A086194 -id:A086194 - 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

A000625 Number of n-node steric rooted ternary trees; number of n carbon alkyl radicals C(n)H(2n+1) taking stereoisomers into account.

Original entry on oeis.org

1, 1, 1, 2, 5, 11, 28, 74, 199, 551, 1553, 4436, 12832, 37496, 110500, 328092, 980491, 2946889, 8901891, 27012286, 82300275, 251670563, 772160922, 2376294040, 7333282754, 22688455980, 70361242924, 218679264772, 681018679604, 2124842137550, 6641338630714, 20792003301836

Offset: 0

N. J. A. Sloane

Nodes are unlabeled, each node has out-degree <= 3.
Steric, or including stereoisomers, means that the children of a node are taken in a certain cyclic order. If the children are rotated it is still the same tree, but any other permutation yields a different tree. See A000598 for the analogous sequence with stereoisomers not counted.
Other descriptions of this sequence: steric planted trees with n nodes; total number of monosubstituted alkanes C(n)H(2n+1)-X with n carbon atoms.
Let the entries in the nine columns of Blair and Henze's Table I (JACS 54 (1932), p. 1098) be denoted by Ps(n), Pn(n), Ss(n), Sn(n), Ts(n), Tn(n), As(n), An(n), T(n) respectively (here P = Primary, S = Secondary, T = Tertiary, s = stereoisomers, n = non-stereoisomers and the last column T(n) gives total).
Then Ps (and As) = A000620, Pn (and An, Sn) = A000621, Ss = A000622, Ts = A000623, Tn = A000624, T = this sequence. Recurrences generating these sequences are given in the Maple program in A000620.

J. K. Percus, Combinatorial Methods, Lecture Notes, 1967-1968, Courant Institute, New York University, 212pp. See pp. 64-65.
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..1930 (first 200 terms from T. D. Noe)
C. M. Blair and H. R. Henze, The number of stereoisomeric and non-stereoisomeric mono-substitution products of the paraffins, J. Amer. Chem. Soc., 54 (3) (1932), 1098-1106.
C. M. Blair and H. R. Henze, The number of stereoisomeric and non-stereoisomeric mono-substitution products of the paraffins, J. Amer. Chem. Soc., 54 (3) (1932), 1098-1105. (Annotated scanned copy)
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)
G. Polya, Algebraische Berechnung der Anzahl der Isomeren einiger organischer Verbindungen, Zeit. f. Kristall., 93 (1936), 415-443, Eq. (25).
G. Polya, Algebraische Berechnung der Anzahl der Isomeren einiger organischer Verbindungen, Zeit. f. Kristall., 93 (1936), 415-443, Eq. (25). (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. 44.
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)
Index entries for sequences related to rooted trees
Index entries for sequences related to trees

Cf. A000598, A000602, A000620-A000624, A000628, A010732, A010733, A086194, A086200, A239803, A239810.

A := 1; f := proc(n) global A; coeff(series( 1+(1/3)*x*(A^3+2*subs(x=x^3,A)), x, n+1), x, n); end; for n from 1 to 50 do A := series(A+f(n)*x^n,x,n +1); od: A;
A000625 := proc(n)
    local j,i,a ;
    option remember;
    if n <= 1 then
        1 ;
    else
        a :=0 ;
        for j from 1 to n-1 do
            a := a+ j*procname(j)*add(procname(i)*procname(n-j-i-1),i=0..n-j-1) ;
        end do:
        if modp(n-1,3) = 0 then
            a := a+2*(n-1)*procname((n-1)/3)/3 ;
        end if;
        a/ (n-1) ;
    end if;
end proc:
seq(A000625(n),n=0..30) ;

