. (1933). - N. J. A. Sloane, Jan 13 2019

A121331 Number of bridged bicyclic skeletons with n carbon atoms (see Parks et al. for precise definition).

Original entry on oeis.org

1, 2, 6, 15, 39, 99, 258, 671, 1762, 4657, 12372, 33036, 88590, 238483, 644045, 1744542, 4737341, 12894158, 35165994, 96083192, 262951511, 720685274, 1977846334, 5434588909, 14949284828, 41163690109, 113451949753, 312955174089, 863965424349, 2386874582238

Offset: 5

N. J. A. Sloane, Aug 27 2006

nonn

Equivalently, the number of connected graphs on n unlabeled nodes with exactly 2 cycles of the same even length joined along half their length and all nodes having degree at most 4. The resulting graph will have three equal length cycles. - Andrew Howroyd, May 25 2018

			From _Andrew Howroyd_, May 25 2018: (Start)
Illustration of graphs for n=5 and n=6:
    o          o--o       o
   /|\        /|\        /|\
  o o o      o o o      o o o--o
   \|/        \|/        \|/
    o          o          o
.
Illustration of graphs for n=7:
    o--o      o--o--o   o--o        o        o          o   o
   /|\       /|\       /|\         /|\      /|\        /|\ /
  o o o     o o o     o o o--o    o o o    o o o--o   o o o
   \|/       \|/       \|/       / \|/ \    \|/   |    \|/ \
    o--o      o         o       o   o   o    o    o     o   o
(End)

Andrew Howroyd, Table of n, a(n) for n = 5..200
Camden A. Parks and James B. Hendrickson, Enumeration of monocyclic and bicyclic carbon skeletons, J. Chem. Inf. Comput. Sci., vol. 31, 334-339 (1991).

Cf. A121158, A121162, A121165, A305132.

G[n_] := Module[{g}, g[] = 0; Do[g[x] = 1 + x*(g[x]^3/6 + g[x^2]*g[x]/2 + g[x^3]/3) + O[x]^n // Normal, {n}]; g[x]];
C1[n_] := Sum[(d1^(3*k)+3*d1^k*d2^k + 2*d3^k), {k, 1, Quotient[n, 3]}]/12;
C2[n_] := Sum[(d1^Mod[k, 2]*d2^Quotient[k, 2])^3 + 3*d1^Mod[k, 2]* d2^(Quotient[k, 2] + k) + 2*d3^Mod[k, 2]*d6^Quotient[k, 2], {k, 1, Quotient[n, 3]}]/12;
seq[n_] := Module[{s, d, g}, s = G[n]; d = x*(s^2 + (s /. x -> x^2))/2; g[p_, e_] := Normal[(p+O[x]^(Quotient[n, e]+1))] /. x :> x^e; g[s, 1]^2* (C1[n-2] /. Thread[{d1, d2, d3} :> {g[d, 1], g[d, 2], g[d, 3]}]) + g[s, 2]*(C2[n-2] /. Thread[{d1, d2, d3, d6} :> {g[d, 1], g[d, 2], g[d, 3], g[d, 6]}]) + O[x]^n] // CoefficientList[#, x]& // Drop[#, 3]&;
seq[33] (* Jean-François Alcover, Sep 08 2019, after Andrew Howroyd *)

\\ here G is A000598 as series
G(n)={my(g=O(x)); for(n=1, n, g = 1 + x*(g^3/6 + subst(g, x, x^2)*g/2 + subst(g, x, x^3)/3) + O(x^n)); g}
C1(n)={sum(k=1, n\3, (d1^(3*k) + 3*d1^k*d2^k + 2*d3^k))/12}
C2(n)={sum(k=1, n\3, (d1^(k%2)*d2^(k\2))^3 + 3*d1^(k%2)*d2^(k\2+k) + 2*d3^(k%2)*d6^(k\2))/12}
seq(n)={my(s=G(n)); my(d=x*(s^2+subst(s, x, x^2))/2); my(g(p,e)=subst(p + O(x*x^(n\e)), x, x^e)); Vec(O(x^n/x) + g(s,1)^2*substvec(C1(n-2),[d1,d2,d3],[g(d,1), g(d,2), g(d,3)]) + g(s,2)*substvec(C2(n-2), [d1,d2,d3,d6], [g(d,1), g(d,2), g(d,3), g(d,6)]))} \\ Andrew Howroyd, May 25 2018

a(n) ~ c * d^n / sqrt(n), where d = 1/A261340 = 2.815460033176150746526616778..., c = 0.0064202170754... . - Vaclav Kotesovec, Sep 08 2019

Corrected by Franklin T. Adams-Watters and T. D. Noe, Oct 25 2006

a(24) corrected and terms a(26) and beyond from Andrew Howroyd, May 25 2018

cp's OEIS Frontend

A000598 Number of rooted ternary trees with n nodes; number of n-carbon alkyl radicals C(n)H(2n+1) ignoring stereoisomers.

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A000642 a(1)=0; for n>1, a(n) = number of isomeric hydrocarbons of the acetylene series with carbon content n.

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A121331 Number of bridged bicyclic skeletons with n carbon atoms (see Parks et al. for precise definition).

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A244399 Number of unlabeled rooted trees with n nodes and maximal outdegree (branching factor) 3.

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