m = 31; c[0] = 1; gf[x_] = Sum[c[k] x^k, {k, 0, m}]; cc = Array[c, m]; coes = CoefficientList[ Series[gf[x] - 1 - (x*(gf[x]^3 + 2*gf[x^3])/3), {x, 0, m}], x] // Rest; Prepend[cc /. Solve[ Thread[ coes == 0], cc][[1]], 1]
(* Jean-François Alcover, Jun 24 2011 *)
a[0] = a[1] = 1; a[n_Integer] := a[n] = (Sum[j*a[j]*Sum[a[i]*a[n-i-j-1], {i, 0, n-j-1}], {j, 1, n-1}] + (2/3)*(n-1)*a[(n-1)/3])/(n-1); a[] = 0; Table[a[n], {n, 0, 31}] (* _Jean-François Alcover, Apr 21 2016, after Emeric Deutsch *)
terms = 32; A[] = 0; Do[A[x] = Normal[1 + x*(A[x]^3 + 2*A[x^3])/3 + O[x]^terms], terms]; CoefficientList[A[x], x] (* Jean-François Alcover, Apr 22 2016, updated Jan 11 2018 *)

a(n) = if(n, my(v=vector(n+1)); v[1]=1; v[2]=1; for(k=1, n-1, v[k+2] = sum(j=1, k, j*v[j+1]*(sum(i=0, k-j, v[i+1]*v[k-j-i+1])))/k + (2/3)*if(k%3, 0, v[k/3+1])); v[n+1], 1) \\ Jianing Song, Feb 17 2019

G.f. A(x) = 1 + x + x^2 + 2*x^3 + 5*x^4 + 11*x^5 + 28*x^6 + ... satisfies A(x) = 1 + x*(A(x)^3 + 2*A(x^3))/3.
a(0) = a(1) = 1; a(n+1) = 2*a(n/3)/3 + (Sum_{j=1..n} j*a(j)*(Sum_{i=1..n-j} a(i)*a(n-j-i)))/n for n >= 1, where a(k) = 0 if k not an integer (essentially eq (4) in the Robinson et al. paper). - Emeric Deutsch, May 16 2004
a(n) ~ c * b^n / n^(3/2), where b = 3.287112055584474991259... (see A239803), c = 0.346304267394183622435... (see A239810). - Vaclav Kotesovec, Mar 27 2014

Additional comments from Bruce Corrigan, Nov 04 2002

A000628 Number of n-node unrooted steric quartic trees; number of n-carbon alkanes C(n)H(2n+2) taking stereoisomers into account.

Original entry on oeis.org

1, 1, 1, 1, 2, 3, 5, 11, 24, 55, 136, 345, 900, 2412, 6563, 18127, 50699, 143255, 408429, 1173770, 3396844, 9892302, 28972080, 85289390, 252260276, 749329719, 2234695030, 6688893605, 20089296554, 60526543480, 182896187256, 554188210352, 1683557607211, 5126819371356, 15647855317080, 47862049187447, 146691564302648, 450451875783866, 1385724615285949

Offset: 0

N. J. A. Sloane

Trees are unrooted; nodes are unlabeled and have degree <= 4.
Regarding stereoisomers as different means that only the alternating group A_4 acts at each node, not the full symmetric group S_4. See A000602 for the analogous sequence when stereoisomers are not counted as different.
Has also been described as steric planted trees (paraffins) with n nodes.

F. Bergeron, G. Labelle and P. Leroux, Combinatorial Species and Tree-Like Structures, Camb. 1998, p. 290.
R. Davies and P. J. Freyd, C_{167}H_{336} is The Smallest Alkane with More Realizable Isomers than the Observable Universe has Particles, Journal of Chemical Education, Vol. 66, 1989, pp. 278-281.
J. L. Faulon, D. Visco and D. Roe, Enumerating Molecules, In: Reviews in Computational Chemistry Vol. 21, Ed. K. Lipkowitz, Wiley-VCH, 2005.
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).

Charles M. Blair and Henry R. Henze, The number of stereoisomeric and non-stereoisomeric paraffin hydrocarbons, J. Amer. Chem. Soc., 54 (1932), 1538-1545.
Charles M. Blair and Henry R. Henze, The number of stereoisomeric and non-stereoisomeric paraffin hydrocarbons, J. Amer. Chem. Soc., 54 (4) (1932), 1538-1545. (Annotated scanned copy)
L. Bytautats and D. J. Klein, Alkane Isomer Combinatorics: Stereostructure enumeration and graph-invariant and molecular-property distributions, J. Chem. Inf. Comput. Sci 39 (1999) 803-818, Table 1.
Lorentz Jäntschi and Lavinia-Lorena Pruteanu, Geometry of C_32 cyclic polyyne and some of its clusters, Carpathian J. Math. (2025) Vol. 41, No. 2, 371-391. See p. 371.
Pierre Leroux and Brahim Miloudi, Généralisations de la formule d'Otter, Ann. Sci. Math. Québec, Vol. 16, No. 1, pp. 53-80, 1992.
Pierre Leroux and Brahim Miloudi, Généralisations de la formule d'Otter, Ann. Sci. Math. Québec, Vol. 16, No. 1, pp. 53-80, 1992. (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. 44.
R. W. Robinson, F. Harary and A. T. Balaban, The numbers of chiral and achiral alkanes and monosubstituted alkanes, Tetrahedron 32 (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)
Index entries for sequences related to rooted trees
Index entries for sequences related to trees

Equals A000626 + A000627.

Cf. A000598, A000602, A000625, A010372, A010373, A086194, A086200.

s[0]:=1:s[1]:=1:for n from 0 to 60 do s[n+1/3]:=0 od:for n from 0 to 60 do s[n+2/3]:=0 od:for n from 0 to 60 do s[n+1/4]:=0 od:for n from 0 to 60 do s[n+1/2]:=0 od:for n from 0 to 60 do s[n+3/4]:=0 od:s[ -1]:=0:for n from 1 to 50 do s[n+1]:=(2*n/3*s[n/3]+sum(j*s[j]*sum(s[k]*s[n-j-k],k=0..n-j),j=1..n))/n od:for n from 0 to 50 do q[n]:=sum(s[i]*s[n-i],i=0..n) od:for n from 0 to 50 do q[n-1/2]:=0 od:for n from 0 to 40 do f:=n->(3*s[n]+2*s[n/2]+q[(n-1)/2]-q[n]+2*sum(s[j]*s[n-3*j-1],j=0..n/3))/4 od:seq(f(n),n=0..38); # the formulas for s[n+1] and f(n) are from eq.(4) and (12), respectively, of the Robinson et al. paper; s[n]=A000625(n), f(n)=A000628(n); q[n] is the convolution of s[n] with itself; # Emeric Deutsch

max = 40; s[0] = s[1] = 1; s[] = 0; For[n=1, n <= max, n++, s[n+1] = (2*n/3*s[n/3] + Sum[j*s[j]*Sum[s[k]*s[n-j-k], {k, 0, n-j}], {j, 1, n}])/n]; For[n=0, n <= max, n++, q[n] = Sum[s[i]*s[n-i], {i, 0, n}]]; For[n=0, n <= max, n++, q[n-1/2]=0]; f[n] := (3*s[n] + 2*s[n/2] + q[(n-1)/2] - q[n] + 2*Sum[s[j]*s[n-3*j-1], {j, 0, n/3}])/4; Table[f[n], {n, 0, max}] (* Jean-François Alcover, Dec 29 2014, after Emeric Deutsch *)

Blair and Henze give recurrence (see the Maple code).

For even n a(n) = A086194(n) + A086200(n/2), for odd n a(n) = A086194(n).

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

More terms from Emeric Deutsch, May 16 2004

A010372 Number of unrooted quartic trees with n (unlabeled) nodes and possessing a centroid; number of n-carbon alkanes C(n)H(2n +2) with a centroid ignoring stereoisomers.

Original entry on oeis.org

1, 0, 1, 1, 3, 2, 9, 8, 35, 39, 159, 202, 802, 1078, 4347, 6354, 24894, 38157, 148284, 237541, 910726, 1511717, 5731580, 9816092, 36797588, 64658432, 240215803, 431987953, 1590507121, 2917928218, 10660307791, 19910436898

Offset: 1

Paul Zimmermann, N. J. A. Sloane

The degree of each node is <= 4.
A centroid is a node with less than n/2 nodes in each of the incident subtrees, where n is the number of nodes in the tree. If a centroid exists it is unique.
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 A086194 for the analogous sequence with stereoisomers counted.

F. Harary, Graph Theory, p. 36, for definition of centroid.

A. Cayley, Über die analytischen Figuren, welche in der Mathematik Bäume genannt werden und ihre Anwendung auf die Theorie chemischer Verbindungen, Chem. Ber. 8 (1875), 1056-1059. (Annotated scanned copy)
E. M. Rains and N. J. A. Sloane, On Cayley's Enumeration of Alkanes (or 4-Valent Trees), J. Integer Sequences, Vol. 2 (1999), Article 99.1.1.
Index entries for sequences related to trees

Cf. A010373, A000022, A086194, A000598, A000602.

A000602(n) = a(n) + A010373(n/2) for n even, A000602(n) = a(n) for n odd.

with(combstruct): Alkyl := proc(n) combstruct[count]([ U,{U=Prod(Z,Set(U,card<=3))},unlabeled ],size=n) end:
centeredHC := proc(n) option remember; local f,k,z,f2,f3,f4; f := 1 + add(Alkyl(k)*z^k, k=0..iquo(n-1,2));
f2 := series(subs(z=z^2,f), z, n+1); f3 := series(subs(z=z^3,f), z, n+1); f4 := series(subs(z=z^4,f), z, n+1);
f := series(f*f3/3+f4/4+f2^2/8+f2*f^2/4+f^4/24, z, n+1); coeff(f, z, n-1) end: seq(centeredHC(n), n=1..32);

Description revised by Steve Strand (snstrand(AT)comcast.net), Aug 20 2003

A086200 Number of unrooted steric quartic trees with 2n (unlabeled) nodes and possessing a bicentroid; number of 2n-carbon alkanes C(2n)H(4n +2) with a bicentroid when stereoisomers are regarded as different.

Original entry on oeis.org

1, 3, 15, 66, 406, 2775, 19900, 152076, 1206681, 9841266, 82336528, 702993756, 6105180250, 53822344278, 480681790786, 4342078862605, 39621836138886, 364831810979041, 3386667673687950, 31669036266203766

Offset: 1

Steve Strand (snstrand(AT)comcast.net), Aug 28 2003

nonn

The degree of each node is <= 4.
A bicentroid is an edge which connects two subtrees of exactly m/2 nodes, where m is the number of nodes in the tree. If a bicentroid exists it is unique. Clearly trees with an odd number of nodes cannot have a bicentroid.
Regarding stereoisomers as different means that only the alternating group A_4 acts at each node, not the full symmetric group S_4. See A010373 for the analogous sequence when stereoisomers are not counted as different.

Cf. A000598, A000602, A010732, A010733, A000625, A000628, A086194.

For even n A000628(n) = A086194(n) + a(n/2), for odd n A000628(n) = A086194(n), since every tree has either a centroid or a bicentroid but not both.

G.f.: replace each term x in g.f. for A000625 by x(x+1)/2. Interpretation: ways to pick 2 specific radicals (order not important) from all n carbon radicals is number of 2n carbon bicentered alkanes (join the two radicals with an edge).

A036672 Number of stereoisomers of acyclic hydrocarbons with n carbon atoms.

Original entry on oeis.org

1, 3, 4, 13, 31, 109, 372, 1446, 5714, 23791, 100827, 438019, 1931818, 8648820, 39178079, 179383748, 828905252, 3861958783, 18125392905, 85631735301, 406977645228, 1944737525915, 9338989516911, 45051405221284, 218236995129380, 1061256971559421

Offset: 1

N. J. A. Sloane

nonn

Comment from Sean A. Irvine, edited by Natan Arie Consigli, Dec 26 2016 : (Start)
This is the counting series for the hypothetical stereo-isomers of all acyclic hydrocarbons that satisfy the octet rule.
A036673 is the variant with triple bonds excluded.
A002986 doesn't count stereoisomers.
The reference gives a three-variable generating function and cycle-index over A4 which can produce both these sequences. There are also dependencies on earlier generating functions.
(End)
Read has incorrect a(10)=27100. - Sean A. Irvine, Nov 20 2020

			From _M. F. Hasler_, Dec 26 2016: (Start)
For n = 1, there is only a(1) = 1 possibility, CH4.
For n = 2, one has C2H6 (ethane, H3C-CH3), C2H4 (ethylene, H2C=CH2 with a double bond), C2H2 (ethyne, HC≡CH, triple bond), whence a(2) = 3.
For n = 3, one has C3H8 (H3C-CH2-CH3), C3H6 (H2C=CH-CH3, propene), and two C3H4 (H2C=C=CH2, propadiene, and HC≡C-CH3: methylacetylene), thus a(3) = 4. Cyclic molecules like cyclopropane C3H6 and cyclopropropene C3H4 are excluded. (End)
From _Natan Arie Consigli_, Dec 26 2016: (Start)
For n = 4, we have butane, isobutane, 1-butene, cis/trans-2-butene, buta-1,2-diene, buta-1,3-diene, butatriene, isobutylene, but-1-yne, but-2-yne, diacetylene, but-1-en-3-yne.
For n = 5 we have:
- 3 alkanes: pentane, methylbutane and neopentane.
- 17 alkenes: 1-pentene, (E/Z)-2-pentene, 1,2-pentadiene, (E/Z)-1,3-pentadiene, 1,4-pentadiene, 1,2,3-petatriene, penta-1,2,4-triene, pentatetraene, 2-methylbut-1-ene, 2-methylbut-2-ene, 3-methylbut-1-ene, isoprene, 3-methylbuta-1,2-diene, (R/S)-penta-2,3-diene.
-11 alkynes: 1-pentyne, 2-pentyne, pent-1-en-4-yne, (E/Z)-pent-3-en-1-yne, penta-1,2-dien-4-yne, penta-1,4-diyne, penta-1,3-diyne, pent-1-en-3-yne, 3-methylbut-1-yne, 2-methylbut-1-en-3-yne. (End)

Sean A. Irvine, Correction of A036672(10) and A036673(10), 2020
Sean A. Irvine, Java program (github)
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. 60.
Wikipedia, Stereoisomerism

Cf. A000598-A000628, A002986, A010372, ..., A086194, ... A134818, ..., A173289, ..., A261336.

Cf. A107984, A036673.

a(10) corrected and more terms from Sean A. Irvine, Nov 20 2020

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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A000625 Number of n-node steric rooted ternary trees; number of n carbon alkyl radicals C(n)H(2n+1) taking stereoisomers into account.

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A000628 Number of n-node unrooted steric quartic trees; number of n-carbon alkanes C(n)H(2n+2) taking stereoisomers into account.

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A010372 Number of unrooted quartic trees with n (unlabeled) nodes and possessing a centroid; number of n-carbon alkanes C(n)H(2n +2) with a centroid ignoring stereoisomers.

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A086200 Number of unrooted steric quartic trees with 2n (unlabeled) nodes and possessing a bicentroid; number of 2n-carbon alkanes C(2n)H(4n +2) with a bicentroid when stereoisomers are regarded as different.

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A036672 Number of stereoisomers of acyclic hydrocarbons with n carbon atoms.

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